메뉴 건너뛰기




Volumn 52, Issue 5, 2009, Pages 1317-1328

Structure-activity relationships of antitubercular nitroimidazoles. 1. structural features associated with aerobic and anaerobic activities of 4 - And 5-nitroimidazoles

Author keywords

[No Author keywords available]

Indexed keywords

(2 BROMO 4 NITRO 1H IMIDAZOLE 1 YL)BUT 3 EN 2 OL; (TERT BUTYLDIMETHYLSILYLOXY) 3 (2 CHLORO 4 NITRO 1H IMIDAZOL 1 YL)PROPAN 2 OL; 2 (2 METHOXY 4 NITRO 1H IMIDAZOL 1 YL)ETHANOL; 2 (2 METHOXY 6 NITRO 1H IMIDAZOL 1 YL)ETHANOL; 2 BROMO [2 (TERT BUTYLDIMETHYLSILOXY)BUT 3 ENYL] 5 NITRO 1H IMIDAZOLE; 3 (TERT BUTYLDIMETHYLSILYLOXY) 2 (TETRAHYDRO 2H PYRAN 2 YLOXY)PROPYL) 2 CHLORO 5 NITRO 1H IMIDAZOLE; 4 NITROIMIDAZOLE DERIVATIVE; 5 NITROIMIDAZOLE DERIVATIVE; 5,6,7,8 TETRAHYDRO 3 NITROIMIDAZO[1,2 A]PYRIDIN 6 OL; 6 (4 (TRIFLUOROMETHOXY)BENZYLOXY) 5,6 DIHYDRO 2 NITROIMIDAZO[1,2 A]PYRIDINE; 6 (TERT BUTYLDIMETHYLSILYLOXY) 3 NITRO 5,6 DIHYDROIMIDAZO[1,2 A]PYRIDINE; 6 (TERT BUTYLDIMETHYLSILYLOXY) 3 NITRO 5,6,7,8 TETRAHYDROIMIDAZO[1,2 A]PYRIDINE; 6 [4 (TRIFLUOROMETHOXY)BENZYLOXY] 5,6,7,8 TETRAHYDRO 2 NITROIMIDAZO[1,2 A]PYRIDINE; 6 [4 (TRIFLUOROMETHOXY)BENZYLOXY] 6,7 DIHYDRO 3 NITRO 5H IMIDAZO[2,1 B][1,3]OXAZINE; 6,7 DIHYDRO 3 NITRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 OL; 6,7 DIHYDRO 3 NITRO 6 (TETRAHYDRO 2H PYRAN 2 YLOXY) 5H IMIDAZO[2,1 B]OXAZINE; 6,7 DIHYDRO 6 METHOXY 2 NITRO 5H IMIDAZO[2,1 B][1,3]OXAZINE; [2 (4 (TRIFLUOROMETHOXY)BENZYLOXY)BUT 3 ENYL] 4 NITRO 2 VINYL 1H IMIDAZOLE; [2 (4 (TRIFLUOROMETHOXY)BENZYLOXY)ETHYL] 2 METHYL 4 NITRO 1H IMIDAZOLE; [2 (4 (TRIFLUOROMETHOXY)BENZYLOXY)ETHYL] 2 METHYL 5 NITRO 1H IMIDAZOLE; [2 (4 (TRIFLUOROMETHOXY)BENZYLOXY]BUT 3 ENYL] 2 BROMO 4 NITRO 1H IMIDAZOLE; [2 (TERT BUTYLDIMETHYLSILYLOXY)ETHYL] 2 METHOXY 5 NITRO 1H IMIDAZOLE; [2 (TERT BUTYLDIMETHYLSILYOXY)ETHYL] 2 CHLORO 4 NITRO 1H IMIDAZOLE; [2 (TERT BUTYLDIMETHYLSILYOXY)ETHYL] 2 CHLORO 5 NITRO 1H IMIDAZOLE; NITROREDUCTASE; OXAZINE DERIVATIVE; OXYGEN; UNCLASSIFIED DRUG;

EID: 64349089269     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm801246z     Document Type: Article
Times cited : (100)

