Synthesis and porcine pancreatic elastase inhibitory evaluation of 6α-(sulfonyl)oxy-and 6α-chloropenicillanate sulfone esters and 3α-(acyloxy)methyl-6α-chloropenam sulfones
作者： Carlos E. Boschetti , Ernesto G. Mata , Oreste A. Mascaretti , Julia A. Cricco , Gabriela Coux
DOI: 10.1016/0960-894X(95)00347-V
关键词: Pancreatic elastase 、 Sulfonyl 、 Pivaloyloxymethyl 、 Chemistry 、 Elastase 、 Organic chemistry 、 Sulfone 、 Inhibitory postsynaptic potential
摘要: Abstract The synthesis of 6α-chloropenicillanate sulfone esters 4a-c, 9, the acetate and benzoate 3α-hydroxymethyl-6α-chloropenam sulfones 6a-b pivaloyloxymethyl benzyl several 6α-(sulfonyl)oxypenicillanate 12, 15a1-a3, 15b1-b3 are reported. When tested as inhibitors porcine pancreatic elastase, 3α-hydroxymethylpenam 6a proved to be more active in comparison with 3α-carboxylic acid counterparts 4a-c 9. Compounds diverse 6α-(sulfonyl)oxy substituents showed elastase inhibitory activity improved over corresponding 6α-chloro derivatives 9; among those, compounds 15a2 15b2 were rather unstable, but 15a1, 15a3, 15b1, 15b3 combined fair better stability.
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