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Volumn 77, Issue 3, 2009, Pages 497-520

Synthetic nitroimidazoles: Biological activities and mutagenicity relationships

Author keywords

Anti HIV activity; Antibacterial; Antifungal; Antileishmanial agents; Antimycobacterial; Trypanocidal

Indexed keywords

2 AMINO 5 (1 METHYL 5 NITRO 2 IMIDAZOLYL) 1,3,4 THIADIAZOLE; 2 ETHYL 5 NITRO 2,3 DIHYDROIMIDAZO[2,1 B][1,3]OXAZOLE; 2,3 DIHYDRO 2 METHYL 6 NITRO 2 [4 [4 (4 TRIFLUOROMETHOXYPHENOXY) 1 PIPERIDINYL]PHENOXYMETHYL]IMIDAZO[2,1 B]OXAZOLE; 3 TERT BUTYL 2 HYDROXYPHENYL 5 NITRO 1 METHYL 2 IMIDAZOLYLCARBINOL; 5 NITRO 1 METHYLIMADAZOL 2 YL(2 HYDROXY 3 TERT BUTYLPHENYL)CARBINOL; 6,7 DIHYDRO 2 NITRO 6 (4 TRIFLUOROMETHOXYBENZYLOXY) 5H IMIDAZO[2,1 B][1,3]OXAZINE; AMPICILLIN; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ANTIINFECTIVE AGENT; ANTILEISHMANIAL AGENT; BENZNIDAZOLE; BIFONAZOLE; CGI 17341; DIIODOHYDROXYQUIN; ECONAZOLE; FLUNIDAZOLE; ISONIAZID; KETOCONAZOLE; METRONIDAZOLE; N [[3 (4 ACETYLPHENYL) 2 OXO 5 OXAZOLIDINYL]METHYL]ACETAMIDE; NIRIDAZOLE; NITROIMIDAZOLE DERIVATIVE; NORFLOXACIN; NYSTATIN; ORNIDAZOLE; RIFAMPICIN; RONIDAZOLE; SATRANIDAZOLE; STREPTOMYCIN; TINIDAZOLE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 70349298700     PISSN: 00368709     EISSN: 22180532     Source Type: Journal    
DOI: 10.3797/scipharm.0907-14     Document Type: Review
Times cited : (97)

References (113)
  • 1
    • 33644544741 scopus 로고    scopus 로고
    • The frequency of sister chromatid exchanges in cultured human peripheral blood lymphocyte treated with metronidazole in vitro
    • DOI 10.1080/01480540500408663
    • Celik A, Aras Ates N. The frequency of sister chromatid exchanges in cultured human peripheral blood lymphocyte treated with metronidazole in vitro. Drug Chem Toxicol. 2006; 29: 85-94. doi:10.1080/01480540500408663 (Pubitemid 43292237)
    • (2006) Drug and Chemical Toxicology , vol.29 , Issue.1 , pp. 85-94
    • Celik, A.1    Ates, N.A.2
  • 2
    • 0032939686 scopus 로고    scopus 로고
    • Efficacy of new 5-nitroimidazoles against metronidazole-susceptible and- Resistant Giardia, Trichomonas, and Entamoeba spp
    • Upcroft JA, Campbell RW, Benakli K, Upcroft P and Vanelle P. Efficacy of new 5-nitroimidazoles against metronidazole-susceptible and -resistant Giardia, Trichomonas, and Entamoeba spp. Antimicrob Agents Chemother. 1999; 43: 73-76. PMid:9869568 (Pubitemid 29069202)
    • (1999) Antimicrobial Agents and Chemotherapy , vol.43 , Issue.1 , pp. 73-76
    • Upcroft, J.A.1    Campbell, R.W.2    Benakli, K.3    Upcroft, P.4    Vanelle, P.5
  • 3
    • 0026448524 scopus 로고
    • Redox, radiation and reductive bioactivation
    • doi:10.2307/3578516
    • Adams GE. Redox, radiation and reductive bioactivation. Radiat Res. 1992; 132: 129-139. doi:10.2307/3578516
    • (1992) Radiat Res , vol.132 , pp. 129-139
    • Adams, G.E.1
  • 4
    • 0022590178 scopus 로고
    • Hypoxia-mediated nitroheterocyclic drugs in the radio- and chemotherapy of cancer
    • doi:10.1016/0006-2952(86)90560-5
    • Adams GE and Stratford IJ. Hypoxia-mediated nitroheterocyclic drugs in the radio- and chemotherapy of cancer. Biochem Pharmacol. 1986; 35: 71-76. doi:10.1016/0006-2952(86)90560-5
    • (1986) Biochem Pharmacol , vol.35 , pp. 71-76
    • Adams, G.E.1    Stratford, I.J.2
  • 5
    • 0028339820 scopus 로고
    • Bioreductive drugs for cancer therapy: The search for tumor specificity
    • PMid:8195012
    • Adams GE and Stratford IJ. Bioreductive drugs for cancer therapy: the search for tumor specificity. Int J Radiat Oncol Biol Phys. 1994; 29: 231-238. PMid:8195012
    • (1994) Int J Radiat Oncol Biol Phys , vol.29 , pp. 231-238
    • Adams, G.E.1    Stratford, I.J.2
  • 7
    • 0024819685 scopus 로고
    • Nitroimidazoles XXI 2,3-dihydro-6-nitroimidazo [2,1-b] oxazoles with anti-tubercular activity
    • doi:10.1016/0223-5234(89)90034-2
    • Nagarajan K, Shankar RG, Rajappa S, Shenoy ST, Costa-Pereira R. Nitroimidazoles XXI 2,3-dihydro-6-nitroimidazo [2,1-b] oxazoles with anti-tubercular activity. Eur J Med Chem. 1989; 24: 631-633. doi:10.1016/0223-5234(89)90034-2
    • (1989) Eur J Med Chem , vol.24 , pp. 631-633
    • Nagarajan, K.1    Shankar, R.G.2    Rajappa, S.3    Shenoy, S.T.4    Costa-Pereira, R.5
  • 8
    • 0342980850 scopus 로고    scopus 로고
    • 5-Nitroimidazole derivatives as possible antibacterial and antifungal agents
    • DOI 10.1016/S0014-827X(99)00109-3, PII S0014827X99001093
    • Gunay NS, Capan G, Ulusoy N, Ergenc N, Otuk G, Kaya D. 5-Nitroimidazole derivatives as possible antibacterial and antifungal agents. Farmaco. 1999; 54: 826-831. doi:10.1016/S0014-827X(99)00109-3 (Pubitemid 30009675)
    • (1999) Farmaco , vol.54 , Issue.11-12 , pp. 826-831
    • Gunay, N.S.1    Capan, G.2    Ulusoy, N.3    Ergenc, N.4    Otuk, G.5    Kaya, D.6
  • 9
    • 0037061639 scopus 로고    scopus 로고
    • Synthesis, biological evaluation, and binding mode of novel 1-[2-(diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles targeted at the HIV-1 reverse transcriptase
    • DOI 10.1021/jm010904a
    • Silvestri R, Artico M, De Martino G, Ragno R, Massa S, Loddo R, Murgioni C, Loi AG, LaColla P, Pani A. Synthesis, biological evaluation, and binding mode of novel 1-[2-(diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles targeted at the HIV-1 reverse transcriptase. J Med Chem. 2002; 45: 1567-1576. doi:10.1021/jm010904a (Pubitemid 34293523)
    • (2002) Journal of Medicinal Chemistry , vol.45 , Issue.8 , pp. 1567-1576
    • Silvestri, R.1    Artico, M.2    De Martino, G.3    Ragno, R.4    Massa, S.5    Loddo, R.6    Murgioni, C.7    Giulia Loi, A.8    La Colla, P.9    Pani, A.10
  • 10
    • 0034615103 scopus 로고    scopus 로고
    • 1-[2-(Diphenylmethoxy)ethyl]-2-methyl-5-nitroimidazole a potent lead for the design of novel NNRTIs
    • doi:10.1016/S0960-894X(99)00664-2
    • Silvestri R, Artico M, Massa S, Marceddu T, DeMontis F, LaColla P. 1-[2-(Diphenylmethoxy)ethyl]-2-methyl-5-nitroimidazole a potent lead for the design of novel NNRTIs. Bioorg Med Chem Lett. 2000; 10: 253-256. doi:10.1016/S0960-894X(99)00664-2
    • (2000) Bioorg Med Chem Lett , vol.10 , pp. 253-256
    • Silvestri, R.1    Artico, M.2    Massa, S.3    Marceddu, T.4    Demontis, F.5    LaColla, P.6
