Synthesis and pharmacological evaluation of some novel 2-(5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(coumarin-3-yl)thiazoles

被引：110

作者：

Aggarwal, Ranjana ^{[1
]}

Kumar, Sunil ^{[1
]}

Kaushik, Pawan ^{[2
]}

Kaushik, Dhirender ^{[2
]}

Gupta, Girish Kumar ^{[3
]}

机构：

[1] Kurukshetra Univ, Dept Chem, Kurukshetra 136119, Haryana, India

[2] Kurukshetra Univ, Dept Pharmaceut Sci, Kurukshetra 136119, Haryana, India

[3] MM Univ, MM Coll Pharm, Mullana 133203, Ambala, India

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2013年 / 62卷

关键词：

3-(2-Bromoacetyl)coumarins; 2-(5-Hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(coumarin-3-yl) thiazoles; Anti-inflammatory activity; Antibacterial activity; TRIFLUOROMETHYL-BETA-DIKETONES; ANTIBACTERIAL ACTIVITY; INHIBITORS; DESIGN; DERIVATIVES; THIAZOLES; AGENTS; DEHYDRATION; ANTICANCER; ANTITUMOR;

D O I：

10.1016/j.ejmech.2012.11.046

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of novel 2-(5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(coumarin-3-yl)thiazoles (6) were synthesized by condensing 3-(2-bromoacetyl)coumarins (4) with various 5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-thiocarboxamides (5), obtained by the reaction of thiosemicarbazide with trifluoromethyl-beta-diketones. All the tested compounds displayed significant to moderate in vivo anti-inflammatory activity when compared to the standard drug indomethacin, and good broad spectrum in vitro antibacterial activity against three Gram-positive and four Gram-negative bacteria when compared with cefixime. (C) 2013 Elsevier Masson SAS. All rights reserved.

引用

页码：508 / 514

页数：7

共 40 条

[21] SYNTHESIS OF 2,4-DISUBSTITUTED THIAZOLES AND SELENAZOLES AS POTENTIAL ANTITUMOR AND ANTIFILARIAL AGENTS .1. METHYL 4-(ISOTHIOCYANATOMETHYL)THIAZOLE-2-CARBAMATES, -SELENAZOLE-2-CARBAMATES, AND RELATED DERIVATIVES [J].

KUMAR, Y ;

GREEN, R ;

BORYSKO, KZ ;

WISE, DS ;

WOTRING, LL ;

TOWNSEND, LB .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (24) :3843-3848

[22] A NOVEL SYNTHESIS AND POTENT ANTIINFLAMMATORY ACTIVITY OF 4-HYDROXY-2(1H)-OXO-1-PHENYL-1,8-NAPHTHYRIDINE-3-CARBOXAMIDES [J].

KURODA, T ;

SUZUKI, F ;

TAMURA, T ;

OHMORI, K ;

HOSOE, H .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (06) :1130-1136

[23] DNA gyrase interaction with coumarin-based inhibitors:: The role of the hydroxybenzoate isopentenyl moiety and the 5′-methyl group of the noviose [J].

Lafitte, D ;

Lamour, V ;

Tsvetkov, PO ;

Makarov, AA ;

Klich, M ;

Deprez, P ;

Moras, D ;

Briand, C ;

Gilli, R .

BIOCHEMISTRY, 2002, 41 (23) :7217-7223

[24]

Mutlu D. A., 2003, TURK J CHEM, V27, P757

[25]

NCCLS, 2000, METHOD FOR DILUTION

[26]

Pathak R.B., 1981, BOKIN BOBAI, V9, P477

[27] Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib) [J].

Penning, TD ;

Talley, JJ ;

Bertenshaw, SR ;

Carter, JS ;

Collins, PW ;

Docter, S ;

Graneto, MJ ;

Lee, LF ;

Malecha, JW ;

Miyashiro, JM ;

Rogers, RS ;

Rogier, DJ ;

Yu, SS ;

Anderson, GD ;

Burton, EG ;

Cogburn, JN ;

Gregory, SA ;

Koboldt, CM ;

Perkins, WE ;

Seibert, K ;

Veenhuizen, AW ;

Zhang, YY ;

Isakson, PC .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (09) :1347-1365

[28] 1,2,4-TRIAZOLES .32. SYNTHESES AND CORRELATION OF PROTON MAGNETIC-RESONANCE SPECTRAL CHARACTERISTICS WITH MOLECULAR-ORBITAL PARAMETERS OF DERIVATIVES OF S-TRIAZOLO[4,3-A]QUINOLINE AND S-TRIAZOLO[3,4-A]ISOQUINOLINE RING-SYSTEMS [J].

POTTS, KT ;

BHATTACH.J ;

SMITH, SL ;

IHRIG, AM ;

GIRARD, CA .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (26) :4410-4415

[29] Pyrazolo[1,5-a]pyrimidines.: A combined multinuclear magnetic resonance (1H, 13C, 15N, 19F) and DFT approach to their structural assignment [J].

Sanz, Dionisia ;

Claramunt, Rosa M. ;

Saini, Anil ;

Kumar, Vinod ;

Aggarwal, Ranjana ;

Singh, Shiv P. ;

Alkorta, Ibon ;

Elguero, Jose .

MAGNETIC RESONANCE IN CHEMISTRY, 2007, 45 (06) :513-517

[30] Synthesis of 4-benzyl-1,3-thiazole derivatives as potential anti-inflammatory agents: An analogue-based drug design approach [J].

Sharma, Ritesh N. ;

Xavier, Franklin P. ;

Vasu, Kamala K. ;

Chaturvedi, Subhash C. ;

Pancholi, Shyam S. .

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2009, 24 (03) :890-897

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