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Volumn 21, Issue 2, 2012, Pages 185-191

An efficient one-pot cyclization of quinoline thiosemicarbazones to quinolines derivatized with 1,3,4-thiadiazole as anticancer and anti-tubercular agents

Author keywords

1,3,4 Thiadiazole; Anticancer activity; Antitubercular activity; C log P; Cyclization; Quinoline; SAR

Indexed keywords

1,3,4 THIADIAZOLE DERIVATIVE; ACETIC ANHYDRIDE; ANTINEOPLASTIC AGENT; N [4 ACETYL 5(2 CHLORO 6 METHOXYQUINOLIN 3 YL) 4,5 DIHYDRO 1,3,4 THIADIAZOL 2 YL] ACETAMIDE; N [4 ACETYL 5(2 CHLORO 6 METHYLQUINOLIN 3 YL) 4,5 DIHYDRO 1,3,4 THIADIAZOL 2 YL] ACETAMIDE; N [4 ACETYL 5(2 CHLORO 6,7 DIMETHOXYQUINOLIN 3 YL) 4,5 DIHYDRO 1,3,4 THIADIAZOL 2 YL] ACETAMIDE; N [4 ACETYL 5(2 CHLORO 7 METHOXYQUINOLIN 3 YL) 4,5 DIHYDRO 1,3,4 THIADIAZOL 2 YL] ACETAMIDE; N [4 ACETYL 5(2 CHLORO 7 METHYLQUINOLIN 3 YL) 4,5 DIHYDRO 1,3,4 THIADIAZOL 2 YL] ACETAMIDE; N [4 ACETYL 5(2 CHLORO 8 METHOXYQUINOLIN 3 YL) 4,5 DIHYDRO 1,3,4 THIADIAZOL 2 YL] ACETAMIDE; N [4 ACETYL 5(2 CHLORO 8 METHYLQUINOLIN 3 YL) 4,5 DIHYDRO 1,3,4 THIADIAZOL 2 YL] ACETAMIDE; N [4 ACETYL 5(2 CHLOROQUINOLIN 3 YL) 4,5 DIHYDRO 1,3,4 THIADIAZOL 2 YL] ACETAMIDE; N [4 ACETYL 5(2,6 DICHLOROQUINOLIN 3 YL) 4,5 DIHYDRO 1,3,4 THIADIAZOL 2 YL] ACETAMIDE; N [4 ACETYL 5(6 BROMO 2 CHLOROQUINOLIN 3 YL) 4,5 DIHYDRO 1,3,4 THIADIAZOL 2 YL] ACETAMIDE; QUINOLINE DERIVATIVE; THIOSEMICARBAZONE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

EID: 84861880315     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-010-9522-z     Document Type: Article
Times cited : (51)