  • 11
    • 0031656984 scopus 로고    scopus 로고
    • Use of 2-nitroimidazoles as bioreductive markers for tumour hypoxia
    • Hodgkiss RJ. Use of 2-nitroimidazoles as bioreductive markers for tumour hypoxia. Anticancer Drug Res. 1998; 13: 687-702. PMid:9755725 (Pubitemid 28410155)
    • (1998) Anti-Cancer Drug Design , vol.13 , Issue.6 , pp. 687-702
    • Hodgkiss, R.J.1
  • 12
    • 0031105485 scopus 로고    scopus 로고
    • Design, synthesis, and biological activity of anti-angiogenic hypoxic cell radiosensitizer haloacetylcarbamoyl-2-nitroimidazoles
    • DOI 10.1016/S0968-0896(96)00274-X, PII S096808969600274X
    • Hori H, Jin CZ, Kiyono M, Kasai S, Shimamura M, Inayama S. Design, synthesis, and biological activity of anti-angiogenic hypoxic cell radiosensitizer haloacetylcarbamoyl-2-nitroimidazoles. Bioorg Med Chem. 1997; 5: 591-599. doi:10.1016/S0968-0896(96)00274-X (Pubitemid 27130087)
    • (1997) Bioorganic and Medicinal Chemistry , vol.5 , Issue.3 , pp. 591-599
    • Hori, H.1    Jin, C.-Z.2    Kiyono, M.3    Kasai, S.4    Shimamura, M.5    Inayama, S.6
  • 13
    • 0035083176 scopus 로고    scopus 로고
    • New antimetastatic hypoxic cell radiosensitizers: Design, synthesis, and biological activities of 2-nitroimidazole-acetamide, TX-1877, and its analogues
    • DOI 10.1016/S0968-0896(00)00265-0, PII S0968089600002650
    • Kasai S, Nagasawa H, Yamashita M, Masui M, Kuwasaka H, Oshodani T, Uto Y, Inomata T, Oka S, Inayamata S, Hori H. New antimetastatic hypoxic cell radiosensitizers: design, synthesis, and biological activities of 2-nitroimidazole-acetamide, TX-1877, and its analogues. Bioorg Med Chem. 2001; 9: 453-464. doi:10.1016/S0968-0896(00)00265-0 (Pubitemid 32244043)
    • (2001) Bioorganic and Medicinal Chemistry , vol.9 , Issue.2 , pp. 453-464
    • Kasai, S.1    Nagasawa, H.2    Yamashita, M.3    Masui, M.4    Kuwasaka, H.5    Oshodani, T.6    Uto, Y.7    Inomata, T.8    Oka, S.9    Inayama, S.10    Hori, H.11
  • 14
    • 2542525296 scopus 로고    scopus 로고
    • In vitro activity of Etanidazole against the protozoan parasite Trypanosoma cruzi
    • doi:10.1590/S0074-02762004000200021
    • Petray PB, Morilla MJ, Corral RS, Romero EL. In vitro activity of Etanidazole against the protozoan parasite Trypanosoma cruzi. Mem Inst Oswaldo Cruz. 2004; 99: 233-235. doi:10.1590/S0074-02762004000200021
    • (2004) Mem Inst Oswaldo Cruz , vol.99 , pp. 233-235
    • Petray, P.B.1    Morilla, M.J.2    Corral, R.S.3    Romero, E.L.4
  • 15
    • 2542525296 scopus 로고    scopus 로고
    • In vitro activity of Etanidazole against the protozoan parasite Trypanosoma cruzi
    • doi:10.1590/S0074-02762004000200021
    • Petray PB, Morilla MJ, Corral RS, Romero EL. In vitro activity of Etanidazole against the protozoan parasite Trypanosoma cruzi. Mem Inst Oswaldo Cruz. 2004; 99: 233-235. doi:10.1590/S0074-02762004000200021
    • (2004) Mem Inst Oswaldo Cruz , vol.99 , pp. 233-235
    • Petray, P.B.1    Morilla, M.J.2    Corral, R.S.3    Romero, E.L.4
  • 16
    • 77049163478 scopus 로고
    • A new antibiotic, azomycin
    • PMid:13152032
    • Maeda K, Osata T, Umezawa H. A new antibiotic, azomycin. J Antibiot. 1953; 6: 182. PMid:13152032
    • (1953) J Antibiot , vol.6 , pp. 182
    • Maeda, K.1    Osata, T.2    Umezawa, H.3
  • 17
    • 84965036986 scopus 로고
    • Activitéde l (hydroxy-2-ethyl)-1-methyl-2-nitro-5 imidazole (8,823 R.P.) vis-à-vis des infections experimentales Trichomonas vaginalis
    • PMid:13627590
    • Cosar C, Julou L. Activitéde l (hydroxy-2-ethyl)-1-methyl-2-nitro- 5 imidazole (8,823 R.P.) vis-à-vis des infections experimentales Trichomonas vaginalis. Ann Inst Pasteur. 1959; 96: 238-241. PMid:13627590
    • (1959) Ann Inst Pasteur , vol.96 , pp. 238-241
    • Cosar, C.1    Julou, L.2
  • 18
    • 0007594336 scopus 로고
    • Traitment de la giardiase (lambliase) par le metronidazole
    • PMid:13748230
    • Schneider J. Traitment de la giardiase (lambliase) par le metronidazole. Bull Soc Pathol Exot Filiales. 1961; 54: 84-93. PMid:13748230
    • (1961) Bull Soc Pathol Exot Filiales , vol.54 , pp. 84-93
    • Schneider, J.1
  • 19
    • 0014020820 scopus 로고
    • Metronidazole in amoebic dysentery and amoebic liver abscess
    • doi:10.1016/S0140-6736(66)92081-2
    • Powell SJ, Macleod L, Wilmot AJ, Elsdon-Dew R. Metronidazole in amoebic dysentery and amoebic liver abscess. Lancet. 1966; 288: 1329-1331. doi:10.1016/S0140-6736(66)92081-2
    • (1966) Lancet , vol.288 , pp. 1329-1331
    • Powell, S.J.1    Macleod, L.2    Wilmot, A.J.3    Elsdon-Dew, R.4
  • 20
    • 0016702845 scopus 로고
    • Clinical trials with metronidazole in human balantidiasis
    • PMid:1190365
    • Garcia-Leverde A, De Bonila L. Clinical trials with metronidazole in human balantidiasis. Am J Trop Med Hyg. 1975; 24: 781-783. PMid:1190365
    • (1975) Am J Trop Med Hyg , vol.24 , pp. 781-783
    • Garcia-Leverde, A.1    De Bonila, L.2
  • 21
    • 0028268373 scopus 로고
    • Resistance to the nitroheterocyclic drugs
    • doi:10.1016/0001-706X(94)90062-0
    • Townson SM, Boreham PFL, Upcroft P, Upcroft JA. Resistance to the nitroheterocyclic drugs. Acta Trop. 1994; 56: 173-194. doi:10.1016/0001-706X(94) 90062-0
    • (1994) Acta Trop , vol.56 , pp. 173-194
    • Townson, S.M.1    Boreham, P.F.L.2    Upcroft, P.3    Upcroft, J.A.4
  • 22
    • 0037460789 scopus 로고    scopus 로고
    • Amoebiasis
    • doi:10.1016/S0140-6736(03)12830-9
    • Stanley. SL Jr. Amoebiasis. Lancet. 2003; 361: 1025-1034. doi:10.1016/S0140-6736(03)12830-9
    • (2003) Lancet , vol.361 , pp. 1025-1034
    • Stanley Jr., S.L.1
  • 24
    • 0020536580 scopus 로고
    • Mode of action of metronidazole on anaerobic bacteria and protozoa
    • PMid:6849201
    • Müller M. Mode of action of metronidazole on anaerobic bacteria and protozoa. Surgery. 1983; 93: 165-171. PMid:6849201
    • (1983) Surgery , vol.93 , pp. 165-171
    • Müller, M.1
  • 25
    • 0022577790 scopus 로고
    • Reduction of nitroimidazoles in vitro and DNA damage
    • doi:10.1016/0006-2952(86)90554-X
    • Edwards DI. Reduction of nitroimidazoles in vitro and DNA damage. Biochem Pharmacol. 1986; 35: 53-58. doi:10.1016/0006-2952(86)90554-X
    • (1986) Biochem Pharmacol , vol.35 , pp. 53-58
