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Volumn 79, Issue 4, 2012, Pages 384-397

Synthesis of Novel Nalidixic Acid-Based 1,3,4-Thiadiazole and 1,3,4-Oxadiazole Derivatives as Potent Antibacterial Agents

Author keywords

1; 3; 4 oxadiazole; 4 thiadiazole; Antibacterial activity; Mannich bases; Nalidixic acid

Indexed keywords

1 ETHYL 3 (5 ETHYLSULFANYL 1,3,4 THIADIAZOL 2 YL) 7 METHYL 1H 1,8 NAPHTHYRIDIN 4 ONE; 1 ETHYL 3 (5 MERCAPTO 1,3,4 THIADIAZOL 2 YL) 7 METHYL 1H 1,8 NAPHTHYRIDIN 4 ONE; 1 ETHYL 3 (5 METHANESULFONYL 1,3,4 THIADIAZOL 2 YL) 7 METHYL 1H 1,8 NAPHTHYRIDIN 4 ONE; 1 ETHYL 7 METHYL 3 (5 METHYLSULFANYL 1,3,4 THIADIAZOL 2 YL) 1H 1,8 NAPHTHYRIDIN 4 ONE; 1 ETHYL 7 METHYL 3 (5 PENTYLSULFANYL 1,3,4 THIADIAZOL 2 YL) 1H 1,8 NAPHTHYRIDIN 4 ONE; 1 ETHYL 7 METHYL 3 (5 PROPYLSULFANYL 1,3,4 THIADIAZOL 2 YL) 1H 1,8 NAPHTHYRIDIN 4 ONE; 1 ETHYL 7 METHYL 3 [5 (PROPANE 1 SULFONYL) 1,3,4 THIADIAZOL 2 YL] 1H 1,8 NAPHTHYRIDIN 4 ONE; 1,2,4 THIADIAZOLE DERIVATIVE; 1,3,4 OXADIAZOLE DERIVATIVE; 3 (5 ALLYLSULFANYL 1,3,4 THIADIAZOL 2 YL) 1 ETHYL 7 METHYL 1H 1,8 NAPHTHYRIDIN 4 ONE; 3 (5 BUTYLSULFANYL 1,3,4 THIADIAZOL 2 YL) 1 ETHYL 7 METHYL 1H 1,8 NAPHTHYRIDIN 4 ONE; 3 (5 ETHANESULFONYL 1,3,4 THIADIAZOL 2 YL) 1 ETHYL 7 METHYL 1H 1,8 NAPHTHYRIDIN 4 ONE; 3 [5 (BUTANE 1 SULFONYL) 1,3,4 THIADIAZOL 2 YL] 1 ETHYL 7 METHYL 1H 1,8 NAPHTHYRIDIN 4 ONE; ANTIBIOTIC AGENT; NALIDIXIC ACID; UNCLASSIFIED DRUG;

EID: 84863413020     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2011.01316.x     Document Type: Article
Times cited : (49)

References (41)
  • 2
    • 0023905849 scopus 로고
    • Studies on the interaction of 4-quinolones with DNA by DNA unwinding experiments
    • Tornaletti S., Pedrini A.M. (1988) Studies on the interaction of 4-quinolones with DNA by DNA unwinding experiments. Biochim Biophys Acta;949:279-287.
    • (1988) Biochim Biophys Acta , vol.949 , pp. 279-287
    • Tornaletti, S.1    Pedrini, A.M.2
  • 3
    • 33644944329 scopus 로고    scopus 로고
    • Synthesis and evaluation of new quinazolone derivatives of nalidixic acid as potential antibacterial and antifungal agents
    • Grover G., Kini S.G. (2006) Synthesis and evaluation of new quinazolone derivatives of nalidixic acid as potential antibacterial and antifungal agents. Eur J Med Chem;41:256-262.
    • (2006) Eur J Med Chem , vol.41 , pp. 256-262
    • Grover, G.1    Kini, S.G.2
  • 4
    • 80052929520 scopus 로고    scopus 로고
    • Synthesis, antimicrobial evaluation and QSAR analysis of novel nalidixic acid based 1,2,4-triazole derivatives
    • Aggarwal N., Kumar R., Dureja P., Khurana J.M. (2011) Synthesis, antimicrobial evaluation and QSAR analysis of novel nalidixic acid based 1, 2, 4-triazole derivatives. Eur J Med Chem;46:4089-4099.
