Coumarinyl pyrazole derivatives of INH: promising antimycobacterial agents

被引：31

作者：

Aragade, Prashant ^{[1
]}

Palkar, Mahesh ^{[1
]}

Ronad, Pradeepkumar ^{[1
]}

Satyanarayana, Darbhamulla ^{[2
]}

机构：

[1] KLES Coll Pharm, Dept Med Chem, Hubli, Karnataka, India

[2] NGSM Inst Pharmaceut Sci, Dept Med Chem, Mangalore, Karnataka, India

来源：

MEDICINAL CHEMISTRY RESEARCH | 2013年 / 22卷 / 05期

关键词：

Antimycobacterial activity; Coumarin; Isonicotinic acid hydrazide; Pyrazole; Mycobacterium tuberculosis; MYCOBACTERIUM-TUBERCULOSIS; ANTIBACTERIAL ACTIVITY; SERIES;

D O I：

10.1007/s00044-012-0222-8

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The purpose of this study was to evaluate the antimycobacterial activity of various pyrazole derivatives derived from the isoniazid pharmacophore along with coumarin scaffold. The synthesized title compounds (4a-4k) were investigated for their in vitro antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv using Resazurin MIC assay. The synthesized compounds exhibited MIC ranging from 0.625 to 2.50 mu g/ml. Among the series tested, compound 3-[3-(4-fluorophenyl)-1-isonicotinoyl-1H-pyrazol-5-yl]-2H-chromen-2-one 4i was found to be the most active with MIC of 0.625 mu g/ml.

引用

页码：2279 / 2283

页数：5

共 24 条

[1] Synthesis, structural activity relationship and anti-tubercular activity of novel pyrazoline derivatives [J].

Ali, Mohamed Ashraf ;

Shaharyar, Mohammad ;

Siddiqui, Anees Ahamed .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2007, 42 (02) :268-275

[2] Synthesis and Antibacterial Activity of a New Series of 3-[3-(Substituted Phenyl)-1-Isonicotinoyl-1H-Pyrazol-5-yl]-2H-Chromen-2-one Derivatives [J].

Aragade, Prashant ;

Maddi, Veeresh ;

Khode, Suresh ;

Palkar, Mahesh ;

Ronad, Pradeepkumar ;

Mamledesai, Shivalingarao ;

Satyanarayana, Darbhamulla .

ARCHIV DER PHARMAZIE, 2009, 342 (06) :361-366

[3]

Bolakatti GS, 2008, ARZNEIMITTELFORSCH, V58, P515, DOI 10.1055/s-0031-1296551

[4] MYCOBACTERIAL DISEASE, IMMUNOSUPPRESSION, AND ACQUIRED IMMUNODEFICIENCY SYNDROME [J].

COLLINS, FM .

CLINICAL MICROBIOLOGY REVIEWS, 1989, 2 (04) :360-377

[5] Microplate Alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium [J].

Collins, LA ;

Franzblau, SG .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1997, 41 (05) :1004-1009

[6] CRYSTAL-STRUCTURE AND FUNCTION OF THE ISONIAZID TARGET OF MYCOBACTERIUM-TUBERCULOSIS [J].

DESSEN, A ;

QUEMARD, A ;

BLANCHARD, JS ;

JACOBS, WR ;

SACCHETTINI, JC .

SCIENCE, 1995, 267 (5204) :1638-1641

[7] Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl)oxazolidinones with expanded activity against the fastidious gram-negative organisms Haemophilus influenzae and Moraxella catarrhalis [J].

Genin, MJ ;

Allwine, DA ;

Anderson, DJ ;

Barbachyn, MR ;

Emmert, DE ;

Garmon, SA ;

Graber, DR ;

Grega, KC ;

Hester, JB ;

Hutchinson, DK ;

Morris, J ;

Reischer, RJ ;

Ford, CW ;

Zurenko, GE ;

Hamel, JC ;

Schaadt, RD ;

Stapert, D ;

Yagi, BH .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (05) :953-970

[8] Effect of isoniazid chemoprophylaxis on HIV-related mycobacterial disease [J].

Graham, NMH ;

Galai, N ;

Nelson, KE ;

Astemborski, J ;

Bonds, M ;

Rizzo, RT ;

Sheeley, L ;

Vlahov, D .

ARCHIVES OF INTERNAL MEDICINE, 1996, 156 (08) :889-894

[9] Randomised trial of isoniazid versus rifampicin and pyrazinamide for prevention of tuberculosis in HIV-1 infection [J].

Halsey, NA ;

Coberly, JS ;

Desormeaux, J ;

Losikoff, P ;

Atkinson, J ;

Moulton, LH ;

Contave, M ;

Johnson, M ;

Davis, H ;

Geiter, L ;

Johnson, E ;

Huebner, R ;

Boulos, R ;

Chaisson, RE .

LANCET, 1998, 351 (9105) :786-792

[10] THE MYCOBACTERIUM-AVIUM COMPLEX [J].

INDERLIED, CB ;

KEMPER, CA ;

BERMUDEZ, LEM .

CLINICAL MICROBIOLOGY REVIEWS, 1993, 6 (03) :266-310

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