    • Edwards, D.I.1
  • 26
    • 0142196033 scopus 로고    scopus 로고
    • Therapy of intestinal protozoa
    • doi:10.1016/j.pt.2003.09.003
    • Petri WA Jr. Therapy of intestinal protozoa. Trends Parasitol. 2003; 19: 523-526. doi:10.1016/j.pt.2003.09.003
    • (2003) Trends Parasitol , vol.19 , pp. 523-526
    • Petri Jr., W.A.1
  • 27
    • 0016688089 scopus 로고
    • Detection of mutagenic activity of metronidazole and niridazole in body fluids of humans and mice
    • doi:10.1126/science.766186
    • Legator MS, Connor TH, Stoeckel M. Detection of mutagenic activity of metronidazole and niridazole in body fluids of humans and mice. Science. 1975; 188: 1118-1119. doi:10.1126/science.766186
    • (1975) Science , vol.188 , pp. 1118-1119
    • Legator, M.S.1    Connor, T.H.2    Stoeckel, M.3
  • 28
    • 0015304363 scopus 로고
    • Induction of lung tumors and malignant lymphomas in mice by metronidazole
    • PMid:5058971
    • Rustia M, Shubik P. Induction of lung tumors and malignant lymphomas in mice by metronidazole. J Natl Cancer Inst. 1972; 48: 721-729. PMid:5058971
    • (1972) J Natl Cancer Inst , vol.48 , pp. 721-729
    • Rustia, M.1    Shubik, P.2
  • 29
    • 0015328010 scopus 로고
    • Current status of chemical carcinogenesis
    • doi:10.1073/pnas.69.4.1052
    • Shubik P. Current status of chemical carcinogenesis. Proc Natl Acad Sci U S A. 1972; 69: 1052-1055. doi:10.1073/pnas.69.4.1052
    • (1972) Proc Natl Acad Sci U S A , vol.69 , pp. 1052-1055
    • Shubik, P.1
  • 30
    • 0004217494 scopus 로고
    • VCH Publishers, Inc., Deerfield Beach, FL, and references cited therein
    • Boyer JH. Nitroazoles. VCH Publishers, Inc., Deerfield Beach, FL, 1986: 165-166 and references cited therein.
    • (1986) Nitroazoles , pp. 165-166
    • Boyer, J.H.1
  • 31
    • 0020327998 scopus 로고
    • The development of 5-nitroimidazoles for the treatment and prophylaxis of anaerobic bacterial infections
    • doi:10.1093/jac/10.suppl-A.23
    • Goldman P. The development of 5-nitroimidazoles for the treatment and prophylaxis of anaerobic bacterial infections. J Antimicrob Chemother. 1982; 10 (Suppl.): A23-A33. doi:10.1093/jac/10.suppl-A.23
    • (1982) J Antimicrob Chemother , vol.10 , Issue.SUPPL.
    • Goldman, P.1
  • 33
    • 0020050001 scopus 로고
    • Comparative efficacy of GO 10213 and some nitroimidazoles against Trichomonas vaginalis and T. foetus in mice infected subcutaneously
    • PMid:6979983
    • Ray DK, Chatterjee DK, Tendulkar JS. Comparative efficacy of GO 10213 and some nitroimidazoles against Trichomonas vaginalis and T. foetus in mice infected subcutaneously. Ann Trop Med Parasitol. 1982; 76: 175-178. PMid:6979983
    • (1982) Ann Trop Med Parasitol , vol.76 , pp. 175-178
    • Ray, D.K.1    Chatterjee, D.K.2    Tendulkar, J.S.3
  • 34
    • 0021708633 scopus 로고
    • A metronidazole-resistant strain of Trichomonas vaginalis and its sensitivity to GO 10213
    • doi:10.1093/jac/14.4.423
    • Ray DK, Tendulkar JS, Shrivastava VB, Datta AK, Nagarajan K. A metronidazole-resistant strain of Trichomonas vaginalis and its sensitivity to GO 10213. J Antimicrob Chemother. 1984; 14: 423-426. doi:10.1093/jac/14.4.423
    • (1984) J Antimicrob Chemother , vol.14 , pp. 423-426
    • Ray, D.K.1    Tendulkar, J.S.2    Shrivastava, V.B.3    Datta, A.K.4    Nagarajan, K.5
  • 35
    • 0022625993 scopus 로고
    • Antibacterial activity of GO 10213, a nitroimidazole derivative
    • Hof H, Stroder J. Antibacterial activity of GO 10213, a nitroimidazole derivative. Antimicrob Agents Chemother. 1986; 29: 953-954. PMid:3729357 (Pubitemid 16118350)
    • (1986) Antimicrobial Agents and Chemotherapy , vol.29 , Issue.5 , pp. 953-954
    • Hof, H.1    Stroder, J.2
  • 36
    • 0036965147 scopus 로고    scopus 로고
    • Synthesis and in vitro antimicrobial evaluation of 5-(1-methyl-5-nitro-2- imidazolyl)-4H-1, 2, 4-triazoles
    • doi:10.1002/ardp.200290004
    • Shafiee A, Sayadi A, Roozbahani MH, Foroumadi A, Kamal F. Synthesis and in vitro antimicrobial evaluation of 5-(1-methyl-5-nitro-2-imidazolyl)-4H-1, 2, 4-triazoles. Arch Pharm. 2002; 335: 495-499. doi:10.1002/ardp.200290004
    • (2002) Arch Pharm , vol.335 , pp. 495-499
    • Shafiee, A.1    Sayadi, A.2    Roozbahani, M.H.3    Foroumadi, A.4    Kamal, F.5
  • 37
    • 70349294616 scopus 로고
    • Uniquely non-mutagenic substituted nitroimidazole
    • US 4,728,664
    • Bagan ES, Miwa GT. Uniquely non-mutagenic substituted nitroimidazole. 1988 US 4,728,664.
    • (1988)
    • Bagan, E.S.1    Miwa, G.T.2
  • 38
    • 70349296235 scopus 로고
    • Non-mutagenic 1,2-disubstituted-4-nitroimidazole compounds useful as antiprotozoal agents
    • US 4,675, 337
    • Miwa GT, Wang Wen-Jen R, Walsh JS. Non-mutagenic 1,2-disubstituted-4- nitroimidazole compounds useful as antiprotozoal agents. 1987 US 4,675, 337.
    • (1987)
    • Miwa, G.T.1    Wang Wen-Jen, R.2    Walsh, J.S.3
  • 39
    • 70349276160 scopus 로고
    • 1-Methyl-5-nitro-imidazoline derivatives and therapeutic compositions which contain them as active principle
    • EP 0103100-A (8413)
    • Scalesiani JBA, Calle YB. 1-Methyl-5-nitro-imidazoline derivatives and therapeutic compositions which contain them as active principle. 1983 EP 0103100-A (8413).
    • (1983)
    • Scalesiani, J.B.A.1    Calle, Y.B.2
  • 40
    • 0023070361 scopus 로고
    • Structural alterations that differentially affect the mutagenic and antitrichomonal activities of 5-nitroimidazoles
    • Walsh JS, Wang R, Bagan E, Wang CC, Wislocki P, Miwa GT. Structural alterations that differentially affect the mutagenic and antitrichomonal activities of 5-nitroimidazoles. J Med Chem 1987; 30: 150-156. doi:10.1021/jm00384a025 (Pubitemid 17221631)
    • (1987) Journal of Medicinal Chemistry , vol.30 , Issue.1 , pp. 150-156
    • Walsh, J.S.1    Wang, R.2    Bagan, E.3
  • 41
    • 70349297795 scopus 로고
    • New 2-(1-alkyl-5-nitro)-imidazolyl-1-(2-hydroxy-5-alkyl)-phenyl carbinols, method for the preparation thereof and pharmaceutical compositions containing them
    • EP 111,657
    • Tessitore PT. New 2-(1-alkyl-5-nitro)-imidazolyl-1-(2-hydroxy-5-alkyl)- phenyl carbinols, method for the preparation thereof and pharmaceutical compositions containing them. 1983 EP 111,657.
