메뉴 건너뛰기




Volumn 21, Issue 6, 2012, Pages 788-795

QSAR studies on substituted 3- or 4-phenyl-1,8-naphthyridine derivatives as antimicrobial agents

Author keywords

Antibacterial and molecular descriptors; Antitubercular; Genetic function approximation; Quantitative structure activity relationship

Indexed keywords

3 PHENYL 1,8 NAPHTHYRIDINE DERIVATIVE; 4 PHENYL 1,8 NAPHTHYRIDINE DERIVATIVE; ANTIINFECTIVE AGENT; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

EID: 84861867819     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9564-x     Document Type: Article
Times cited : (10)

References (34)
  • 2
    • 0037205951 scopus 로고    scopus 로고
    • Synthesis of variously substituted 1,8-naphthyridine derivatives and evaluation of their antimycobacterial activity
    • DOI 10.1016/S0014-827X(02)01235-1, PII S0014827X02012351
    • Badawneh M, Manera C, Mori C, Saccomanni G, Ferrarini PL (2002) Synthesis of variously substituted 1,8-naphthyridine derivatives and evaluation of their antimycobacterial activity. Il Farmaco 57:631-639 (Pubitemid 34876989)
    • (2002) Farmaco , vol.57 , Issue.8 , pp. 631-639
    • Badawneh, M.1    Manera, C.2    Mori, C.3    Saccomanni, G.4    Ferrarini, P.L.5
  • 3
    • 0141788046 scopus 로고    scopus 로고
    • Synthesis of 3- or 4-phenyl-1,8-naphthyridine derivatives and evaluation of antimycobacterial and antimicrobial activity
    • DOI 10.1016/S0014-827X(03)00144-7
    • Badawneh M, Bellini L, Cavallini T, Jamal JA, Manera C, Saccomanni G, Ferrarini PL (2003) Synthesis of 3- or 4-phenyl-1,8-naphthyridine derivatives and evaluation of antimycobacterial and antimicrobial activity. Il Farmaco 58:859-866 (Pubitemid 37122658)
    • (2003) Farmaco , vol.58 , Issue.9 , pp. 859-866
    • Badawneh, M.1    Bellini, L.2    Cavallini, T.3    Al Jamal, J.4    Manera, C.5    Saccomanni, G.6    Ferrarini, P.L.7
  • 4
    • 0026507066 scopus 로고
    • Fluoronaphthyridines as antibacterial agents. 4. Synthesis and structure-activity relationships of 5-substituted-6-fluoro-7-(cycloalkylamino)- 1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids
    • Bouzard D, DiCesare PP, Essiz M, Jacquet JP, Ledoussal B, Remuzon P, Kessler RE, Fung TJ (1992) Fluoronaphthyridines as antibacterial agents. 4. Synthesis and structure-activity relationships of 5-substituted-6-fluoro-7- (cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids. J Med Chem 35: 518-525
    • (1992) J Med Chem , vol.35 , pp. 518-525
    • Bouzard, D.1    Dicesare, P.P.2    Essiz, M.3    Jacquet, J.P.4    Ledoussal, B.5    Remuzon, P.6    Kessler, R.E.7    Fung, T.J.8
  • 7
    • 0034897586 scopus 로고    scopus 로고
    • Synthesis and QSAR studies of 4-substituted phenyl-2,6-dimethyl-3, 5-bis-N-(substituted phenyl)carbamoyl-1,4-dihydropyridines as potential antitubercular agents
    • DOI 10.1016/S0968-0896(01)00141-9, PII S0968089601001419
    • Desai B, Sureja D, Naliapara Y, Shaha A, Saxena AK (2001) Synthesis and QSAR Studies of 4-Substituted phenyl-2,6-dimethyl-3,5-bis-N-(substituted phenyl)carbamoyl-1,4-dihydropyridines as potential antitubercular agents. Bioorg Med Chem 9:1993-1998 (Pubitemid 32739187)