References (31)
  • 1
    • 84869263771 scopus 로고    scopus 로고
    • WHO International Fact Sheet No
    • WHO International Fact Sheet No. 104, 2007. http://www.who.int/ mediacentre/factsheets/fs104/en/index.html.
    • (2007) , vol.104
  • 2
    • 4644223350 scopus 로고    scopus 로고
    • Prospects for new antitubercular drugs
    • Duncan, K.; Barry, C. E. Prospects for new antitubercular drugs. Curr. Opin. Microbiol. 2004, 7, 460-465.
    • (2004) Curr. Opin. Microbiol , vol.7 , pp. 460-465
    • Duncan, K.1    Barry, C.E.2
  • 3
    • 46249108568 scopus 로고    scopus 로고
    • Via, L. E.; Lin, P. L.; Ray, S. M.; Carrillo, J.; Allen, S. S.; Eum, S. Y.; Taylor, K.; Klein, E.; Manjunatha, U.; Gonzales, J.; Lee, E. G.; Park, S. K.; Raleigh, J. A.; Cho, S. N.; McMurray, D. N.; Flynn, J. L.; Barry, C. E., 3rd. Tuberculous granulomas are hypoxic in guinea pigs, rabbits, and nonhuman primates. Infect Immun. 2008, 76, 2333-40.
    • Via, L. E.; Lin, P. L.; Ray, S. M.; Carrillo, J.; Allen, S. S.; Eum, S. Y.; Taylor, K.; Klein, E.; Manjunatha, U.; Gonzales, J.; Lee, E. G.; Park, S. K.; Raleigh, J. A.; Cho, S. N.; McMurray, D. N.; Flynn, J. L.; Barry, C. E., 3rd. Tuberculous granulomas are hypoxic in guinea pigs, rabbits, and nonhuman primates. Infect Immun. 2008, 76, 2333-40.
  • 4
    • 11144250804 scopus 로고    scopus 로고
    • Tuberculosis. Metabolism and respiration in the absence of growth
    • Boshoff, H. I.; Barry, C. E., 3rd. Tuberculosis. Metabolism and respiration in the absence of growth. Nat. Rev. Microbiol. 2005, 3, 70-80.
    • (2005) Nat. Rev. Microbiol , vol.3 , pp. 70-80
    • Boshoff, H.I.1    Barry 3rd, C.E.2
  • 6
    • 4644371358 scopus 로고    scopus 로고
    • Prospects for clinical introduction of nitroimidazole antibiotics for the treatment of tuberculosis
    • Barry, C. E.; Boshoff, H. I. M.; Dowd, C. S. Prospects for clinical introduction of nitroimidazole antibiotics for the treatment of tuberculosis. Curr. Pharm. Des. 2004, 10, 3239-3262.
    • (2004) Curr. Pharm. Des , vol.10 , pp. 3239-3262
    • Barry, C.E.1    Boshoff, H.I.M.2    Dowd, C.S.3
  • 7
    • 0032526681 scopus 로고    scopus 로고
    • Oxygen depletion induced dormancy in Mycobacterium smegmatis
    • Dick, T.; Lee, B. H.; Murugasu-Oei, B. Oxygen depletion induced dormancy in Mycobacterium smegmatis. FEMS Microbiol. Lett. 1998, 163, 159-164.
    • (1998) FEMS Microbiol. Lett , vol.163 , pp. 159-164
    • Dick, T.1    Lee, B.H.2    Murugasu-Oei, B.3
  • 8
    • 0028024035 scopus 로고
    • Metronidazole is bactericidal to dormant cells of Mycobacterium tuberculosis
    • Wayne, L. G.; Sramek, H. A. Metronidazole is bactericidal to dormant cells of Mycobacterium tuberculosis. Antimicrob. Agents Chemother. 1994, 38, 2054-2058.
    • (1994) Antimicrob. Agents Chemother , vol.38 , pp. 2054-2058
    • Wayne, L.G.1    Sramek, H.A.2
  • 10
    • 0027411717 scopus 로고
    • In vitro and in vivo activities of the nitroimidazole CGI 17341 against Mycobacterium tuberculosis. An - timicrob
