메뉴 건너뛰기




Volumn 22, Issue 2, 2013, Pages 768-774

Synthesis and antimicrobial activity of coumarin pyrazole pyrimidine 2,4,6(1H,3H,5H)triones and thioxopyrimidine4,6(1H,5H)diones

Author keywords

Antimicrobial activity; Barbituric acid; Coumarin; Microwave irradiation; Pyrazole; Thiobarbituric acid

Indexed keywords

05 [[3 (6,8 DIBROMO 2 OXO 2H CHROMENE 3 YL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE]DIHYDROTHIOXOPYRIMIDINE 4,6 (1H,5H)DIONE; 5 [[3 (2 OXO 2H BENZO[G]CHROMENE 3 YL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE]PYRIMIDINE 2,4,6 (1H,3H,5H)TRIONE; 5 [[3 (2 OXO 2H CHROMENE 3 YL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE]PYRIMIDINE 2,4,6 (1H,3H,5H)TRIONE; 5 [[3 (6 BROMO 2 OXO 2H CHROMENE 3 YL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE]DIHYDROTHIOXOPYRIMIDINE 4,6 (1H,5H)DIONE; 5 [[3 (6 BROMO2 OXO 2H CHROMENE 3 YL) 1 PHENYL 1H PYRAZOL4YL]METHYLENE]PYRIMIDINE 2,4,6 (1H,3H,5H)TRIONE; 5 [[3 (6 CHLORO 2 OXO 2H CHROMENE 3 YL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE] DIHYDROTHIOXOPYRIMIDINE 4,6 (1H,5H)DIONE; 5 [[3 (6 CHLORO 2 OXO 2H CHROMENE 3 YL) 1 PHENYL 1H PYRAZOL4YL]METHYLENE]PYRIMIDINE 2,4,6 (1H,3H,5H)TRIONE; 5 [[3 (6,8 DIBROMO 2 OXO 2H CHROMENE 3 YL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE]PYRIMIDINE 2,4,6 (1H,3H,5H)TRIONE; 5 [[3 (6,8 DICHLORO 2 OXO 2H CHROMENE 3 YL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE]DIHYDROTHIOXOPYRIMIDINE 4,6 (1H,5H)DIONE; 5 [[3 (6,8 DICHLORO 2 OXO 2H CHROMENE 3 YL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE]PYRIMIDINE 2,4,6 (1H,3H,5H)TRIONE; ACETIC ACID; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; BARBITURIC ACID DERIVATIVE; CIPROFLOXACIN; COUMARIN DERIVATIVE; DIHYDRO 5 [[3 (2 OXO BENZO[G]CHROMENE 3 YL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE]THIOXOPYRIMIDINE 4,6 (1H,5H)DIONE; DIHYDRO 5 [[[3 (2 OXO 2H CHROMENE 3 YL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLENE] 2 THIOXOPYRIMIDINE 4,6 (1H,5H)DIONE; FLUCONAZOLE; THIOBARBITURIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84873996112     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0078-y     Document Type: Article
Times cited : (38)

References (34)
  • 3
    • 0029078472 scopus 로고
    • Microwave assisted organic reactions
    • 10.1016/0040-4020(95)00662-R 1:CAS:528:DyaK2MXot1Wquro%3D
    • Caddick S (1995) Microwave assisted organic reactions. Tetrahedron 51:10403-10432
    • (1995) Tetrahedron , vol.51 , pp. 10403-10432
    • Caddick, S.1
  • 4
    • 0022466602 scopus 로고
    • Synthesis of 3-hetarylcoumarins from 3-acetylcoumarines
    • 10.1016/0143-7208(86)85011-2 1:CAS:528:DyaL28Xks1aiu7o%3D
    • Chodankar NK, Sequeira S, Seshadri S (1986) Synthesis of 3-hetarylcoumarins from 3-acetylcoumarines. Dyes Pigment 7:231-236