    • (2001) Bioorganic and Medicinal Chemistry , vol.9 , Issue.8 , pp. 1993-1998
    • Desai, B.1    Sureja, D.2    Naliapara, Y.3    Shah, A.4    Saxena, A.K.5
  • 8
    • 58049169788 scopus 로고    scopus 로고
    • Antitubercular activities of novel benzothiazolo naphthyridone carboxylic acid derivatives endowed with high activity toward multi-drug resistant tuberculosis
    • Dinakaran M, Senthilkumar P, Yogeeswari P, Sriram D (2009) Antitubercular activities of novel benzothiazolo naphthyridone carboxylic acid derivatives endowed with high activity toward multi-drug resistant tuberculosis. Biomed Pharmcother 63:11-18
    • (2009) Biomed Pharmcother , vol.63 , pp. 11-18
    • Dinakaran, M.1    Senthilkumar, P.2    Yogeeswari, P.3    Sriram, D.4
  • 9
    • 0032583464 scopus 로고    scopus 로고
    • Synthesis and evaluation of antimycobacterial activity of 4-phenyl-1,8-naphthyridine derivatives
    • DOI 10.1016/S0014-827X(98)00094-9, PII S0014827X98000949
    • Ferrarini PL, Manera C, Mori C, Badawneh M, Saccomannim G (1998) Synthesis and evaluation of antimycobacterial activity of 4-phenyl-1,8- naphthyridine derivatives. Il Farmaco 53:741-746 (Pubitemid 29171486)
    • (1998) Farmaco , vol.53 , Issue.12 , pp. 741-746
    • Luigi Ferrarini, P.1    Manera, C.2    Mori, C.3    Badawneh, M.4    Saccomanni, G.5
  • 10
    • 0034706933 scopus 로고    scopus 로고
    • Synthesis and antiplatelet activity of some 3-phenyl-1,8-naphthyridine derivatives
    • DOI 10.1016/S0014-827X(00)00085-9, PII S0014827X00000859
    • Ferrarini PL, Mori C, Badawneh M, Franconi F, Manera C, Miceli M, Saccomanni G (2000) Synthesis and antiplatelet activity of some 3-phenyl-1,8-naphthyridine derivatives. Il Farmaco 55:603-610 (Pubitemid 32007911)
    • (2000) Farmaco , vol.55 , Issue.9-10 , pp. 603-610
    • Ferrarini, P.L.1    Mori, C.2    Badawneh, M.3    Franconi, F.4    Manera, C.5    Miceli, M.6    Saccomanni, G.7
  • 11
    • 0035305750 scopus 로고    scopus 로고
    • Synthesis and antiplatelet activity of some 2,7-di(N-cycloamino)-3- phenyl-1,8-naphthyridine derivatives
    • DOI 10.1016/S0014-827X(01)01075-8, PII S0014827X01010758
    • Ferrarini PL, Badawneh M, Franconi F, Manera C, Miceli M, Mori C, Saccomanni G (2001) Synthesis and antiplatelet activity of some 2,7-di(N-cycloamino)-3-phenyl-1,8-naphthyridine derivatives. Il Farmaco 56:311-318 (Pubitemid 32463315)
    • (2001) Farmaco , vol.56 , Issue.4 , pp. 311-318
    • Ferrarini, P.L.1    Badawneh, M.2    Franconi, F.3    Manera, C.4    Miceli, M.5    Mori, C.6    Saccomanni, G.7
  • 12
    • 40749117261 scopus 로고    scopus 로고
    • Synthesis, antituberculosis activity and QSAR study of some novel 2-(nitroaryl)-5-(nitrobenzylsulfinyl and sulfonyl)-1,3,4-thiadiazole derivatives
    • Foroumadi A, Sakhteman A, Sharifzadeh Z, Mohammadhosseini N, Hemmateenejad B, Moshafi MH, Vosooghi M, Amini M, Shafiee A (2007) Synthesis, antituberculosis activity and QSAR study of some novel 2-(nitroaryl)-5- (nitrobenzylsulfinyl and sulfonyl)-1,3,4-thiadiazole derivatives. DARU 15(4):218-226 (Pubitemid 351377887)