    • Ashtekar, D. R.; Costa-Perira, R.; Nagrajan, K.; Vishvanathan, N.; Bhatt, A. D.; Rittel, W. In vitro and in vivo activities of the nitroimidazole CGI 17341 against Mycobacterium tuberculosis. An - timicrob. Agents Chemother. 1993, 37, 183-186.
    • (1993) Agents Chemother , vol.37 , pp. 183-186
    • Ashtekar, D.R.1    Costa-Perira, R.2    Nagrajan, K.3    Vishvanathan, N.4    Bhatt, A.D.5    Rittel, W.6
  • 11
    • 0024819685 scopus 로고
    • Nitroimidazoles XXI 2,3-dihydro-6-nitroimidazo[2,1 - b]oxazoles with antitubercular activity
    • Nagarajan, K.; Shankar, R. G.; Rajappa, S.; Shenoy, S. J.; Costa - Pereira, R. Nitroimidazoles XXI 2,3-dihydro-6-nitroimidazo[2,1 - b]oxazoles with antitubercular activity. Eur. J. Med. Chem. 1989, 24, 631-633.
    • (1989) Eur. J. Med. Chem , vol.24 , pp. 631-633
    • Nagarajan, K.1    Shankar, R.G.2    Rajappa, S.3    Shenoy, S.J.4    Costa - Pereira, R.5
  • 12
    • 53349142215 scopus 로고    scopus 로고
    • Nitroimidazole Antibacterial Compounds and Methods of Use Thereof
    • U.S. Patent 5,668,127
    • Baker, W. R.; Shaopei, C.; Keeler, E. L. Nitroimidazole Antibacterial Compounds and Methods of Use Thereof. U.S. Patent 5,668,127, 1997.
    • (1997)
    • Baker, W.R.1    Shaopei, C.2    Keeler, E.L.3
  • 13
    • 64349119999 scopus 로고    scopus 로고
    • Baker, W. R, Shaopei, C, Keeler, E. L. Nitro-[2,1-b]imidazopyran Compounds and Antibacterial Uses Thereof U.S. Patent 6,087,358,2000
    • Baker, W. R.; Shaopei, C.; Keeler, E. L. Nitro-[2,1-b]imidazopyran Compounds and Antibacterial Uses Thereof U.S. Patent 6,087,358,2000.
  • 14
    • 19544364888 scopus 로고    scopus 로고
    • Lenaerts, A. J.; Gruppo, V.; Marietta, K. S.; Johnson, C. M.; Driscoll, D. K.; Tompkins, N. M.; Rose, J. D.; Reynolds, R. C.; Orme, I. M. Preclinical testing of the nitroimidazopyran PA-824 for activity against Mycobacterium tuberculosis in a series of in vitro and in vivo models. Antimicrob. Agents Chemother. 2005, 49, 2294-2301.
    • Lenaerts, A. J.; Gruppo, V.; Marietta, K. S.; Johnson, C. M.; Driscoll, D. K.; Tompkins, N. M.; Rose, J. D.; Reynolds, R. C.; Orme, I. M. Preclinical testing of the nitroimidazopyran PA-824 for activity against Mycobacterium tuberculosis in a series of in vitro and in vivo models. Antimicrob. Agents Chemother. 2005, 49, 2294-2301.
  • 15
    • 84869263770 scopus 로고    scopus 로고
    • http://www.tballiance.org/home/home.php.
  • 19
    • 0024506946 scopus 로고
    • Synthesis of 1-([18O2]-2-nitro-1 - imidazolyl)-3-methoxy-2-propanol([18O2]-misonidazole)
    • Yang, C.-C.; Goldberg, I. H. Synthesis of 1-([18O2]-2-nitro-1 - imidazolyl)-3-methoxy-2-propanol([18O2]-misonidazole). J. Labelled Compd. Radiopharm. 1989, 27, 423-434.
    • (1989) J. Labelled Compd. Radiopharm , vol.27 , pp. 423-434
    • Yang, C.-C.1    Goldberg, I.H.2
  • 20
    • 0027249805 scopus 로고
    • Solid-liquid phase-transfer catalytic method for N-alkylation of nitroimidazole