    • (1983)
    • Tessitore, P.T.1
  • 42
    • 70349274619 scopus 로고
    • Antibacterial 5-Nitro-1-methyl-imidazolyl-3-terbutyl-2-hydroxy-aryl- carbinols
    • (Euroresearch S.R.L.) EP 535,528
    • Fudan D. Antibacterial 5-Nitro-1-methyl-imidazolyl-3-terbutyl-2-hydroxy- aryl-carbinols. (Euroresearch S.R.L.). 1992 EP 535,528.
    • (1992)
    • Fudan, D.1
  • 43
    • 0030572485 scopus 로고    scopus 로고
    • Preparation, antimicrobial evaluation and mutagenicity of differently substituted [2-hydroxyaryl]-[1-methyl-5-nitro-1H-2-imidazolyl]methanols
    • DOI 10.1016/0960-894X(96)00317-4
    • Arredondo Y, Moreno-Mafias M, Pleixats R, Palacin C, Raga MM, Castelló JM, Ortiz JA. Preparation, antimicrobial evaluation and mutagenicity of differently substituted [2-hydroxyaryl]-[1-methyl-5-nitro-1H-2- imidazolyl]methanols. Bioorg Med Chem Lett. 1996; 6: 1781-1784. doi:10.1016/0960-894X(96)00317-4 (Pubitemid 26253876)
    • (1996) Bioorganic and Medicinal Chemistry Letters , vol.6 , Issue.15 , pp. 1781-1784
    • Arredondo, Y.1    Moreno-Manas, M.2    Pleixats, R.3    Palacin, C.4    Raga, M.M.5    Castello, J.M.6    Ortiz, J.A.7
  • 44
    • 0027093649 scopus 로고
    • Antibacterial, antimycotic and trichomonicidal activity of a new nitroimidazole (EU 11100)
    • Dubini F, Riviera L, Cocuzza C, Bellotti MG. Antibacterial, antimycotic and trichomonicidal activity of a new nitroimidazole EU 11100. J Chemother. 1992; 4: 342-346. PMid:1287136 (Pubitemid 23030538)
    • (1992) Journal of Chemotherapy , vol.4 , Issue.6 , pp. 342-346
    • Dubini, F.1    Riviera, L.2    Cocuzza, C.3    Bellotti, M.G.4
  • 45
    • 35148820603 scopus 로고    scopus 로고
    • Synthesis, antibacterial activity, and quantitative structure-activity relationships of new (Z)-2-(nitroimidazolylmethylene)-3(2 H)-benzofuranone derivatives
    • DOI 10.1016/j.bmcl.2007.09.062, PII S0960894X07011158
    • Hadj-esfandiari N, Navidpour L, Shadnia H, Amini M, Samadi N, Faramarzi MA & Shafieea A. Synthesis, antibacterial activity, and quantitative structure-activity relationships of new (Z)-2-(nitroimidazolylmethylene)-3(2H)- benzofuranone derivatives. Bioorg Med Chem Lett. 2007; 17: 6354-6363. doi:10.1016/j.bmcl.2007.09.062 (Pubitemid 47552849)
    • (2007) Bioorganic and Medicinal Chemistry Letters , vol.17 , Issue.22 , pp. 6354-6363
    • Hadj-esfandiari, N.1    Navidpour, L.2    Shadnia, H.3    Amini, M.4    Samadi, N.5    Faramarzi, M.A.6    Shafiee, A.7
  • 48
    • 0032472923 scopus 로고    scopus 로고
    • Synthesis, metabolism and structure-mutagenicity relationships of novel 4-nitro-(imidazoles and pyrazoles) in Salmonella typhimurium
    • doi:10.1016/S0027-5107(97)00229-7
    • Hrelia P, Fimognari C, Maffei F, Brighenti B, Garuti L, Burnelli S, Cantelli-Forti G. Synthesis, metabolism and structure-mutagenicity relationships of novel 4-nitro-(imidazoles and pyrazoles) in Salmonella typhimurium. Mutat Res. 1998; 397: 293-301. doi:10.1016/S0027-5107(97)00229-7
    • (1998) Mutat Res , vol.397 , pp. 293-301
    • Hrelia, P.1    Fimognari, C.2    Maffei, F.3    Brighenti, B.4    Garuti, L.5    Burnelli, S.6    Cantelli-Forti, G.7
  • 49
    • 0033841374 scopus 로고    scopus 로고
    • Mutagenicity of nitroaromatic compounds
    • doi:10.1021/tx000002x
    • Purohit V, Basu AK. Mutagenicity of nitroaromatic compounds. Chem Res Toxicol. 2000; 8: 673-692. doi:10.1021/tx000002x
    • (2000) Chem Res Toxicol , vol.8 , pp. 673-692
    • Purohit, V.1    Basu, A.K.2
  • 50
    • 0026537779 scopus 로고
    • Evaluation of the mutagenic and genotoxic activities of 48 nitroimidazoles and related imidazole derivates by the Ames test and the SOS chromotest
    • PMid:1541258
    • De Méo M, Vanelle P, Bernadini E, Laget M, Maldonado J, Jentzer O, Crozet MP, Duménil G. Evaluation of the mutagenic and genotoxic activities of 48 nitroimidazoles and related imidazole derivates by the Ames test and the SOS chromotest. Environ Mol Mutagen. 1992; 19: 167-181. PMid:1541258
    • (1992) Environ Mol Mutagen , vol.19 , pp. 167-181
    • De Méo, M.1    Vanelle, P.2    Bernadini, E.3    Laget, M.4    Maldonado, J.5    Jentzer, O.6    Crozet, M.P.7    Duménil, G.8
  • 51
    • 13844323009 scopus 로고
    • Genotoxicity and carcinogenicity of metronidazole
    • Pmid:7515153
    • Dobiás L, Cerná M, Rössner P, Srám R. Genotoxicity and carcinogenicity of metronidazole. Environ Mutagen. 1994; 317: 177-194. Pmid:7515153
    • (1994) Environ Mutagen , vol.317 , pp. 177-194
    • Dobiás, L.1    Cerná, M.2    Rössner, P.3    Srám, R.4
  • 52
    • 47949097028 scopus 로고    scopus 로고
    • Synthesis and in vitro anti-Helicobacter pylori activity of N-[5-(5-nitro-2-heteroaryl)-1,3,4-thiadiazol-2-yl]thiomorpholines and related compounds
    • doi:10.1016/j.ejmech.2007.11.019
    • Mirzaei J, Siavoshi F, Emami S, Safari F, Khoshayand MR, Shafiee A, Foroumadi A. Synthesis and in vitro anti-Helicobacter pylori activity of N-[5-(5-nitro-2-heteroaryl)-1,3,4-thiadiazol-2-yl]thiomorpholines and related compounds. Eur J Med Chem. 2008; 43: 1575-1580. doi:10.1016/j.ejmech.2007.11.019
    • (2008) Eur J Med Chem , vol.43 , pp. 1575-1580
    • Mirzaei, J.1    Siavoshi, F.2    Emami, S.3    Safari, F.4    Khoshayand, M.R.5    Shafiee, A.6    Foroumadi, A.7
  • 53
    • 0025735930 scopus 로고
    • The in-vitro activity of drugs against Blastocystis hominis
    • doi:10.1093/jac/27.4.507
    • Dunn LA and Boreham PFL. The in-vitro activity of drugs against Blastocystis hominis. J Antimicrob Chemother. 1991; 27: 507-516. doi:10.1093/jac/27.4.507
    • (1991) J Antimicrob Chemother , vol.27 , pp. 507-516
    • Dunn, L.A.1    Boreham, P.F.L.2
  • 54
    • 0342980850 scopus 로고    scopus 로고
    • 5-Nitroimidazole derivatives as possible antibacterial and antifungal agents
    • DOI 10.1016/S0014-827X(99)00109-3, PII S0014827X99001093
    • Gunay NS, Capan G, Ulusoy N, Ergenc N, Otuk G and Kaya D. Nitroimidazole derivatives as possible antibacterial and antifungal agents. Farmaco. 1999; 54: 826-831. doi:10.1016/S0014-827X(99)00109-3 (Pubitemid 30009675)
    • (1999) Farmaco , vol.54 , Issue.11-12 , pp. 826-831
    • Gunay, N.S.1    Capan, G.2    Ulusoy, N.3    Ergenc, N.4    Otuk, G.5    Kaya, D.6