    • (2007) Daru , vol.15 , Issue.4 , pp. 218-226
    • Foroumadi, A.1    Sakhteman, A.2    Sharifzadeh, Z.3    Mohammadhosseini, N.4    Hemmateenejad, B.5    Moshafi, M.H.6    Vosooghi, M.7    Amini, M.8    Shafiee, A.9
  • 13
    • 84988109729 scopus 로고
    • Atomic physicochemical parameters for three-dimensional structure-directed quantitative structureactivity relationships I. Partition coefficients as a measure of hydrophobicity
    • Ghose AK, Crippen GM (1986) Atomic physicochemical parameters for three-dimensional structure-directed quantitative structureactivity relationships I. Partition coefficients as a measure of hydrophobicity. J Comput Chem 7:565-577
    • (1986) J Comput Chem , vol.7 , pp. 565-577
    • Ghose, A.K.1    Crippen, G.M.2
  • 14
    • 0000381930 scopus 로고    scopus 로고
    • Prediction of hydrophobic (lipophilic) properties of small organic molecules using fragmental methods: An analysis of ALOGP and CLOGP methods
    • Ghose AK, Viswanadhan VN, Wendoloski JJ (1998) Prediction of hydrophobic (lipophilic) properties of small organic molecules using fragmental methods: an analysis of ALOGP and CLOGP methods. J Phys Chem A 102:3762-3772 (Pubitemid 128611348)
    • (1998) Journal of Physical Chemistry A , vol.102 , Issue.21 , pp. 3762-3772
    • Ghose, A.K.1    Viswanadhan, V.N.2    Wendoloski, J.J.3
  • 18
    • 0035169586 scopus 로고    scopus 로고
    • Three-dimensional quantitative structure - Activity relationship (3D-QSAR) of 3-aryloxazolidin-2-one antibacterials
    • DOI 10.1016/S0968-0896(01)00186-9, PII S0968089601001869
    • Karki RG, Kulkarni VM (2001) Three-dimensional quantitative structure-activity relationship (3D-QSAR) of 3-aryloxazolidin-2-one antibacterials. Biorg Med Chem 9:3153-3160 (Pubitemid 33065615)
    • (2001) Bioorganic and Medicinal Chemistry , vol.9 , Issue.12 , pp. 3153-3160
    • Karki, R.G.1    Kulkarni, V.M.2
  • 20
    • 0026533179 scopus 로고
    • A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides
    • Kuroda T, Suzuki F, Tamura T, Ohmori K, Hosoe H (1992) A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8- naphthyridine-3-carboxamides. J Med Chem 35:1130-1136
    • (1992) J Med Chem , vol.35 , pp. 1130-1136
    • Kuroda, T.1    Suzuki, F.2    Tamura, T.3    Ohmori, K.4    Hosoe, H.5
  • 21
    • 0026748614 scopus 로고
    • Antibacterial activity of a 1, 8-naphthyridine quinolone, PD 13 1628
    • Lewin CS (1992) Antibacterial activity of a 1, 8-naphthyridine quinolone, PD 13 1628. J Med Microbiol 36:353-357
    • (1992) J Med Microbiol , vol.36 , pp. 353-357
    • Lewin, C.S.1
  • 22
    • 22544449537 scopus 로고    scopus 로고
    • Recent advances in new structural classes of anti-tuberculosis agents
    • DOI 10.2174/0929867054546654
    • Nayyar A, Jain R (2005) Recent advances in new structural classes of anti-tuberculosis agents. Curr Med Chem 12:1873-1886 (Pubitemid 41015184)
    • (2005) Current Medicinal Chemistry , vol.12 , Issue.16 , pp. 1873-1886
    • Nayyar, A.1    Jain, R.2
  • 23
    • 2742585890 scopus 로고    scopus 로고
    • Synthesis and antimicrobial activity of 1', 2', 4'-triazolyl/1', 3', 4'-thiadiazolyl/1', 3', 4'-oxadiazolyl-1, 8-naphthyridines and related compounds
