Orally Active. beta.-Lactam Inhibitors of Human Leukocyte Elastase. 3. Stereospecific Synthesis and Structure-Activity Relationships for 3, 3-Dialkylazetidin-2-ones

PE Finke, SK Shah, DS Fletcher, BM Ashe…

Index: Finke, Paul E.; Shah, Shrenik K.; Fletcher, Daniel S.; Ashe, Bonnie M.; Brause, Karen A.; et al. Journal of Medicinal Chemistry, 1995 , vol. 38, # 13 p. 2449 - 2462

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Citation Number: 83

Abstract

The stereospecific synthesis of several 4-[(4-carboxyphenyl) oxyl-3, 3-dialkyl-l-[~(l- phenylalkyl~-amino] carbonyllazetidin-2-ones 3 is described in which the C-3 alkyl groups were varied from methyl to butyl as well as allyl, benzyl and methoxymethyl. The structure- activity relations for these compounds are discussed in terms of the hydrolytic stability of the p-lactam ring, their in vitro inhibitory potency for human leukocyte elastase (HLE), and ...