  • 55
    • 0032833154 scopus 로고    scopus 로고
    • Antituberculosis activity of certain antifungal and antihelmintic drugs
    • DOI 10.1054/tuld.1999.0212
    • Sun Z and Zhang Y. Antituberculosis activity of certain antifungal and antihelmintic drugs. Tub Lung Dis. 1999; 79: 319-320. doi:10.1054/tuld.1999.0212 (Pubitemid 29479132)
    • (1999) Tubercle and Lung Disease , vol.79 , Issue.5 , pp. 319-320
    • Sun, Z.1    Zhang, Y.2
  • 56
    • 60149101405 scopus 로고    scopus 로고
    • Synthesis of some N-substituted nitroimidazole derivatives as potential antioxidant and antifungal agents
    • doi:10.1016/j.ejmech.2008.05.016
    • Olender D, Zwawiak J, Lukianchuk V, Lesyk R, Kropacz A, Fojutowski A, Zaprutko L. Synthesis of some N-substituted nitroimidazole derivatives as potential antioxidant and antifungal agents. Eur J Med Chem. 2009; 44: 645-652. doi:10.1016/j.ejmech.2008.05.016
    • (2009) Eur J Med Chem , vol.44 , pp. 645-652
    • Olender, D.1    Zwawiak, J.2    Lukianchuk, V.3    Lesyk, R.4    Kropacz, A.5    Fojutowski, A.6    Zaprutko, L.7
  • 57
    • 0015619875 scopus 로고
    • New 5-substituted 1-alkyl-2-nitroimidazoles
    • doi:10.1021/jm00263a035
    • Cavalleri B, Ballotta R, Arioli V, Lancini G. New 5-substituted 1-alkyl-2-nitroimidazoles. J Med Chem. 1973; 16: 557-560. doi:10.1021/ jm00263a035
    • (1973) J Med Chem , vol.16 , pp. 557-560
    • Cavalleri, B.1    Ballotta, R.2    Arioli, V.3    Lancini, G.4
  • 58
    • 0017656029 scopus 로고
    • Synthesis and biological activity of some vinyl substituted 2 nitroimidazoles
    • Cavalleri B, Volpe G, Arioli V. Synthesis and biological activity of some vinyl-substituted 2-nitroimidazoles. J Med Chem. 1977; 20: 656-660. doi:10.1021/jm00215a007 (Pubitemid 8095437)
    • (1977) Journal of Medicinal Chemistry , vol.20 , Issue.5 , pp. 656-660
    • Cavalleri, B.1    Volpe, G.2    Arioli, V.3
  • 59
    • 0017736090 scopus 로고
    • Synthesis and biological activity of some 2-aminoimidazoles
    • PMid:579099
    • Cavalleri B, Volpe G, Arioli V, Parenti F. Synthesis and biological activity of some 2-aminoimidazoles. Arzneimittelforschung. 1977; 27: 1889-1895. PMid:579099
    • (1977) Arzneimittelforschung , vol.27 , pp. 1889-1895
    • Cavalleri, B.1    Volpe, G.2    Arioli, V.3    Parenti, F.4
  • 60
    • 0017756455 scopus 로고
    • 1-Methyl-2-nitroimidazol-5-yl derivatives. IIIrd communication
    • PMid:578425
    • Cavalleri B, Volpe G, Ripamonti A, Arioli V. 1-Methyl-2-nitroimidazol-5- yl derivatives. IIIrd communication. Arzneimittelforschung. 1977; 27: 1131-1134. PMid:578425
    • (1977) Arzneimittelforschung , vol.27 , pp. 1131-1134
    • Cavalleri, B.1    Volpe, G.2    Ripamonti, A.3    Arioli, V.4
  • 61
    • 0017656314 scopus 로고
    • 1-Methyl-2-nitroimidazol-5-yl derivatives. IVth Communication
    • PMid:332192
    • Cavalleri B, Volpe G, Arioli V, Lancini GC. 1-Methyl-2-nitroimidazol-5-yl derivatives. IVth Communication. Arzneimittelforschung. 1977; 27: 1391-1392. PMid:332192
    • (1977) Arzneimittelforschung , vol.27 , pp. 1391-1392
    • Cavalleri, B.1    Volpe, G.2    Arioli, V.3    Lancini, G.C.4
  • 62
    • 0011767336 scopus 로고
    • Novel nitroimidazo[2,1-b] oxazole formation from reaction of 2, 4(5)-dinitroimidazole with oxiranes (1)
    • doi:10.1002/jhet.5570160743
    • Sehgal RK, Agrawal KC. Novel nitroimidazo[2,1-b] oxazole formation from reaction of 2, 4(5)-dinitroimidazole with oxiranes (1). J Heterocyclic Chem. 1979; 16: 1499-1500. doi:10.1002/jhet.5570160743
    • (1979) J Heterocyclic Chem , vol.16 , pp. 1499-1500
    • Sehgal, R.K.1    Agrawal, K.C.2
  • 64
    • 41149173349 scopus 로고    scopus 로고
    • Synthesis and antitubercular activity of 7-(R)- And 7-(S)-methyl-2-nitro- 6-(S)-(4-(trifluoromethoxy)benzyloxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3] oxazines, analogues of PA-824
    • doi:10.1016/j.bmcl.2008.03.011
    • Li X, Manjunatha UH, Goodwin MB, Knox JE, Lipinski CA, Keller TH, Barry CE III and Dowd CS. Synthesis and antitubercular activity of 7-(R)- and 7-(S)-methyl-2-nitro-6-(S)-(4-(trifluoromethoxy)benzyloxy)-6, 7-dihydro-5H-imidazo[2,1-b][1,3]oxazines, analogues of PA-824. Bioorg Med Chem Lett. 2008; 18: 2256-2262. doi:10.1016/j.bmcl.2008.03.011
    • (2008) Bioorg Med Chem Lett , vol.18 , pp. 2256-2262
    • Li, X.1    Manjunatha, U.H.2    Goodwin, M.B.3    Knox, J.E.4    Lipinski, C.A.5    Keller, T.H.6    Barry III, C.E.7    Dowd, C.S.8
  • 65
    • 33845323336 scopus 로고    scopus 로고
    • OPC-67683, a Nitro-Dihydro-Imidazooxazole derivative with promising action against tuberculosis in vitro and in mice
    • doi:10.1371/journal.pmed.0030466
    • Matsumoto M, Hashizume H, Tomishige T, Kawasaki M, Tsubouchi H, Sasaki H, Shimokawa Y, Komatsu M. OPC-67683, a Nitro-Dihydro-Imidazooxazole derivative with promising action against tuberculosis in vitro and in mice. PLoS Med. 2006; 3: 2131-2144. doi:10.1371/journal.pmed.0030466
    • (2006) PLoS Med , vol.3 , pp. 2131-2144
    • Matsumoto, M.1    Hashizume, H.2    Tomishige, T.3    Kawasaki, M.4    Tsubouchi, H.5    Sasaki, H.6    Shimokawa, Y.7    Komatsu, M.8
  • 67
    • 4644371358 scopus 로고    scopus 로고
    • Prospects for clinical introduction of nitroimidazole antibiotics for the treatment of tuberculosis
    • doi:10.2174/1381612043383214
    • Barry CE III, Boshoff HI, Dowd CS. Prospects for clinical introduction of nitroimidazole antibiotics for the treatment of tuberculosis. Curr Pharm Des. 2004; 10: 3239-3262. doi:10.2174/1381612043383214
    • (2004) Curr Pharm Des , vol.10 , pp. 3239-3262
    • Barry III, C.E.1    Boshoff, H.I.2    Dowd, C.S.3
  • 68
    • 0034669750 scopus 로고    scopus 로고
    • Bactericidal and inhibitory effects of azole antifungal compounds on Mycobacterium smegmatis
    • doi:10.1111/j.1574-6968.2000.tb09375.x
    • Jackson CJ, Lamb DC, Kelly DE, Kelly SL. Bactericidal and inhibitory effects of azole antifungal compounds on Mycobacterium smegmatis. FEMS Microbiol Lett. 2000; 192: 159-162. doi:10.1111/j.1574-6968.2000.tb09375.x
    • (2000) FEMS Microbiol Lett , vol.192 , pp. 159-162
    • Jackson, C.J.1    Lamb, D.C.2    Kelly, D.E.3    Kelly, S.L.4
  • 69
    • 0037397783 scopus 로고    scopus 로고