    • (2011) Eur J Med Chem , vol.46 , pp. 4089-4099
    • Aggarwal, N.1    Kumar, R.2    Dureja, P.3    Khurana, J.M.4
  • 5
    • 0036176817 scopus 로고    scopus 로고
    • Synthesis and antiinflammatory activity of 1-acylthiosemicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles-3-thiones
    • Palaska E., Sahin G., Kelicen P., Durl N.T. (2002) Synthesis and antiinflammatory activity of 1-acylthiosemicarbazides, 1, 3, 4-oxadiazoles, 1, 3, 4-thiadiazoles and 1, 2, 4-triazoles-3-thiones. Farmaco;57:101-107.
    • (2002) Farmaco , vol.57 , pp. 101-107
    • Palaska, E.1    Sahin, G.2    Kelicen, P.3    Durl, N.T.4
  • 6
    • 0043158794 scopus 로고    scopus 로고
    • Synthesis and anticancer evaluation of some new hydrazone derivatives of 2,6-dimethylimidazo[2,1-b]-[1,3,4]thiadiazole-5-carbohydrazide
    • Terzioglu N., Gursoy A. (2003) Synthesis and anticancer evaluation of some new hydrazone derivatives of 2, 6-dimethylimidazo[2, 1-b]-[1, 3, 4]thiadiazole-5-carbohydrazide. Eur J Med Chem;38:781-786.
    • (2003) Eur J Med Chem , vol.38 , pp. 781-786
    • Terzioglu, N.1    Gursoy, A.2
  • 7
    • 0043158805 scopus 로고    scopus 로고
    • Synthesis characterization and anticancer activity studies on some Mannich bases derived from 1,2,4-triazoles
    • Shivarama Holla B., Veerendra B., Shivanada M.K., Poojary B. (2003) Synthesis characterization and anticancer activity studies on some Mannich bases derived from 1, 2, 4-triazoles. Eur J Med Chem;38:759-765.
    • (2003) Eur J Med Chem , vol.38 , pp. 759-765
    • Shivarama Holla, B.1    Veerendra, B.2    Shivanada, M.K.3    Poojary, B.4
  • 8
    • 0027301137 scopus 로고
    • 1,3,4-Oxadiazole, 1,3,4-thiadiazole, and 1,2,4-triazole analogs of the fenamates: in vitro inhibition of cyclooxygenase and 5-lipoxygenase activities
    • Boschelli D.H., Connor D.T., Bornemeier D.A., Dyer R.D., Kennedy J.A., Kuipers P.J., Okonkwo G.C., Schrier D.J., Wright C.D. (1993) 1, 3, 4-Oxadiazole, 1, 3, 4-thiadiazole, and 1, 2, 4-triazole analogs of the fenamates: in vitro inhibition of cyclooxygenase and 5-lipoxygenase activities. J Med Chem;36:1802-1810.
    • (1993) J Med Chem , vol.36 , pp. 1802-1810
    • Boschelli, D.H.1    Connor, D.T.2    Bornemeier, D.A.3    Dyer, R.D.4    Kennedy, J.A.5    Kuipers, P.J.6    Okonkwo, G.C.7    Schrier, D.J.8    Wright, C.D.9
  • 9
    • 0037396619 scopus 로고    scopus 로고
    • Synthesis and anti-inflammatory activity of 5-(6-methyl-2-substituted 4-pyrimidinyloxymethyl)-1,3,4-oxadiazole-2-thiones and their 3-morpholinomethyl derivatives
    • Jakubkien V., Burbulien M.M., Mekugkien G., Udrnain E., Gaidelis P., Vainilavigius U. (2003) Synthesis and anti-inflammatory activity of 5-(6-methyl-2-substituted 4-pyrimidinyloxymethyl)-1, 3, 4-oxadiazole-2-thiones and their 3-morpholinomethyl derivatives. Farmaco;58:323-328.