    • Rao GR, Mogilaiah K, Sreenivasulu B (1996) Synthesis and antimicrobial activity of 1′, 2′, 4′-triazolyl/1′, 3′, 4′-thiadiozolyl/1′, 3′, 4′-oxadiazolyl-1,8- naphthyridines and related compounds. Indian J Chem 35B:339-344 (Pubitemid 126462150)
    • (1996) Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry , vol.35 , Issue.4 , pp. 339-344
    • Rama Rao, G.1    Mogilaiah, K.2    Sreenivasulu, B.3
  • 24
    • 0028467707 scopus 로고
    • Application of genetic function approximation to quantitative structure-activity relationships and quantitative structure-property relationships
    • Rogers D, Hopfinger AJ (1994) Application of genetic function approximation to quantitative structure-activity relationships and quantitative structure-property relationships. J Chem Inf Comput Sci 34:854-866
    • (1994) J Chem Inf Comput Sci , vol.34 , pp. 854-866
    • Rogers, D.1    Hopfinger, A.J.2
  • 25
    • 0023627689 scopus 로고
    • 2-Oxo-1,8-naphthyridine-3-carboxylic acid derivatives with potent gastric antisecretory properties
    • DOI 10.1021/jm00395a015
    • Santilli A, Scotese AC, Bauer RF, Bell SC (1987) 2-Oxo-1,8-naphthyridine- 3-carboxylic acid derivatives with potent gastric antisecretory properties. J Med Chem 30:2270-2277 (Pubitemid 17167475)
    • (1987) Journal of Medicinal Chemistry , vol.30 , Issue.12 , pp. 2270-2277
    • Santilli, A.A.1    Scotese, A.C.2    Bauer, R.F.3    Bell, S.C.4
  • 26
    • 34250801083 scopus 로고    scopus 로고
    • CoMFA and CoMSIA 3D-QSAR analysis of diaryloxy-methano-phenanthrene derivatives as anti-tubercular agents
    • DOI 10.1007/s00894-006-0124-0
    • Shagufta KumarA, Panda G, Siddiqi MI (2007) CoMFA and CoMSIA 3D-QSAR analysis of diaryloxy-methano-phenanthrene derivatives as anti-tubercular agents. J Mol Model 13:99-109 (Pubitemid 44823957)
    • (2007) Journal of Molecular Modeling , vol.13 , Issue.1 , pp. 99-109
    • Shagufta1    Kumar, A.2    Panda, G.3    Siddiqi, M.I.4
  • 27
    • 33846069819 scopus 로고    scopus 로고
    • QSAR studies on chalcones and flavonoids as antituberculosis agents using genetic function approximation (GFA) method
    • Sivakumar PM, Geetha Babu SK, Doble M (2007a) QSAR studies on chalcones and flavonoids as antituberculosis agents using genetic function approximation (GFA) method. Chem Pharm Bull 55: 44-50
    • (2007) Chem Pharm Bull , vol.55 , pp. 44-50
    • Sivakumar, P.M.1    Geetha Babu, S.K.2    Doble, M.3
  • 28
    • 33847255838 scopus 로고    scopus 로고
    • Synthesis, antimycobacterial activity evaluation, and QSAR studies of chalcone derivatives
    • Sivakumar PM, Seenivasan SP, Kumar V, DobleM(2007b) Synthesis, antimycobacterial activity evaluation, and QSAR studies of chalcone derivatives. Bioorg Med Chem Lett 17:1695-1700
    • (2007) Bioorg Med Chem Lett , vol.17 , pp. 1695-1700
    • Sivakumar, P.M.1    Seenivasan, S.P.2    Doblem, K.V.3
  • 29
    • 42049108913 scopus 로고    scopus 로고
    • Impact of topological and electronic descriptors in the QSAR of pyrazine containing thiazolines and thiazolidinones as antitubercular and antibacterial agents