    • Synthesis and antifungal activity of (+/-)-1-(5-aryl-3-pyridin-2-yl-4,5- dihydro-pyrazol-1-yl)-2-imidazol-1-yl-ethanone. derivatives
    • doi:10.1016/S0014-827X(02)00006-X
    • Mamolo MG, Zampieri D, Falagiani V, Vio L, Banfi E. Synthesis and antifungal activity of (+/-)-1-(5-aryl-3-pyridin-2-yl-4,5-dihydro-pyrazol-1-yl)- 2-imidazol-1-yl-ethanone. derivatives. Farmaco. 2003; 58: 315-322. doi:10.1016/S0014-827X(02)00006-X
    • (2003) Farmaco , vol.58 , pp. 315-322
    • Mamolo, M.G.1    Zampieri, D.2    Falagiani, V.3    Vio, L.4    Banfi, E.5
  • 70
    • 4644237403 scopus 로고    scopus 로고
    • Synthesis and anti-tuberculosis activity of N-aryl-C-nitroazoles
    • doi:10.1016/j.ejmech.2004.06.014
    • Walczak K, Gondela A, Suwinski J. Synthesis and anti-tuberculosis activity of N-aryl-C-nitroazoles. Eur J Med Chem. 2004; 39: 849-853. doi:10.1016/j.ejmech.2004.06.014
    • (2004) Eur J Med Chem , vol.39 , pp. 849-853
    • Walczak, K.1    Gondela, A.2    Suwinski, J.3
  • 71
    • 16544387783 scopus 로고    scopus 로고
    • Antituberculosis Agents X. Synthesis and evaluation of in vitro antituberculosis activity of 2-(5-nitro-2-furyl)- and 2-(1-methyl-5-nitro-1H- imidazol-2-yl)-1,3,4-thiadiazole Derivatives
    • doi:10.1007/BF02980122
    • Foroumadi A, Soltani F, Jabini R, Moshafi MH, Rasnani FM. Antituberculosis Agents X. Synthesis and evaluation of in vitro antituberculosis activity of 2-(5-nitro-2-furyl)- and 2-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,3, 4-thiadiazole Derivatives. Arch Pharm Res. 2004; 27: 502-506. doi:10.1007/BF02980122
    • (2004) Arch Pharm Res , Issue.27 , pp. 502-506
    • Foroumadi, A.1    Soltani, F.2    Jabini, R.3    Moshafi, M.H.4    Rasnani, F.M.5
  • 72
    • 0035425315 scopus 로고    scopus 로고
    • Antituberculosis agents II: Evaluation of in vitro antituberculosis activity and cytotoxicity of some 2-(1-methyl-5-nitro-2-imidazolyl)-1,3,4- thiadiazole derivatives
    • doi:10.1016/S0014-827X(01)01099-0
    • Foroumadi, A.; Mirzaei, M.; Shafiee A. Antituberculosis agents II: Evaluation of in vitro antituberculosis activity and cytotoxicity of some 2-(1-methyl-5-nitro-2-imidazolyl)-1,3,4-thiadiazole derivatives. Farmaco. 2001; 56: 621-623. doi:10.1016/S0014-827X(01)01099-0
    • (2001) Farmaco , Issue.56 , pp. 621-623
    • Foroumadi, A.1    Mirzaei, M.2    Shafiee, A.3
  • 73
    • 34047273190 scopus 로고    scopus 로고
    • Trypanocidal nitroimidazole derivatives: Relationships among chemical structure and genotoxic activity
    • DOI 10.1016/j.bcp.2007.01.024, PII S0006295207000573
    • Buschini A, Giordani F, Northfleet de Albuquerque C, Pellacani C, Pelosi G, Rossi C, Araujo TM, Zucchi D, Poli P. Trypanocidal nitroimidazole derivatives: Relationships among chemical structure and genotoxic activity. Biochem Pharmacol. 2007; 73: 1537-1547. doi:10.1016/j.bcp.2007.01.024 (Pubitemid 46546382)
    • (2007) Biochemical Pharmacology , vol.73 , Issue.10 , pp. 1537-1547
    • Buschini, A.1    Giordani, F.2    De Albuquerque, C.N.3    Pellacani, C.4    Pelosi, G.5    Rossi, C.6    Zucchi, T.M.A.D.7    Poli, P.8
  • 74
    • 0028973387 scopus 로고
    • Effect of megazol on Trypanosoma brucei brucei acute and subacute infections in Swiss mice
    • doi:10.1016/0001-706X(95)00109-R
    • Bouteille B, Marie-Daragon A, Chauvière G, De Albuquerque C, Enanga B, Darde M-L et al. Effect of megazol on Trypanosoma brucei brucei acute and subacute infections in Swiss mice. Acta Trop. 1995; 60: 73-80. doi:10.1016/0001-706X(95)00109-R
    • (1995) Acta Trop , vol.60 , pp. 73-80
    • Bouteille, B.1    Marie-Daragon, A.2    Chauvière, G.3    De Albuquerque, C.4    Enanga, B.5    Darde, M.-L.6
  • 75
    • 0031658497 scopus 로고    scopus 로고
    • Megazol combined with suramin: A chemotherapy regimen which reversed the CNS pathology in a model of human African trypanosomiasis in mice
    • Enanga B, Keita M, Chauviere G, Dumas M, Bouteille B. Megazol combined with suramin: a chemotherapy regimen which reversed the CNS pathology in a model of human African trypanosomiasis in mice. Trop Med Int Health. 1998; 3: 736-741. PMid:9754669 (Pubitemid 28450437)
    • (1998) Tropical Medicine and International Health , vol.3 , Issue.9 , pp. 736-741
    • Enanga, B.1    Keita, M.2    Chauviere, G.3    Dumas, M.4    Bouteille, B.5
  • 78
    • 0016813184 scopus 로고
    • The mutagenic action of nitroimidazoles. II. Effects of 2-nitroimidazoles
    • doi:10.1016/0165-1161(75)90083-7
    • Voogd CE, Van der Stel JJ, Jacobs JJ. The mutagenic action of nitroimidazoles. II. Effects of 2-nitroimidazoles. Mutat Res. 1975; 31: 149-152. doi:10.1016/0165-1161(75)90083-7
    • (1975) Mutat Res , vol.31 , pp. 149-152
    • Voogd, C.E.1    Van Der Stel, J.J.2    Jacobs, J.J.3
  • 79
    • 0025087052 scopus 로고
    • Screening the mutagenic activities of commonly used antiparasite drugs by the Simultes, a simplified Salmonella/microsome plate incorporation assay
    • doi:10.1590/S0036-46651990000400006
    • Melo ME, Ferreira LC. Screening the mutagenic activities of commonly used antiparasite drugs by the Simultes, a simplified Salmonella/microsome plate incorporation assay. Rev Inst Med Trop Sao Paulo. 1990; 32: 269-274. doi:10.1590/S0036-46651990000400006
    • (1990) Rev Inst Med Trop Sao Paulo , vol.32 , pp. 269-274
    • Melo, M.E.1    Ferreira, L.C.2
  • 80
    • 0033291566 scopus 로고    scopus 로고
    • Implication du megasol dans la chimiotherapie des trypanosomosis
    • PMid:10816740
    • Bouteille B, Chauvière G. Implication du megasol dans la chimiotherapie des trypanosomosis. Med Trop. 1999; 59: 321-330. PMid:10816740
    • (1999) Med Trop , vol.59 , pp. 321-330
    • Bouteille, B.1    Chauvière, G.2
  • 81
    • 0021401673 scopus 로고
    • Free radical metabolites in the mode of action of chemotherapeutic agents and phagocytic cells on Trypanosoma cruzi
    • PMid:6328615
    • Docampo R, Moreno SN. Free radical metabolites in the mode of action of chemotherapeutic agents and phagocytic cells on Trypanosoma cruzi. Rev Infect Dis. 1984; 6: 223-238. PMid:6328615
    • (1984) Rev Infect Dis , vol.6 , pp. 223-238
    • Docampo, R.1    Moreno, S.N.2
  • 83