    • (1986) Dyes Pigment , vol.7 , pp. 231-236
    • Chodankar, N.K.1    Sequeira, S.2    Seshadri, S.3
  • 5
  • 6
    • 35148824608 scopus 로고    scopus 로고
    • 3,5-Bis(3′-indolyl)pyrazoles, analogues of marine alkaloid nortopsentin: Synthesis and antitumor properties
    • 17911018 10.1016/j.bmcl.2007.09.042 1:CAS:528:DC%2BD2sXhtFOjt77F
    • Diana P, Carbone A, Barraja P, Martorana A, Gia O, DallaVia L, Cirrincione G (2007) 3,5-Bis(3′-indolyl)pyrazoles, analogues of marine alkaloid nortopsentin: synthesis and antitumor properties. Bioorg Med Chem Lett 17:6134-6137
    • (2007) Bioorg Med Chem Lett , vol.17 , pp. 6134-6137
    • Diana, P.1    Carbone, A.2    Barraja, P.3    Martorana, A.4    Gia, O.5    Dallavia, L.6    Cirrincione, G.7
  • 7
    • 0034932118 scopus 로고    scopus 로고
    • Synthesis and biological evalution of several 3-(coumarin-4-yl) tetrahydroisoxazole and 3-(coumarin-4-yl)dihydropyrazole derivatives
    • 10.1002/jhet.5570380329 1:CAS:528:DC%2BD3MXltVSltbk%3D
    • Emmanuel-Giota AA, Fylaktakidou KC, Hadjipavlou-Litina DJ, Litinas KE, Nicolaides DN (2001) Synthesis and biological evalution of several 3-(coumarin-4-yl) tetrahydroisoxazole and 3-(coumarin-4-yl)dihydropyrazole derivatives. J Heterocycl Chem 38:717-722
    • (2001) J Heterocycl Chem , vol.38 , pp. 717-722
    • Emmanuel-Giota, A.A.1    Fylaktakidou, K.C.2    Hadjipavlou-Litina, D.J.3    Litinas, K.E.4    Nicolaides, D.N.5
  • 8
    • 77956436969 scopus 로고
    • BE Patent
    • Esanu A (1985) BE Patent, vol 902, p 232
    • (1985) , vol.902 , pp. 232
    • Esanu, A.1
  • 10
    • 84873994150 scopus 로고    scopus 로고
    • Anti-microbial properties of Scutellaria baicalensis and Coptis chinensis, two traditional Chinese medicines
    • Francesca SL (2011) Anti-microbial properties of Scutellaria baicalensis and Coptis chinensis, two traditional Chinese medicines. Biosc Horiz 1:119-127
    • (2011) Biosc Horiz , vol.1 , pp. 119-127
    • Francesca, S.L.1
  • 11
    • 77956169588 scopus 로고    scopus 로고
    • Synthesis and antimicrobial activity of novel fluorine containing 4-(substituted-2-hydroxybenzoyl)-1H-pyrazoles and pyrazolyl benzo[d]oxazoles
    • 20724151 10.1016/j.bmcl.2010.07.019 1:CAS:528:DC%2BC3cXhtV2jt7jM
    • Gadakh AV, Pandit C, Rindhe SS, Karale BK (2010) Synthesis and antimicrobial activity of novel fluorine containing 4-(substituted-2- hydroxybenzoyl)-1H-pyrazoles and pyrazolyl benzo[d]oxazoles. Bioorg Med Chem Lett 20:5572-5576
    • (2010) Bioorg Med Chem Lett , vol.20 , pp. 5572-5576
    • Gadakh, A.V.1    Pandit, C.2    Rindhe, S.S.3    Karale, B.K.4
  • 12
    • 0034649564 scopus 로고    scopus 로고
    • Inhibition of monoamine oxidases by functionalized coumarin derivatives: Biological activities, QSARs, and 3D-QSARs
    • 11123983 10.1021/jm001028o 1:CAS:528:DC%2BD3cXnvFarsbY%3D