    • DOI 10.1111/j.1747-0285.2008.00657.x
    • Sivakumar PM, Geetha Babu SK, Doble M (2008) Impact of topological and eElectronic descriptors in the QSAR of pyrazine containing thiazolines and thiazolidinones as antitubercular and antibacterial agents. Chem Biol Drug Des 71:447-463 (Pubitemid 351519507)
    • (2008) Chemical Biology and Drug Design , vol.71 , Issue.5 , pp. 447-463
    • Sivakumar, P.M.1    Geetha Babu, S.K.2    Doble, M.3
  • 31
    • 84984376233 scopus 로고
    • New molecular descriptors for 2D- and 3D-structures
    • Todeschini R, Lasagni M, Marengo E (1994) New molecular descriptors for 2D- and 3D-structures. J Chemom 8:263-273
    • (1994) J Chemom , vol.8 , pp. 263-273
    • Todeschini, R.1    Lasagni, M.2    Marengo, E.3
  • 32
    • 0024716284 scopus 로고
    • Atomic physicochemical parameters for three dimensional structure directed quantitative structure-activity relationships. 4. Additional parameters for hydrophobic and dispersive interactions and their application for an automated superposition of certain naturally occurring nucleoside antibiotics
    • Viswanadhan VN, Ghose AK, Reyankar GR, Robins RK (1989) Atomic physicochemical parameters for three dimensional structure directed quantitative structure-activity relationships. 4. Additional parameters for hydrophobic and dispersive interactions and their application for an automated superposition of certain naturally occurring nucleoside antibiotics. J Chem Inf Comput Sci 29:163-172
    • (1989) J Chem Inf Comput Sci , vol.29 , pp. 163-172
    • Viswanadhan, V.N.1    Ghose, A.K.2    Reyankar, G.R.3    Robins, R.K.4
  • 33
    • 0032520840 scopus 로고    scopus 로고
    • Molecular mechanisms of polymyxin β-membrane interactions: Direct correlation between surface charge density and self-promoted transport
    • DOI 10.1007/s002329900350
    • Wiese A, Munstermann M, Gutsmann T, Lindner B, Kawahara K, Zahringer U, Seydel U (1998) Molecular mechanisms of polymyxin B-membrane interactions: direct correlation between surface charge density and self-promoted transport. J Membrane Biol 162:127-138 (Pubitemid 28143155)
    • (1998) Journal of Membrane Biology , vol.162 , Issue.2 , pp. 127-138
    • Wiese, A.1    Munstermann, M.2    Gutsmann, T.3    Lindner, B.4    Kawahara, K.5    Zahringer, U.6    Seydel, U.7
  • 34
    • 0033533865 scopus 로고    scopus 로고
    • Antitumor agents. 196. Substituted 2-thienyl-1,8-naphthyridin-4-ones: Their synthesis, cytotoxicity, and inhibition of tubulin polymerization
    • DOI 10.1021/jm990208z
    • Zhang SX, Bastow KF, Tachibana Y, Kuo SC, Hamel E, Mauger A, Narayanan VL, Lee KH (1999) Antitumor agents. 196. Substituted 2-thienyl-1,8-naphthyridin- 4-ones: their synthesis, cytotoxicity, and inhibition of tubulin polymerization. J Med Chem 42:4081-4087 (Pubitemid 29483025)
    • (1999) Journal of Medicinal Chemistry , vol.42 , Issue.20 , pp. 4081-4087
    • Zhang, S.-X.1    Bastow, K.F.2    Tachibana, Y.3    Kuo, S.-C.4    Hamel, E.5    Mauger, A.6    Narayanan, V.L.7    Lee, K.-H.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.