    • Liu, Z.-Z.; Chen, H.-C.; Cao, S. L.; Li, R.-T. Solid-liquid phase-transfer catalytic method for N-alkylation of nitroimidazole. Synth. Commun. 1993, 23, 2611-2615.
    • (1993) Synth. Commun , vol.23 , pp. 2611-2615
    • Liu, Z.-Z.1    Chen, H.-C.2    Cao, S.L.3    Li, R.-T.4
  • 21
    • 33644780775 scopus 로고    scopus 로고
    • Synthesis and preliminary evaluation of new 1-and 3-[1-(2-hydroxy-3-phenoxypro - pyl)]xanthines from 2-amino-2-oxazolines as potential A(1)and A(2A)adenosine receptor antagonists
    • Massip, S.; Guillon, J.; Bertarelli, D.; Bosc, J. J.; Leger, J. M.; Lacher, S.; Bontemps, C.; Dupont, T.; Muller, C. E.; Jarry, C. Synthesis and preliminary evaluation of new 1-and 3-[1-(2-hydroxy-3-phenoxypro - pyl)]xanthines from 2-amino-2-oxazolines as potential A(1)and A(2A)adenosine receptor antagonists. Bioorg. Med. Chem. 2006, 14, 2697-2719.
    • (2006) Bioorg. Med. Chem , vol.14 , pp. 2697-2719
    • Massip, S.1    Guillon, J.2    Bertarelli, D.3    Bosc, J.J.4    Leger, J.M.5    Lacher, S.6    Bontemps, C.7    Dupont, T.8    Muller, C.E.9    Jarry, C.10
  • 22
    • 0027249805 scopus 로고
    • Solid-liquid phase-transfer catalytic method for N-alkylation of nitroimidazole
    • Liu, Z.; Chen, H.; Cao, S.; Li, R. Solid-liquid phase-transfer catalytic method for N-alkylation of nitroimidazole. Synth. Commun. 1993, 23, 2611-2615.
    • (1993) Synth. Commun , vol.23 , pp. 2611-2615
    • Liu, Z.1    Chen, H.2    Cao, S.3    Li, R.4
  • 23
    • 8644269592 scopus 로고    scopus 로고
    • A scalable synthesis of a histamine H-3 receptor antagonist
    • Mani, N. S.; Jablonowski, J. A.; Jones, T. K. A scalable synthesis of a histamine H-3 receptor antagonist. J. Org. Chem. 2004, 69, 8115-8117.
    • (2004) J. Org. Chem , vol.69 , pp. 8115-8117
    • Mani, N.S.1    Jablonowski, J.A.2    Jones, T.K.3
  • 24
    • 23044473706 scopus 로고    scopus 로고
    • Synthesis of fused bicyclic imidazoles by sequential van Leusen/ring-closing metathesis reactions
    • Gracias, V.; Gasiecki, A. F.; Djuric, S. W. Synthesis of fused bicyclic imidazoles by sequential van Leusen/ring-closing metathesis reactions. Org. Lett. 2005, 7, 3183-3186.
    • (2005) Org. Lett , vol.7 , pp. 3183-3186
    • Gracias, V.1    Gasiecki, A.F.2    Djuric, S.W.3
  • 25
    • 0042382962 scopus 로고    scopus 로고
    • Synthesis of 8-vinyladenosine 5′-di - and 5′- triphosphate: Evaluation of the diphosphate compound on ribonucleotide reductase
    • Lang, P.; Gerez, C.; Tritsch, D.; Fontecave, M.; Biellmann, J. F.; Burger, A. Synthesis of 8-vinyladenosine 5′-di - and 5′- triphosphate: evaluation of the diphosphate compound on ribonucleotide reductase. Tetrahedron 2003, 59, 7315-7322.
    • (2003) Tetrahedron , vol.59 , pp. 7315-7322
    • Lang, P.1    Gerez, C.2    Tritsch, D.3    Fontecave, M.4    Biellmann, J.F.5    Burger, A.6
  • 26
    • 0001712918 scopus 로고    scopus 로고
    • Cross-metathesis reaction. Generation of highly functionalized olefins from unsaturated alcohols