    • Gnerre C, Catto M, Leonetti F, Weber P, Carrupt P-A, Altomare C, Carotti A, Testa B (2000) Inhibition of monoamine oxidases by functionalized coumarin derivatives: biological activities, QSARs, and 3D-QSARs. J Med Chem 43:4747-4758
    • (2000) J Med Chem , vol.43 , pp. 4747-4758
    • Gnerre, C.1    Catto, M.2    Leonetti, F.3    Weber, P.4    Carrupt, P.-A.5    Altomare, C.6    Carotti, A.7    Testa, B.8
  • 13
    • 79953776648 scopus 로고    scopus 로고
    • Coumarin-purine ribofuranoside conjugates as new agents against hepatitis C virus
    • 10.1021/jm101337v
    • Jih Ru, Hwu S-YL, Tsay S-C, De Clercq E, Leyssen P, Neyts J (2011) Coumarin-purine ribofuranoside conjugates as new agents against hepatitis C virus. J Med Chem 54:2114-2126
    • (2011) J Med Chem , vol.54 , pp. 2114-2126
    • Jih, R.1    Hwu, S.-Y.2    Tsay, S.-C.3    De Clercq, E.4    Leyssen, P.5    Neyts, J.6
  • 17
    • 0029063981 scopus 로고
    • Synthesis,toxicological and pharmacological assessment of some 4-hydroxycoumarin
    • 10.1016/0223-5234(96)88266-3 1:CAS:528:DyaK2MXntVClsr8%3D
    • Manolov I, Danchev ND (1995) Synthesis,toxicological and pharmacological assessment of some 4-hydroxycoumarin. Eur J Med Chem 30:531-536
    • (1995) Eur J Med Chem , vol.30 , pp. 531-536
    • Manolov, I.1    Danchev, N.D.2
  • 18
    • 33847301366 scopus 로고    scopus 로고
    • Barbituric acid activation and modulation of GABA receptors in neocortex
    • 17289092 10.1016/j.neuropharm.2006.12.004 1:CAS:528:DC%2BD2sXitl2ltLc%3D
    • Mathers DA, Wan X (2007) Barbituric acid activation and modulation of GABA receptors in neocortex. Neuropharmacology 52:1160-1168
    • (2007) Neuropharmacology , vol.52 , pp. 1160-1168
    • Mathers, D.A.1    Wan, X.2
  • 19
    • 2342474593 scopus 로고    scopus 로고
    • Microwave-assisted chemistry in drug discovery
    • 1:CAS:528:DC%2BD2cXjtVeisrg%3D
    • Mavandadi FM, Lidström P (2004) Microwave-assisted chemistry in drug discovery. Curr Topics Drug Discov 4:773-792
    • (2004) Curr Topics Drug Discov , vol.4 , pp. 773-792
    • Mavandadi, F.M.1    Lidström, P.2
  • 21
    • 70349774252 scopus 로고    scopus 로고
    • Synthesis, antimicrobial and antioxidant activities of substituted pyrazoles, isoxazoles, pyrimidine and thioxopyrimidine derivatives
    • 19631423 10.1016/j.ejmech.2009.06.024 1:CAS:528:DC%2BD1MXht1GgtbrF
    • Padmaja A, Payani T, Dinneswara RG, Padmavathi V (2009) Synthesis, antimicrobial and antioxidant activities of substituted pyrazoles, isoxazoles, pyrimidine and thioxopyrimidine derivatives. Eur J Med Chem 44:4557-4566
    • (2009) Eur J Med Chem , vol.44 , pp. 4557-4566
    • Padmaja, A.1    Payani, T.2    Dinneswara, R.G.3    Padmavathi, V.4
  • 22
    • 80053198391 scopus 로고    scopus 로고
