Cyclopropanecarboxylic acid esters as potential prodrugs with enhanced hydrolytic stability

…, JR McCarthy, H Gunaydin, Y Takano, KN Houk

Index: Bender, David M.; Peterson, Jeffrey A.; McCarthy, James R.; Gunaydin, Hakan; Takano, Yu; Houk Organic Letters, 2008 , vol. 10, # 3 p. 509 - 511

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Citation Number: 27

Abstract

Esters of cyclopropanecarboxylic acid demonstrate a substantial increase in stability under both acid-and base-catalyzed hydrolytic conditions. Comparison of the stability of valacyclovir 13 with the cyclopropane analogue 14 shows that at 40° C and pH 6 the half-life of 14 is> 300 h while the value for 13 is 69.7 h. CBS-QB3 calculations on isodesmic reactions for transfer of groups from an alkane to an ester show that a cyclopropyl group ...

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