    • (2003) Farmaco , vol.58 , pp. 323-328
    • Jakubkien, V.1    Burbulien, M.M.2    Mekugkien, G.3    Udrnain, E.4    Gaidelis, P.5    Vainilavigius, U.6
  • 10
    • 0029802439 scopus 로고    scopus 로고
    • Design, synthesis and antiinflammatory activity of some 1,3,4-oxadiazole derivatives
    • Omar F.A., Mahfouz N.M., Rahman M.A. (1996) Design, synthesis and antiinflammatory activity of some 1, 3, 4-oxadiazole derivatives. Eur J Med Chem;31:819-825.
    • (1996) Eur J Med Chem , vol.31 , pp. 819-825
    • Omar, F.A.1    Mahfouz, N.M.2    Rahman, M.A.3
  • 11
    • 79952410768 scopus 로고    scopus 로고
    • Syntheses of substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole derivatives as potential antimicrobial agent
    • Vosooghi M., Akbarzadeh T., Fallah A., Fazeli M.R., Jamalifar H., Shafiee A. (2005) Syntheses of substituted 1, 3, 4-oxadiazole, 1, 3, 4-thiadiazole and 1, 2, 4-triazole derivatives as potential antimicrobial agent. J Sci I R Iran;16:145-151.
    • (2005) J Sci I R Iran , vol.16 , pp. 145-151
    • Vosooghi, M.1    Akbarzadeh, T.2    Fallah, A.3    Fazeli, M.R.4    Jamalifar, H.5    Shafiee, A.6
  • 12
    • 0027071655 scopus 로고
    • Studies on 2-azetidinone: part vi synthesis and antimicrobial activity of 5-(2′,4′-dichlorophenoxymethyl)-2-(4″-aryl-3″-chloro-2″-azetidinone-1″-yl)-1,3,4-thiadiazole
    • Desai K., Baxi A.J. (1992) Studies on 2-azetidinone: part vi synthesis and antimicrobial activity of 5-(2′, 4′-dichlorophenoxymethyl)-2-(4″-aryl-3″-chloro-2″-azetidinone-1″-yl)-1, 3, 4-thiadiazole. Indian J Pharm Sci;54:183-188.
    • (1992) Indian J Pharm Sci , vol.54 , pp. 183-188
    • Desai, K.1    Baxi, A.J.2
  • 13
    • 0001446322 scopus 로고
    • Synthesis of some thiazolyl-thiosemicarbazides triazoles, oxadiazoles, thiadiazoles & their microbial activity
    • Gawande N.G., Shingare M.S. (1987) Synthesis of some thiazolyl-thiosemicarbazides triazoles, oxadiazoles, thiadiazoles & their microbial activity. Indian J Chem;26B:387-389.
    • (1987) Indian J Chem , vol.26 B , pp. 387-389
    • Gawande, N.G.1    Shingare, M.S.2
  • 14
    • 0029919475 scopus 로고    scopus 로고
    • Synthesis and antimicrobial activity of some 2,5-disubstituted 1,3,4-thiadiazole derivatives
    • Mamolo M.G., Vio L., Banfi E. (1996) Synthesis and antimicrobial activity of some 2, 5-disubstituted 1, 3, 4-thiadiazole derivatives. Farmaco;51:71-74.
    • (1996) Farmaco , vol.51 , pp. 71-74
    • Mamolo, M.G.1    Vio, L.2    Banfi, E.3
  • 15
    • 0021679469 scopus 로고
    • Studies on some thiosemicarbazones and 1,3,4-thiadiazoles as potential antitubercular and antibacterial agents
    • Shucla H.K., Desai N.C., Astik R.R., Thaker K.A. (1984) Studies on some thiosemicarbazones and 1, 3, 4-thiadiazoles as potential antitubercular and antibacterial agents. J Indian Chem Soc;61:168-171.
