5-substituted-1H-tetrazoles as carboxylic acid isosteres:: Medicinal chemistry and synthetic methods

被引：806

作者：

Herr, RJ ^{[1
]}

机构：

[1] Albany Med Res Inc, Dept Med Chem, Albany, NY 12212 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2002年 / 10卷 / 11期

关键词：

D O I：

10.1016/S0968-0896(02)00239-0

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

5-Substituted-1H-tetrazoles (RCN4H) are often used as metabolism-resistant isosteric replacements for carboxylic acids (RCO2H) in SAR-driven medicinal chemistry analogue syntheses. This review provides a brief summary of the medicinal chemistry of tetrazolic acids and highlights some examples of tetrazole-containing drug substances in the current literature. A survey of representative literature procedures for the preparation of 5-substituted-1H-tetrazoles, focusing on preparations from aryl and alkyl nitriles, is presented in sections by generalized synthetic methods. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3379 / 3393

页数：15

共 162 条

[21]

Butler R.N., 1996, Comprehensive Heterocyclic Chemistry II, V4, P621

[22]

Cannon J. G, 1995, BURGERS MED CHEM DRU, P783

[23] INTERACTION OF LY171883 AND OTHER PEROXISOME PROLIFERATORS WITH FATTY-ACID-BINDING PROTEIN ISOLATED FROM RAT-LIVER [J].

CANNON, JR ;

EACHO, PI .

BIOCHEMICAL JOURNAL, 1991, 280 :387-391

[24] NONPEPTIDE ANGIOTENSIN-II RECEPTOR ANTAGONISTS - THE DISCOVERY OF A SERIES OF N-(BIPHENYLYLMETHYL)IMIDAZOLES AS POTENT, ORALLY ACTIVE ANTIHYPERTENSIVES [J].

CARINI, DJ ;

DUNCIA, JV ;

ALDRICH, PE ;

CHIU, AT ;

JOHNSON, AL ;

PIERCE, ME ;

PRICE, WA ;

SANTELLA, JB ;

WELLS, GJ ;

WEXLER, RR ;

WONG, PC ;

YOO, SE ;

TIMMERMANS, PBMWM .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (08) :2525-2547

[25]

Chando TJ, 1998, DRUG METAB DISPOS, V26, P408

[26]

CHENG K, 1989, ENDOCRINOLOGY, V124, P2791

[27]

CHU S S, 1985, Drugs of the Future, V10, P632

[28] Synthesis and biological evaluation of 2-(3′-(1H-tetrazol-5-yl) bicyclo[1.1.1]pent-1-yl)glycine (S-TBPG), a novel mGlu1 receptor antagonist [J].

Costantino, G ;

Maltoni, K ;

Marinozzi, M ;

Camaioni, E ;

Prezeau, L ;

Pin, JP ;

Pellicciari, R .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (02) :221-227

[29] tris(2-perfluorohexylethyl) tin azide:: A new reagent for preparation of 5-substituted tetrazoles from nitriles with purification by fluorous organic liquid-liquid extraction [J].

Curran, DP ;

Hadida, S ;

Kim, SY .

TETRAHEDRON, 1999, 55 (29) :8997-9006

[30]

Davi H, 2000, DRUG METAB DISPOS, V28, P79

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