Design, synthesis and biological evaluation of benzimidazole/benzothiazole and benzoxazole derivatives as cyclooxygenase inhibitors

被引：301

作者：

Paramashivappa, R ^{[1
]}

Kumar, PP ^{[1
]}

Rao, PVS ^{[1
]}

Rao, AS ^{[1
]}

机构：

[1] Vittal Mallya Sci Res Fdn, Bangalore 560004, Karnataka, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2003年 / 13卷 / 04期

关键词：

D O I：

10.1016/S0960-894X(02)01006-5

中图分类号：

R914 [药物化学];

学科分类号：

100701 [药物化学];

摘要：

We have synthesised a series of 2-[[(2-alkoxy-6-pentadecylphenyl)methyl]thio]-1H-benzimidazoles benzothiazoles and benzoxazoles from anacardic acid and investigated their ability to inhibit human c cyclooxygenase-2 enzyme (COX-2). The active compounds were screened for cyclooxygenase-1 (COX-1) inhibition. Compound 13 is 384-fold and 19 is more than 470-fold selective towards COX-2 compared to COX-1. Thus. this class of compounds may serve as excellent candidates for selective COX-2 inhibition. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：657 / 660

页数：4

共 25 条

[1]

ELSHOLY MA, 1986, J MED CHEM, V29, P606

[2]

INHIBITION OF LIPOXYGENASE AND PROSTAGLANDIN ENDOPEROXIDE SYNTHASE BY ANACARDIC ACIDS [J].

GRAZZINI, R ;

HESK, D ;

HEININGER, E ;

HILDENBRANDT, G ;

REDDY, CC ;

COXFOSTER, D ;

MEDFORD, J ;

CRAIG, R ;

MUMMA, RO .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1991, 176 (02) :775-780

[3]

GULATI AS, 1964, INDIAN J CHEM, V2, P337

[4]

HERCHSMAN HR, 1996, BIOCHIM BIOPHYS ACTA, V1299, P125

[5]

HUMAN CYCLOOXYGENASE-2 CDNA [J].

HLA, T ;

NEILSON, K .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1992, 89 (16) :7384-7388

[6]

KIONG LS, 1971, J CHEM SOC P1, P1942

[7]

(H+,K+)-ATPASE INHIBITING 2-[(2-PYRIDYLMETHYL)SULFINYL]BENZIMIDAZOLES .4. A NOVEL SERIES OF DIMETHOXYPYRIDYL-SUBSTITUTED INHIBITORS WITH ENHANCED SELECTIVITY - THE SELECTION OF PANTOPRAZOLE AS A CLINICAL CANDIDATE [J].

KOHL, B ;

STURM, E ;

SENNBILFINGER, J ;

SIMON, WA ;

KRUGER, U ;

SCHAEFER, H ;

RAINER, G ;

FIGALA, V ;

KLEMM, K ;

IFE, RJ ;

LEACH, CA .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (06) :1049-1057

[8]

TYROSINASE INHIBITORS FROM ANACARDIUM-OCCIDENTALE FRUITS [J].

KUBO, I ;

KINSTHORI, I ;

YOKOKAWA, Y .

JOURNAL OF NATURAL PRODUCTS, 1994, 57 (04) :545-551

[9]

Kubuju D. A., 1991, J BIOL CHEM, V266, P12866

[10]

Synthesis and evaluation of a new class of nifedipine analogs with T-type calcium channel blocking activity [J].

Kumar, PP ;

Stotz, SC ;

Paramashivappa, R ;

Beedle, AM ;

Zamponi, GW ;

Rao, AS .

MOLECULAR PHARMACOLOGY, 2002, 61 (03) :649-658

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