    • Synthesis and antioxidant activity of oxazolyl/thiazolylsulfonylmethyl pyrazoles and isoxazoles
    • 21864949 10.1016/j.ejmech.2011.08.010 1:CAS:528:DC%2BC3MXht1amt7rE
    • Padmaja A, Rajasekhar C, Muralikrishna A, Padmavathi V (2011) Synthesis and antioxidant activity of oxazolyl/thiazolylsulfonylmethyl pyrazoles and isoxazoles. Eur J Med Chem 46:5034-5038
    • (2011) Eur J Med Chem , vol.46 , pp. 5034-5038
    • Padmaja, A.1    Rajasekhar, C.2    Muralikrishna, A.3    Padmavathi, V.4
  • 24
    • 0036750293 scopus 로고    scopus 로고
    • Facile synthesis of [1]benzopyrano[4,3-c] pyrazoles, 1- aryl-3- (2formamidophenyl)pyrazoles and 1-aryl-3-phenyl-4-alkylpyrazoles using vilsmeier reagent
    • 1:CAS:528:DC%2BD38Xns1Oisrc%3D
    • Selvi S, Perumal PT (2002a) Facile synthesis of [1]benzopyrano[4,3-c] pyrazoles, 1- aryl-3- (2formamidophenyl)pyrazoles and 1-aryl-3-phenyl-4- alkylpyrazoles using vilsmeier reagent. Indian J Chem 41B:1887-1893
    • (2002) Indian J Chem , vol.41 , pp. 1887-1893
    • Selvi, S.1    Perumal, P.T.2
  • 25
    • 0036875228 scopus 로고    scopus 로고
    • A short, facile method for the synthesis of 1-aryl-3-phenyl-4- alkylpyrazoles using microwave irradiation
    • 10.1002/jhet.5570390603 1:CAS:528:DC%2BD3sXmtFOnsg%3D%3D
    • Selvi S, Perumal PT (2002b) A short, facile method for the synthesis of 1-aryl-3-phenyl-4-alkylpyrazoles using microwave irradiation. J Heterocycl Chem 39:1129-1131
    • (2002) J Heterocycl Chem , vol.39 , pp. 1129-1131
    • Selvi, S.1    Perumal, P.T.2
  • 26
    • 65149100170 scopus 로고    scopus 로고
    • Design, synthesis and anticancer activities of hybrids of indole and barbituric acids identification of highly promising leads
    • 19398334 10.1016/j.bmcl.2009.04.014 1:CAS:528:DC%2BD1MXmtVers7w%3D
    • Singh P, Kaur M, Verma P (2009) Design, synthesis and anticancer activities of hybrids of indole and barbituric acids identification of highly promising leads. Bioorg Med Chem Lett 19:3054-3058
    • (2009) Bioorg Med Chem Lett , vol.19 , pp. 3054-3058
    • Singh, P.1    Kaur, M.2    Verma, P.3
  • 27
    • 62949193424 scopus 로고    scopus 로고
    • A study of the antimicrobial activity of selected naturally occurring and synthetic coumarins
    • 19155158 10.1016/j.ijantimicag.2008.10.022 1:CAS:528:DC%2BD1MXjvVWqtro%3D
    • Smyth T, Ramachandran VN, Smyth WF (2009) A study of the antimicrobial activity of selected naturally occurring and synthetic coumarins. Int J Antimicrob Agents 33:421-426
    • (2009) Int J Antimicrob Agents , vol.33 , pp. 421-426
    • Smyth, T.1    Ramachandran, V.N.2    Smyth, W.F.3
  • 28
    • 51349147434 scopus 로고    scopus 로고
    • New PPARγ ligands based on barbituric acid: Virtual screening, synthesis and receptor binding studies
    • 18752947 10.1016/j.bmcl.2008.08.028 1:CAS:528:DC%2BD1cXhtFelsr3I