    • Cossy, J.; BouzBouz, S.; Hoveyda, A. H. Cross-metathesis reaction. Generation of highly functionalized olefins from unsaturated alcohols. J. Organomet. Chem. 2001, 624, 327-332.
    • (2001) J. Organomet. Chem , vol.624 , pp. 327-332
    • Cossy, J.1    BouzBouz, S.2    Hoveyda, A.H.3
  • 27
    • 0037012898 scopus 로고    scopus 로고
    • Wilkinson's catalyst catalyzed selective hydrogenation of olefin in the presence of an aromatic nitro function: A remarkable solvent effect
    • Jourdant, A.; Gonzalez-Zamora, E.; Zhu, J. Wilkinson's catalyst catalyzed selective hydrogenation of olefin in the presence of an aromatic nitro function: a remarkable solvent effect. J. Org. Chem. 2002, 67, 3163-3164.
    • (2002) J. Org. Chem , vol.67 , pp. 3163-3164
    • Jourdant, A.1    Gonzalez-Zamora, E.2    Zhu, J.3
  • 28
    • 84981863391 scopus 로고
    • Nitroimidazoles. 2. Synthesis and reactions of iodonitroimidazoles
    • Hoffer, M.; Toome, V.; Brossi, A. Nitroimidazoles. 2. Synthesis and reactions of iodonitroimidazoles. J. Heterocycl. Chem. 1966, 3, 454-457.
    • (1966) J. Heterocycl. Chem , vol.3 , pp. 454-457
    • Hoffer, M.1    Toome, V.2    Brossi, A.3
  • 29
    • 31044452898 scopus 로고    scopus 로고
    • Manjunatha, U. H.; Boshoff, H.; Dowd, C. S.; Zhang, L.; Albert, T. J.; Norton, J. E.; Daniels, L.; Dick, T.; Pang, S. S.; Barry, C. E., 3rd. Identification of a nitroimidazo-oxazine-specific protein involved in PA-824 resistance in Mycobacterium tuberculosis. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 431-436.
    • Manjunatha, U. H.; Boshoff, H.; Dowd, C. S.; Zhang, L.; Albert, T. J.; Norton, J. E.; Daniels, L.; Dick, T.; Pang, S. S.; Barry, C. E., 3rd. Identification of a nitroimidazo-oxazine-specific protein involved in PA-824 resistance in Mycobacterium tuberculosis. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 431-436.
  • 30
    • 64349122739 scopus 로고    scopus 로고
    • Singh, R.; Manjunatha, U. H.; Boshoff, H.; Ha, Y. H.; Niyomrattanakit, P.; Ledwidge, R.; Dowd, C. S.; Lee, I. Y.; Kim, P.; Zhang, L.; Kang, S.; Keller, T. H.; Jiricek, J.; Barry, C. E., 3rd. Bicyclic nitroimidazoles act as intracellular NO donors and kill non-replicating Mycobacterium tuberculosis. Science, in press.
    • Singh, R.; Manjunatha, U. H.; Boshoff, H.; Ha, Y. H.; Niyomrattanakit, P.; Ledwidge, R.; Dowd, C. S.; Lee, I. Y.; Kim, P.; Zhang, L.; Kang, S.; Keller, T. H.; Jiricek, J.; Barry, C. E., 3rd. Bicyclic nitroimidazoles act as intracellular NO donors and kill non-replicating Mycobacterium tuberculosis. Science, in press.
  • 31
    • 64349121803 scopus 로고    scopus 로고
    • Wayne, L. G. In Mycobacterium Tuberculosis Protocols; Parish, T., Stoker, N. G., Eds.; Humana Press: Totowa, NJ, 2001; pp 247 - 270. JM801246Z
    • Wayne, L. G. In Mycobacterium Tuberculosis Protocols; Parish, T., Stoker, N. G., Eds.; Humana Press: Totowa, NJ, 2001; pp 247 - 270. JM801246Z


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.