    • 2442472289 scopus 로고    scopus 로고
    • In vitro and in vivo chromosomal aberrations induced by megazol
    • doi:10.1016/j.mrgentox.2004.02.013
    • Nesslany F, Brugier S, Mouries MA, Le Curieux F, Marzin D. In vitro and in vivo chromosomal aberrations induced by megazol. Mutat Res. 2004; 560: 147-158. doi:10.1016/j.mrgentox.2004.02.013
    • (2004) Mutat Res , vol.560 , pp. 147-158
    • Nesslany, F.1    Brugier, S.2    Mouries, M.A.3    Le Curieux, F.4    Marzin, D.5
  • 84
    • 0022604437 scopus 로고
    • CL 64,855, a potent anti-Trypanosoma cruzi drug, is also mutagenic in the Salmonella/microsome assay
    • doi:10.1590/S0074-02761986000100006
    • Ferreira RC, Ferreira LC. CL 64,855, a potent anti-Trypanosoma cruzi drug, is also mutagenic in the Salmonella/microsome assay. Mem Inst Oswaldo Cruz. 1986; 81: 49-52. doi:10.1590/S0074-02761986000100006
    • (1986) Mem Inst Oswaldo Cruz , Issue.81 , pp. 49-52
    • Ferreira, R.C.1    Ferreira, L.C.2
  • 86
    • 0019724801 scopus 로고
    • Evidence for the existence of a family of bacterial nitroreductases capable of activating nitrated polycyclics to mutagens
    • DOI 10.1002/em.2860030403
    • McCoy EC, Rosenkranz HR, Mermelstein R. Evidence for the existence of a family of bacterial nitroreductases capable of activating nitrated polycyclics to mutagens. Environ Mol Mutagen. 1981; 3: 421-427. doi:10.1002/em.2860030403 (Pubitemid 11005379)
    • (1981) Environmental Mutagenesis , vol.3 , Issue.4 , pp. 421-427
    • McCoy, E.C.1    Rosenkranz, H.S.2    Mermelstein, R.3
  • 87
    • 0022336954 scopus 로고
    • Dinitropyrene-resistant Salmonella typhimurium are deficient in n acetyl-CoA-acetyl-transferase
    • doi:10.1016/S0009-2797(85)80169-1
    • Orr JC, Bryant DW, McCalla DR, Quilliam MA. Dinitropyrene-resistant Salmonella typhimurium are deficient in n acetyl-CoA-acetyl-transferase. Chem Biol Interact. 1985; 54: 281-288. doi:10.1016/S0009-2797(85)80169-1
    • (1985) Chem Biol Interact , vol.54 , pp. 281-288
    • Orr, J.C.1    Bryant, D.W.2    McCalla, D.R.3    Quilliam, M.A.4
  • 88
    • 0026611862 scopus 로고
    • 2-receptor agonists. Synthesis, in vitro pharmacology, and qualitative structure-activity relationships of substituted 4-and 5-(2-aminoethyl) thiazoles
    • doi:10.1021/jm00095a021
    • 2-receptor agonists. Synthesis, in vitro pharmacology, and qualitative structure-activity relationships of substituted 4-and 5-(2-aminoethyl) thiazoles. J Med Chem. 1992; 35: 3239-3246. doi:10.1021/jm00095a021
    • (1992) J Med Chem , vol.35 , pp. 3239-3246
    • Erik, J.C.1    Vander Goot, H.2    Sterk, G.J.3    Timmerman, H.4
  • 89
    • 0033535529 scopus 로고    scopus 로고
    • Synthesis and in vitro pharmacology of a series of new chiral histamine H3-receptor ligands: 2-(R and S)-amino-3-(1H-imidazol-4(5)-yl) propyl ether derivatives
    • doi:10.1021/jm980408v
    • Kovalainen JT, Christiaans JAM, Kotisaari S, Laitinen JT, Männistö PT, Tuomisto L, Gynther J. Synthesis and in vitro pharmacology of a series of new chiral histamine H3-receptor ligands: 2-(R and S)-amino-3-(1H-imidazol-4(5)-yl) propyl ether derivatives. J Med Chem. 1999; 42: 1193-1202. doi:10.1021/jm980408v
    • (1999) J Med Chem , vol.42 , pp. 1193-1202
    • Kovalainen, J.T.1    Christiaans, J.A.M.2    Kotisaari, S.3    Laitinen, J.T.4    Männistö, P.T.5    Tuomisto, L.6    Gynther, J.7
  • 90
    • 0032478798 scopus 로고    scopus 로고
    • p38 Mitogen-activated protein kinase-dependent and -independent intracellular signal transduction pathways leading to apoptosis in human neutrophils
    • doi:10.1074/jbc.273.14.8389
    • Farsch SC, Nick JA, Fadok VA, Bratton DL, Worthen GS, Henson PM. p38 Mitogen-activated protein kinase-dependent and -independent intracellular signal transduction pathways leading to apoptosis in human neutrophils. J Biol Chem. 1998; 273: 8389-8397. doi:10.1074/jbc.273.14.8389
    • (1998) J Biol Chem , vol.273 , pp. 8389-8397
    • Farsch, S.C.1    Nick, J.A.2    Fadok, V.A.3    Bratton, D.L.4    Worthen, G.S.5    Henson, P.M.6
  • 93
    • 0018373569 scopus 로고
    • Structure-activity relationships in the development of hypoxic cell radiosensitizers. I. Sensitization efficiency
    • Adams GE, Clarke ED, Flockhart IR, Jacobs RS, Sehmi DS, Stratford P, Wardman IJ, Watts ME, Parrick J, Wallace RG, Smithen CE. Structure-activity relationships in the development of hypoxic cell radiosensitizers I. Sensitization efficiency. Int J Radiat Biol Relat Stud Phys Chem Med. 1979; 35: 133-150. PMid:312783 (Pubitemid 9111460)
    • (1979) International Journal of Radiation Biology , vol.35 , Issue.2 , pp. 133-150
    • Adams, G.E.1    Clarke, E.D.2    Flockhart, I.R.3
  • 94
    • 0023276353 scopus 로고
    • Distribution of nitroimidazoles and L-phenylalanine mustard in mammary adenocarcinoma 16/C tumors
    • DOI 10.1007/BF00570482
    • Noker P, Simpson-Herren L, Wagoner SD. Distribution of nitroimidazoles and L-phenylalanine mustard in mammary adenocarcinoma 16/C tumors. Cancer Chemother Pharm. 1987; 20: 188-192. PMid:3677296 (Pubitemid 17163391)
    • (1987) Cancer Chemotherapy and Pharmacology , vol.20 , Issue.3 , pp. 188-192
    • Noker, P.E.1    Simpson-Herren, L.2    Wagoner, S.D.3
  • 95
    • 34848870695 scopus 로고    scopus 로고
    • Synthesis and anti-HIV evaluation of new 5-substituted piperazinyl-4-nitroimidazole derivatives
    • doi:10.2478/v10007-007-0031-7
    • Al-Soud YA, Al-Masoudi NA, Hassan HG, Clercq ED, Pannecouque C. Nitroimidazoles. V. Synthesis and anti-HIV evaluation of new 5-substituted piperazinyl-4-nitroimidazole derivatives. Acta Pharm. 2007; 57: 379-393. doi:10.2478/v10007-007-0031-7
    • (2007) Acta Pharm , vol.57 , pp. 379-393
    • Al-Soud, Y.A.1    Al-Masoudi, N.A.2    Hassan, H.G.3    Clercq, E.D.4    Pannecouque, C.5    Nitroimidazoles, V.6
  • 96
    • 0034615103 scopus 로고    scopus 로고
    • 1-[2-(diphenylmethoxy)ethyl]-2-methyl-5-nitroimidazole: A potent lead for the design of novel NNRTIs
    • doi:10.1016/S0960-894X(99)00664-2
    • Silvestri R, Artico M, Massa S, Marceddu T, Montis F De and Colla P La. 1-[2-(diphenylmethoxy)ethyl]-2-methyl-5-nitroimidazole: a potent lead for the design of novel NNRTIs. Bioorg Med Chem Lett. 2000; 10: 253-256. doi:10.1016/S0960-894X(99)00664-2