    • Sundriyal S, Viswanad B, Poduri R, Chakraborti AK, Bharatam PV (2008) New PPARγ ligands based on barbituric acid: virtual screening, synthesis and receptor binding studies. Bioorg Med Chem Lett 18:4959-4962
    • (2008) Bioorg Med Chem Lett , vol.18 , pp. 4959-4962
    • Sundriyal, S.1    Viswanad, B.2    Poduri, R.3    Chakraborti, A.K.4    Bharatam, P.V.5
  • 29
    • 78650516574 scopus 로고    scopus 로고
    • 3-[Benzimidazo- and 3-[benzothiadiazoleimidazo-(1,2-c)quinazolin-5-yl]- 2H-chromene-2-ones as potent antimicrobial agents
    • 10.1016/j.bmcl.2010.10.082
    • Suresh Kuarm B, Thirupathi Reddy Y, Venu Madhav J, Crooks PA, Rajitha B (2011) 3-[Benzimidazo- and 3-[benzothiadiazoleimidazo-(1,2-c)quinazolin-5-yl]- 2H-chromene-2-ones as potent antimicrobial agents. Bio Org Med Chem Lett 21:524-527
    • (2011) Bio Org Med Chem Lett , vol.21 , pp. 524-527
    • Suresh Kuarm, B.1    Thirupathi Reddy, Y.2    Venu Madhav, J.3    Crooks, P.A.4    Rajitha, B.5
  • 30
    • 72249098975 scopus 로고    scopus 로고
    • Novel substituted (Z)-5-((N-benzyl-1H-indol-3-yl) methylene) imidazolidine-2,4-diones and 5-((N-benzyl-1H-indol-3-yl)methylene) pyrimidine-2,4,6(1H,3H,5H)-triones as potent radio-sensitizing agents
    • 10.1016/j.bmcl.2009.11.082
    • Thirupathi Reddy Y, Konjeti R, Sekhar, Nidhish Sasi, Narsimha Reddy P, Michael L, Freeman, Crooks PA (2010) Novel substituted (Z)-5-((N-benzyl-1H- indol-3-yl) methylene)imidazolidine-2,4-diones and 5-((N-benzyl-1H-indol-3-yl) methylene) pyrimidine-2,4,6(1H,3H,5H)-triones as potent radio-sensitizing agents. Bioo. Bioorg Med Chem Lett 20:600-602
    • (2010) Bioo. Bioorg Med Chem Lett , vol.20 , pp. 600-602
    • Thirupathi Reddy, Y.1    Konjeti, R.2    Sekhar3    Nidhish, S.4    Narsimha Reddy, P.5    Michael, L.6    Freeman7    Crooks, P.A.8
  • 31
    • 0033444261 scopus 로고    scopus 로고
    • Solvent-free organic syntheses using supported reagents and microwave Irradiation
    • 10.1039/a808223e
    • Verma RS (1999) Solvent-free organic syntheses using supported reagents and microwave Irradiation. Green Chem 1:43-55
    • (1999) Green Chem , vol.1 , pp. 43-55
    • Verma, R.S.1
  • 32
  • 34
    • 67651172776 scopus 로고    scopus 로고
    • Inhibitory effects of 5-benzylidene barbiturate derivatives on mushroom tyrosinase and their antibacterial activities
    • 19552984 10.1016/j.ejmech.2009.05.023 1:CAS:528:DC%2BD1MXptlertb8%3D
    • Yan Q, Cao R, Yi W, Chen Z, Wen H, Ma L, Song H (2009) Inhibitory effects of 5-benzylidene barbiturate derivatives on mushroom tyrosinase and their antibacterial activities. Eur J Med Chem 44:4235-4243
    • (2009) Eur J Med Chem , vol.44 , pp. 4235-4243
    • Yan, Q.1    Cao, R.2    Yi, W.3    Chen, Z.4    Wen, H.5    Ma, L.6    Song, H.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.