    • (1984) J Indian Chem Soc , vol.61 , pp. 168-171
    • Shucla, H.K.1    Desai, N.C.2    Astik, R.R.3    Thaker, K.A.4
  • 16
    • 0027221539 scopus 로고
    • Design of 5-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,4-thiadiazoles, -1,3,4-oxadiazoles, and -1,2,4-triazoles as orally active, nonulcerogenic antiinflammatory agents
    • Mullican M.D., Wilson M.W., Connor D.T., Kostlan C.R., Schrier D.J., Dyer R.D. (1993) Design of 5-(3, 5-di-tert-butyl-4-hydroxyphenyl)-1, 3, 4-thiadiazoles, -1, 3, 4-oxadiazoles, and -1, 2, 4-triazoles as orally active, nonulcerogenic antiinflammatory agents. J Med Chem;36:1090-1099.
    • (1993) J Med Chem , vol.36 , pp. 1090-1099
    • Mullican, M.D.1    Wilson, M.W.2    Connor, D.T.3    Kostlan, C.R.4    Schrier, D.J.5    Dyer, R.D.6
  • 17
    • 0033535606 scopus 로고    scopus 로고
    • Synthesis, structure-activity relationships, and in vivo evaluations of substituted di-tert-butylphenols as a novel class of potent, selective, and orally active cyclooxygenase-2 inhibitors. 2. 1,3,4- and 1,2,4-thiadiazole series
    • Song Y., Connor D.T., Sercel A.D., Sorenson R.J., Doubleday R., Unangst P.C., Roth B.D., Beylin V.G., Gilbertsen R.B., Chan K., Schrier D.J., Guglietta A., Bornemeier D.A., Dyer R.D. (1999) Synthesis, structure-activity relationships, and in vivo evaluations of substituted di-tert-butylphenols as a novel class of potent, selective, and orally active cyclooxygenase-2 inhibitors. 2. 1, 3, 4- and 1, 2, 4-thiadiazole series. J Med Chem;42:1161-1169.
    • (1999) J Med Chem , vol.42 , pp. 1161-1169
    • Song, Y.1    Connor, D.T.2    Sercel, A.D.3    Sorenson, R.J.4    Doubleday, R.5    Unangst, P.C.6    Roth, B.D.7    Beylin, V.G.8    Gilbertsen, R.B.9    Chan, K.10    Schrier, D.J.11    Guglietta, A.12    Bornemeier, D.A.13    Dyer, R.D.14
  • 18
    • 0034886444 scopus 로고    scopus 로고
    • Synthesis of 3-(3,4-dimethoxyphenyl)-1H-1,2,4-triazole-5-thiol and 2-amino-5-(3,4-dimethoxy phenyl)-1,3,4-thiadiazole derivatives exhibiting antiinflammatory activity
    • Labanauskas L., Kalcas V., Udrenaite E., Gaidelis P., Brukstus A., Dauksas A. (2001) Synthesis of 3-(3, 4-dimethoxyphenyl)-1H-1, 2, 4-triazole-5-thiol and 2-amino-5-(3, 4-dimethoxy phenyl)-1, 3, 4-thiadiazole derivatives exhibiting antiinflammatory activity. Pharmazie;56:617-619.
    • (2001) Pharmazie , vol.56 , pp. 617-619
    • Labanauskas, L.1    Kalcas, V.2    Udrenaite, E.3    Gaidelis, P.4    Brukstus, A.5    Dauksas, A.6
  • 21
    • 0023895793 scopus 로고
    • Antihypertensive thiadiazoles. 1. Synthesis of some 2-aryl-5-hydrazino-1,3,4-thiadiazoles with vasodilator activity
    • Turner S., Myers M., Gadie B., Nelson A.J., Pape R., Saville J.F., Doxey J.C., Berridge T.L. (1988) Antihypertensive thiadiazoles. 1. Synthesis of some 2-aryl-5-hydrazino-1, 3, 4-thiadiazoles with vasodilator activity. J Med Chem;31:902-906.
    • (1988) J Med Chem , vol.31 , pp. 902-906
    • Turner, S.1    Myers, M.2    Gadie, B.3    Nelson, A.J.4    Pape, R.5    Saville, J.F.6    Doxey, J.C.7    Berridge, T.L.8
  • 23
    • 0027422328 scopus 로고
    • Synthesis and local anesthetic activity of alkylaminoacyl derivatives of 2-amino-1,3,4-thiadiazole
    • Mazzone G., Pignatello R., Mazzone S., Panico A., Penisi G., Castana R., Mazzone P. (1993) Synthesis and local anesthetic activity of alkylaminoacyl derivatives of 2-amino-1, 3, 4-thiadiazole. Farmaco;48:1207-1224.