    • (2000) Bioorg Med Chem Lett , vol.10 , pp. 253-256
    • Silvestri, R.1    Artico, M.2    Massa, S.3    Marceddu, T.4    De Montis, F.5    La Colla, P.6
  • 98
    • 61349161162 scopus 로고    scopus 로고
    • Nitroimidazolyl-1,3,4-thiadiazole-based anti-leishmanial agents: Synthesis and in vitro biological evaluation
    • doi:10.1016/j.ejmech.2008.03.039
    • Poorrajab F, Ardestani SK, Emami S, Behrouzi-Fardmoghadam M, Shafiee A, Foroumadi, A. Nitroimidazolyl-1,3,4-thiadiazole-based anti-leishmanial agents: Synthesis and in vitro biological evaluation. Eur J Med Chem. 2009; 44: 1758-1762. doi:10.1016/j.ejmech.2008.03.039
    • (2009) Eur J Med Chem , vol.44 , pp. 1758-1762
    • Poorrajab, F.1    Ardestani, S.K.2    Emami, S.3    Behrouzi-Fardmoghadam, M.4    Shafiee, A.5    Foroumadi, A.6
  • 99
    • 0028632781 scopus 로고
    • Clinical evaluation of nitroimidazoles as modifiers of hypoxia in solid tumors
    • PMid:7620219
    • Overgaard J. Clinical evaluation of nitroimidazoles as modifiers of hypoxia in solid tumors. Oncol Res. 1994; 6: 509-518. PMid:7620219
    • (1994) Oncol Res , vol.6 , pp. 509-518
    • Overgaard, J.1
  • 100
    • 0028106216 scopus 로고
    • Mechanism of the selective hypoxic cytotoxicity of 1-methyl-2- Nitroimidazole
    • DOI 10.1016/0006-2952(94)90108-2
    • Brezden CB, McClelland RA and Rauth AM. Mechanism of the selective hypoxic cytotoxicity of 1-methyl-2-nitroimidazole. Biochem Pharmacol. 1994; 48: 361-370. doi:10.1016/0006-2952(94)90108-2 (Pubitemid 24243979)
    • (1994) Biochemical Pharmacology , vol.48 , Issue.2 , pp. 361-370
    • Brezden, C.B.1    McClelland, R.A.2    Rauth, A.M.3
  • 101
    • 0028839715 scopus 로고
    • Oxygen dependence of cellular uptake of EF5 [2-(2-nitro-1H-imidazol-1-yl) -N-(2,2,3,3,3-pentafluoropropyl)acetamide]: Analysis of drug adducts by fluorescent antibodies vs bound radioactivity
    • PMid:7547233
    • Koch CJ, Evans SM and Lord EM. Oxygen dependence of cellular uptake of EF5 [2-(2-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide]: Analysis of drug adducts by fluorescent antibodies vs bound radioactivity. Br J Cancer. 1995; 72: 869-874. PMid:7547233
    • (1995) Br J Cancer , vol.72 , pp. 869-874
    • Koch, C.J.1    Evans, S.M.2    Lord, E.M.3
  • 102
    • 0019978257 scopus 로고
    • Oxygen tension, cellular respiration, and redox state as variables influencing the cytotoxicity of the radiosensitizer misonidazole
    • doi:10.2307/3575819
    • Taylor YC and Rauth AM. Oxygen tension, cellular respiration, and redox state as variables influencing the cytotoxicity of the radiosensitizer misonidazole. Radiat Res. 1982; 91: 104-123. doi:10.2307/3575819
    • (1982) Radiat Res , vol.91 , pp. 104-123
    • Taylor, Y.C.1    Rauth, A.M.2
  • 103
    • 0017521276 scopus 로고
    • The use of nitroaromatic compounds as hypoxic cell radiosensitizers
    • PMid:330116
    • Wardman P. The use of nitroaromatic compounds as hypoxic cell radiosensitizers. Curr Top Radiat Res Q. 1977; 11: 347-398. PMid:330116
    • (1977) Curr Top Radiat Res Q , vol.11 , pp. 347-398
    • Wardman, P.1
  • 105
    • 0027522732 scopus 로고
    • Nitroimidazole drugs-action and resistance mechanisms. I. Mechanisms of action
    • doi:10.1093/jac/31.1.9
    • Edwards DI. Nitroimidazole drugs-action and resistance mechanisms. I. Mechanisms of action. J Antimicrob Chemother. 1993; 31: 9-20. doi:10.1093/jac/31.1.9
    • (1993) J Antimicrob Chemother , vol.31 , pp. 9-20
    • Edwards, D.I.1
  • 106
    • 0023937608 scopus 로고
    • Mammalian cell toxicity and bacterial mutagenicity of nitrosoimidazoles
    • DOI 10.1016/0006-2952(88)90252-3
    • Ehlhardt WJ, Beaulieu BB Jr, Goldman P. Mammalian cell toxicity and bacterial mutagenicity of nitrosoimidazoles. Biochem Pharmacol. 1988; 37: 2603-2606. doi:10.1016/0006-2952(88)90252-3 (Pubitemid 18162373)
    • (1988) Biochemical Pharmacology , vol.37 , Issue.13 , pp. 2603-2606
    • Ehlhardt, W.J.1    Beaulieu Jr., B.B.2    Goldman, P.3
  • 107
    • 0017389374 scopus 로고
    • Metronidazole: Review of uses and toxicity
    • doi:10.1093/jac/3.3.205
    • Roe FJ. Metronidazole: review of uses and toxicity. J Antimicrob Chemother. 1977; 3: 205-212. doi:10.1093/jac/3.3.205
    • (1977) J Antimicrob Chemother , vol.3 , pp. 205-212
    • Roe, F.J.1
  • 108
    • 0020575137 scopus 로고
    • Toxicologic evaluation of metronidazole with particular reference to carcinogenic, mutagenic, and teratogenic potential
    • PMid:6336861
    • Roe FJ. Toxicologic evaluation of metronidazole with particular reference to carcinogenic, mutagenic, and teratogenic potential. Surgery. 1983; 93: 158-164. PMid:6336861
    • (1983) Surgery , vol.93 , pp. 158-164
    • Roe, F.J.1
  • 109
    • 0022318319 scopus 로고
    • Safety of nitroimidazoles
    • PMid:3865353
    • Roe FJ. Safety of nitroimidazoles. Scand J Infect Dis Suppl. 1985; 46: 72-81. PMid:3865353
    • (1985) Scand J Infect Dis Suppl , vol.46 , pp. 72-81
    • Roe, F.J.1
  • 110
    • 0019412990 scopus 로고
    • On the mutagenicity of nitroimidazoles
    • PMid:6457989
    • Voogd CE. On the mutagenicity of nitroimidazoles. Mutat Res. 1981; 86: 243-277. PMid:6457989
    • (1981) Mutat Res , vol.86 , pp. 243-277
    • Voogd, C.E.1
  • 111
    • 0002147270 scopus 로고
    • Free radical mechanisms of nitroreductase
    • D. E. Rickert (Ed.). Hemisphere, Washington DC
    • Mason RP, Josephy PP. Free radical mechanisms of nitroreductase. In: D. E. Rickert (Ed.). Toxicity of Nitroaromatic Compounds, Hemisphere, Washington DC, 1985: 121-140.
    • (1985) Toxicity of Nitroaromatic Compounds , pp. 121-140
    • Mason, R.P.1    Josephy, P.P.2
  • 112
    • 0017149955 scopus 로고
    • Antitrichomonad action, mutagenicity, and reduction of metronidazole and other nitroimidazoles
    • PMid:791102
    • Lindmark DG, Muller M. Antitrichomonad action, mutagenicity, and reduction of metronidazole and other nitroimidazoles. Antimicrob Agents Chemother. 1976; 10: 476-482. PMid:791102
    • (1976) Antimicrob Agents Chemother , vol.10 , pp. 476-482
    • Lindmark, D.G.1    Muller, M.2


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