References (18)
  • 3
    • 77954349652 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of new 2-chloro-3-((4-phenyl-1H-1, 2, 3-triazol-yl)-methyl)-quinoline derivatives via click chemistry approach
    • Kategaonkar A, Shinde PV, Kategaonkar AH, Pasale SK, Shingate BB (2010) Synthesis and biological evaluation of new 2-chloro-3-((4-phenyl-1H-1, 2, 3-triazol-yl)-methyl)-quinoline derivatives via click chemistry approach. Eur J Med Chem 45:3142-3146
    • (2010) Eur J Med Chem , vol.45 , pp. 3142-3146
    • Kategaonkar, A.1    Shinde, P.V.2    Kategaonkar, A.H.3    Pasale, S.K.4    Shingate, B.B.5
  • 4
    • 65349113632 scopus 로고    scopus 로고
    • Synthesis and antimicrobial studies of novel methylene bridged benzisoxazolyl imidazo-[2,1-b][1,3,4]-thiadiazole derivatives
    • Lamani RS, Shetty NS, Kamble RR, Khazi IA (2009) Synthesis and antimicrobial studies of novel methylene bridged benzisoxazolyl imidazo-[2,1-b][1,3,4]-thiadiazole derivatives. Eur J Med Chem 44:2828-2833
    • (2009) Eur J Med Chem , vol.44 , pp. 2828-2833
    • Lamani, R.S.1    Shetty, N.S.2    Kamble, R.R.3    Khazi, I.A.4
  • 5
    • 0023022233 scopus 로고
    • Cardiotonic agents. 1. Synthesis and structure-activity relationships in a new class of 3-, 4-, and 5-pyridyl-2(1H)-quinolone derivatives
    • DOI 10.1021/jm00162a002
    • Leclerc G, Marciniak G, Decker N, Schwartz J (1986) Cardiotonic agents. 1. Synthesis and structure activity relationships in a new class of 3-, 4-, and 5-pyridyl-2(1H)-quinolone derivatives. J Med Chem 29:2427-2432 (Pubitemid 17211400)
    • (1986) Journal of Medicinal Chemistry , vol.29 , Issue.12 , pp. 2427-2432
    • Leclerc, G.1    Marciniak, G.2    Decker, N.3    Schwartz, J.4
  • 6
    • 64549094601 scopus 로고    scopus 로고
    • Structure-activity relationships for a series of quinoline-based compounds active against replicating and nonreplicating Mycobacterium tuberculosis
    • Lilienkampf A, Mao J, Wan B, Wang Y, Franzblau SG, Kozikowski AP (2009) Structure-activity relationships for a series of quinoline-based compounds active against replicating and nonreplicating Mycobacterium tuberculosis. J Med Chem 52:2109-2118
    • (2009) J Med Chem , vol.52 , pp. 2109-2118
    • Lilienkampf, A.1    Mao, J.2    Wan, B.3    Wang, Y.4    Franzblau, S.G.5    Kozikowski, A.P.6
  • 7
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • DOI 10.1016/S0169-409X(96)00423-1, PII S0169409X96004231
    • Lipinski A, Franco L, Dominy BW, Feeney PJ (1997) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 23:3-25 (Pubitemid 27046991)
    • (1997) Advanced Drug Delivery Reviews , vol.23 , Issue.1-3 , pp. 3-25
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 8
    • 67349184775 scopus 로고    scopus 로고
    • Synthesis of new chiral 2,5-disubstituted 1,3,4-thiadiazoles possessing c-butenolide moiety and preliminary evaluation of in vitro anticancer activity
    • Meng XW, Lei F, Xue QL, Xue-Zhang Z, Zhi HS (2009) Synthesis of new chiral 2,5-disubstituted 1,3,4-thiadiazoles possessing c-butenolide moiety and preliminary evaluation of in vitro anticancer activity. Eur J Med Chem 44:3340-3344
    • (2009) Eur J Med Chem , vol.44 , pp. 3340-3344
    • Meng, X.W.1    Lei, F.2    Xue, Q.L.3    Xue-Zhang, Z.4    Zhi, H.S.5
  • 9
    • 33645821103 scopus 로고    scopus 로고
    • Synthesis and antimycobacterial activities of certain trifluoromethyl- aminoquinoline derivatives
    • Mital A, Negi VS, Ramachandran U (2006) Synthesis and antimycobacterial activities of certain trifluoromethyl-aminoquinoline derivatives. ARKIVOC x:220-227 (Pubitemid 43570425)
    • (2006) Arkivoc , vol.2006 , Issue.10 , pp. 220-227
    • Mital, A.1    Negi, V.S.2    Ramachandran, U.3
