66317-01-9Relevant academic research and scientific papers
A series of penicillin derived C2-symmetric inhibitors of HIV-1 proteinase: synthesis, mode of interaction, and structure-activity relationships.
Humber,Bamford,Bethell,Cammack,Cobley,Evans,Gray,Hann,Orr,Saunders,et al.
, p. 3120 - 3128 (2007/10/02)
The C2-symmetric diester 1 was identified by random screening as a novel inhibitor of HIV-1 proteinase. This led to the preparation of a series of related more potent amides from readily accessible penicillins. Many of the compounds showed potent antivira
Thiazolidine Ring Opening in Penicillin Derivatives. Part 2. Enamine Formation
Davis, Andrew M.,Layland, Nicola J.,Page, Michael I.,Martin, Frances,O'Ferrall, Rory More
, p. 1225 - 1229 (2007/10/02)
The alkaline hydrolysis of (3S,5R,6R)-methyl benzylpenicilloate, and the corresponding carboxamide and N-ethylamide, is accompanied by an absorbance increase at 285 nm.This is attributed to a competing elimination reaction across C6-C5 to open the thiazolidine ring and reversibly generate an enamine intermediate.Kinetic analysis and hydrolysis in D2O do not indicate a significant buildup of this intermediate during hydrolysis of the methyl ester.However, over the pH range 4-11 the rate of thiazolidine ring opening is competitive with hydrolysis of the ester function.The deuterium solvent kinetic isotope effect on the ring closure reaction is 7.5.