    • (1993) Farmaco , vol.48 , pp. 1207-1224
    • Mazzone, G.1    Pignatello, R.2    Mazzone, S.3    Panico, A.4    Penisi, G.5    Castana, R.6    Mazzone, P.7
  • 24
    • 0022382279 scopus 로고
    • Antitumour activity 5-substituted 2-acylamino-1,3,4thiadiazole against transplantable rodent tumours
    • Miyamoto K., Koshiura R., Mori M., Yokoi H., Mori C., Hasegawa T., Takatori K. (1985) Antitumour activity 5-substituted 2-acylamino-1, 3, 4thiadiazole against transplantable rodent tumours. Chem Pharm Bull;33:6-5129.
    • (1985) Chem Pharm Bull , vol.33 , pp. 6-5129
    • Miyamoto, K.1    Koshiura, R.2    Mori, M.3    Yokoi, H.4    Mori, C.5    Hasegawa, T.6    Takatori, K.7
  • 25
    • 0038005576 scopus 로고    scopus 로고
    • Investigation of anticancer mechanism of thiadiazole based compound in human nonsmall cell lung cancer A549 cells
    • Chou J.Y., Lai S.Y., Pan S.L., Jow G.M., Chern J.W., Guh J.H. (2003) Investigation of anticancer mechanism of thiadiazole based compound in human nonsmall cell lung cancer A549 cells. Biochem Pharmacol;66:115-124.
    • (2003) Biochem Pharmacol , vol.66 , pp. 115-124
    • Chou, J.Y.1    Lai, S.Y.2    Pan, S.L.3    Jow, G.M.4    Chern, J.W.5    Guh, J.H.6
  • 26
    • 0028866732 scopus 로고
    • Synthesis and pharmacological evaluation of some novel 5-(pyrazol-3-yl)thiadiazole and oxadiazole derivatives as potential hypoglycemic agents
    • Hanna M.A., Girges M.M., Rasala D., Gawinecki R. (1995) Synthesis and pharmacological evaluation of some novel 5-(pyrazol-3-yl)thiadiazole and oxadiazole derivatives as potential hypoglycemic agents. Arzneimittelforschung;45:1074-1078.
    • (1995) Arzneimittelforschung , vol.45 , pp. 1074-1078
    • Hanna, M.A.1    Girges, M.M.2    Rasala, D.3    Gawinecki, R.4
  • 27
    • 0025816212 scopus 로고
    • 2-(Oxadiazolyl)- and 2-(thiazolyl)imidazo[1,2-a]pyrimidines as agonists and inverse agonists at benzodiazepine receptors
    • Tully W.R., Gardner C.R., Gillespie R.J., Westwood R. (1991) 2-(Oxadiazolyl)- and 2-(thiazolyl)imidazo[1, 2-a]pyrimidines as agonists and inverse agonists at benzodiazepine receptors. J Med Chem;34:2060-2067.
    • (1991) J Med Chem , vol.34 , pp. 2060-2067
    • Tully, W.R.1    Gardner, C.R.2    Gillespie, R.J.3    Westwood, R.4
  • 28
    • 0027938648 scopus 로고
    • Improved fischer indole reaction for the preparation of N,N-dimethyltryptamines: synthesis of L-695,894, a potent 5-HT1D receptor agonist
    • Chen C., Senanayake C.H., Bill T.J., Larsen R.D., Veshoeven T.R., Reider P.J. (1994) Improved fischer indole reaction for the preparation of N, N-dimethyltryptamines: synthesis of L-695, 894, a potent 5-HT1D receptor agonist. J Org Chem;59:3738-3741.
