1001525-91-2Relevant articles and documents
Cyclopropanecarboxylic acid esters as potential prodrugs with enhanced hydrolytic stability
Bender, David M.,Peterson, Jeffrey A.,McCarthy, James R.,Gunaydin, Hakan,Takano, Yu,Houk
, p. 509 - 511 (2008)
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 provides hyperconjugative stabilization.