5-Substituted-1H-tetrazoles as carboxylic acid isosteres: medicinal chemistry and synthetic methods.
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.
Herr
R Jason
RJ
Medicinal Chemistry Department, Albany Molecular Research, Inc., PO Box 15098, Albany, NY 12212-5098, USA. rjasonh@albmolecular.com
D000818:Animals; D001386:Azides / Q000138:chemical synthesis / Q000494:pharmacology; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000494:pharmacology*; D002626:Chemistry, Pharmaceutical; D006801:Humans; D007536:Isomerism; D012825:Silicon / Q000737:chemistry; D013777:Tetrazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D014001:Tin / Q000737:chemistry
D001386:Azides; D002264:Carboxylic Acids; D013777:Tetrazoles; C007972:hydrazoic acid; D014001:Tin; D012825:Silicon