  • 10
    • 42249094251 scopus 로고    scopus 로고
    • Synthesis and anti-tuberculosis activity of 2,4- disubstituted quinolines
    • Nayar A, Jain R (2008) Synthesis and anti-tuberculosis activity of 2,4- disubstituted quinolines. Indian J Chem 47B:117-128
    • (2008) Indian J Chem , vol.47 B , pp. 117-128
    • Nayar, A.1    Jain, R.2
  • 11
    • 0000525422 scopus 로고
    • New synthesis of quinoline, thienopyrimidine and related fused pyridines
    • Otto MC, Bramha NA (1978) New synthesis of quinoline, thienopyrimidine and related fused pyridines. Tetrahedron Lett 23: 2045-2048
    • (1978) Tetrahedron Lett , vol.23 , pp. 2045-2048
    • Otto, M.C.1    Bramha, N.A.2
  • 12
    • 37049092925 scopus 로고
    • A versatile new synthesis and related fused pyridines. Part 5. The synthesis of 2-chloroquinoline-3-carbaldehydes
    • Otto MC, Bramha NA (1981) A versatile new synthesis and related fused pyridines. Part 5. The synthesis of 2-chloroquinoline-3-carbaldehydes. J Chem Soc Perkin Trans 1:1520-1530
    • (1981) J Chem Soc Perkin Trans , vol.1 , pp. 1520-1530
    • Otto, M.C.1    Bramha, N.A.2
  • 13
    • 77955552938 scopus 로고    scopus 로고
    • Synthesis and bioassay of aminosulfonyl-1,3,4-oxadiazoles and their interconversion to 1,3,4-thiadiazoles
    • Padmavathi V, Reddy SN, Reddy GD, Padmaja A (2010) Synthesis and bioassay of aminosulfonyl-1,3,4-oxadiazoles and their interconversion to 1,3,4-thiadiazoles. Eur J Med Chem 45(9): 4246-4251
    • (2010) Eur J Med Chem , vol.45 , Issue.9 , pp. 4246-4251
    • Padmavathi, V.1    Reddy, S.N.2    Reddy, G.D.3    Padmaja, A.4
  • 14
    • 33748157485 scopus 로고    scopus 로고
    • Synthesis and antibacterial activities of α-hydroxyphosphonates and α-acetyloxyphosphonates derived from 2-chloroquinoline-3-carbaldehyde
    • Pokalwar RU, Hangarge RV, Maskeb PV, Shingare MS (2006) Synthesis and antibacterial activities of a-hydroxyphosphonates and acetyloxyphosphonates derived from 2-chloroquinoline-3-carbaldehyde. ARKIVOC xii:196-204 (Pubitemid 44315883)
    • (2006) Arkivoc , vol.2006 , Issue.11 , pp. 196-204
    • Pokalwar, R.U.1    Hangarge, R.V.2    Maske, P.V.3    Shingare, M.S.4
  • 15
    • 33748993964 scopus 로고    scopus 로고
    • Synthesis and antituberculosis activity of 2-(aryl/alkylamino)-5-(4- aminophenyl)-1,3,4-thiadiazoles and their Schiff bases
    • Solak S, Rollas S (2006) Synthesis and antituberculosis activity of 2-(aryl/alkylamino)-5-(4-aminophenyl)-1,3,4-thiadiazoles and their Schiff bases. ARKIVOC 12:173-181 (Pubitemid 44453881)
    • (2006) Arkivoc , vol.2006 , Issue.12 , pp. 173-181
    • Solak, N.1    Rollas, S.2
  • 16
    • 84988129057 scopus 로고
    • Optimization of parameters for semi empirical methods i
    • Stewart JP (1989) Optimization of parameters for semi empirical methods I. Method J Comput Chem 10:209-220
    • (1989) Method J Comput Chem , vol.10 , pp. 209-220
    • Stewart, J.P.1
  • 17
    • 0038690647 scopus 로고
    • Indiana University, Bloomington (IN 47405)
    • Stewart JP (1990) MOPAC 6.0 QCPE 455. Indiana University, Bloomington (IN 47405)
    • (1990) MOPAC 6.0 QCPE 455
    • Stewart, J.P.1
  • 18
    • 2142662107 scopus 로고    scopus 로고
    • Ring-substituted quinolines as potential anti-tuberculosis agents
    • DOI 10.1016/j.bmc.2004.03.045, PII S0968089604002470
    • Vangapandu S, Jain M, Jain R, Kaur S, Singh PP (2004) Ringsubstituted quinolines as potential anti-tuberculosis agents. Bioorg Med Chem 12:2501-2508 (Pubitemid 38542774)
    • (2004) Bioorganic and Medicinal Chemistry , vol.12 , Issue.10 , pp. 2501-2508
    • Vangapandu, S.1    Jain, M.2    Jain, R.3    Kaur, S.4    Singh, P.P.5


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