    • (1994) J Org Chem , vol.59 , pp. 3738-3741
    • Chen, C.1    Senanayake, C.H.2    Bill, T.J.3    Larsen, R.D.4    Veshoeven, T.R.5    Reider, P.J.6
  • 33
    • 0029046233 scopus 로고
    • Synthesis of 1,2,4-oxadiazole-, 1,3,4-oxadiazole-, and 1,2,4-triazole-derived dipeptidomimetics
    • Borg S., Estenne-Bouhtou G., Luthman K., Csoregh I., Hesselink W., Hacksell U. (1995) Synthesis of 1, 2, 4-oxadiazole-, 1, 3, 4-oxadiazole-, and 1, 2, 4-triazole-derived dipeptidomimetics. J Org Chem;60:3112-3120.
    • (1995) J Org Chem , vol.60 , pp. 3112-3120
    • Borg, S.1    Estenne-Bouhtou, G.2    Luthman, K.3    Csoregh, I.4    Hesselink, W.5    Hacksell, U.6
  • 34
    • 77956043673 scopus 로고    scopus 로고
    • Synthesis and biological activity of novel 2,5-disubstituted-1,3,4-oxadiazoles
    • Shailaja M., Anitha M., Manjula A., Rao B.V. (2010) Synthesis and biological activity of novel 2, 5-disubstituted-1, 3, 4-oxadiazoles. Indian J Chem;49B:1088-1097.
    • (2010) Indian J Chem , vol.49 B , pp. 1088-1097
    • Shailaja, M.1    Anitha, M.2    Manjula, A.3    Rao, B.V.4
  • 36
    • 0002217369 scopus 로고
    • Synthesis and tuberculostatic activity of reaction products 5-(2-,3- and 4-pyridil)-1,3,4-oxadiazol-2-thione with amines
    • Ksepko D.P., Foks H., Janowiec H., Kwiek Z.Z. (1993) Synthesis and tuberculostatic activity of reaction products 5-(2-, 3- and 4-pyridil)-1, 3, 4-oxadiazol-2-thione with amines. Acta Pol Pharm;50:259-267.
    • (1993) Acta Pol Pharm , vol.50 , pp. 259-267
    • Ksepko, D.P.1    Foks, H.2    Janowiec, H.3    Kwiek, Z.Z.4
  • 37
    • 0000312529 scopus 로고
    • 2-Mercapto-5-pyrimidyl-1,3,4-oxadiazole derivatives with a nematocidal and fungicidal activity
    • EP Pat. 371925.
    • Eckhardt W., Beriger E., Zondler H. (1990) 2-Mercapto-5-pyrimidyl-1, 3, 4-oxadiazole derivatives with a nematocidal and fungicidal activity. EP Pat. 371925. Chem Abstr;113:191385.
    • (1990) Chem Abstr , vol.113 , pp. 191385
    • Eckhardt, W.1    Beriger, E.2    Zondler, H.3
  • 38
    • 0018470102 scopus 로고
    • Synthesis and antimycotic activity of 3-methylamino derivatives of various 2-mercapto-5-aryl-1,3,4-oxadiazoles
    • Mazonne G., Bonina F. (1979) Synthesis and antimycotic activity of 3-methylamino derivatives of various 2-mercapto-5-aryl-1, 3, 4-oxadiazoles. Farmaco Sci;34:390-402.
    • (1979) Farmaco Sci , vol.34 , pp. 390-402
    • Mazonne, G.1    Bonina, F.2
  • 39
    • 78650510351 scopus 로고    scopus 로고
    • Synthesis, in vitro antimicrobial and in vivo antitumor evaluation of novel pyrimidoquinolines and its nucleoside derivatives
    • Abbas H.S., Hafez H.N., El-Gazzar A.R.B.A. (2011) Synthesis, in vitro antimicrobial and in vivo antitumor evaluation of novel pyrimidoquinolines and its nucleoside derivatives. Eur J Med Chem;46:21-30.
    • (2011) Eur J Med Chem , vol.46 , pp. 21-30
    • Abbas, H.S.1    Hafez, H.N.2    El-Gazzar, A.R.B.A.3
  • 41
    • 0017250532 scopus 로고
    • Adaptation of membrane lipids to alcohols
    • Ingram L.O. (1976) Adaptation of membrane lipids to alcohols. J Bacteriol;125:670-678.
    • (1976) J Bacteriol , vol.125 , pp. 670-678
    • Ingram, L.O.1


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