Synthesis and porcine pancreatic elastase inhibitory evaluation of esters of several 6*-(sulfonyl)oxy-, 6*-chloropenicillanate sulfones, and 3*-(acyloxy)methilpenam sulfones.

BOSCHETTI,; MATA, E. G.; MASCARETTI, O. A.; CRICCO, J. A.; GABRIELA COUX; ROVERI, O. A.

Bioorganic & Medicinal Chemistry Letters

Elsevier

Año: 1995 vol. 5 p. 2033 - 2035

Abstract: The synthesis of 6o~-chloropenicillanate sulfone esters 4a.c, 9, the acetate and benzoate of 3ahydroxymethyl-6o~-chloropenam sulfones 6a-b and pivaloyloxymethyl and benzyl esters of several 6c~-(sulfonyl)oxypenicillanate sulfones 12, 15al-a3, 15bl-b3 are reported. When tested as inhibitors ofporcine pancreatic elastase, the acetate of 3o~-hydroxymethylpenam 6a proved to be more active in comparisonwith the esters of 3a-carboxylic acid counterparts 4a-c and 9. Compounds with diverse 6o~-(sulfonyl)oxysubstituents showed elastase inhibitory activity improved over the con´esponding 6a-chloro derivatives 4a-cand 9; among those, compounds 15a2 and 1562 were rather unstable, but compounds 15al, 15a3, 15bl,15b3 combined fair activity with better stability.