Open AccessSynthesis and Inhibition of Human Leucocyte Elastase by Functionalized N ‐Aryl Azetidin‐2‐ones: Effect of Different Substituents on the Aromatic Ring
Author(s) -
Joyeau R.,
Felk A.,
Guilaume S.,
Wakselman M.,
Vergely I.,
Doucet C.,
Boggetto N.,
ReboudRavaux M.
Publication year - 1996
Publication title -
journal of pharmacy and pharmacology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.745
H-Index - 118
eISSN - 2042-7158
pISSN - 0022-3573
DOI - 10.1111/j.2042-7158.1996.tb03927.x
Subject(s) - moiety , aryl , elastase , chemistry , ring (chemistry) , substituent , alkyl , stereochemistry , electrophile , enzyme , medicinal chemistry , organic chemistry , catalysis
N ‐aryl‐3,3‐difluoroazetidin‐2‐ones featured by a latent electrophilic methylene quinoniminium function have been synthesized and evaluated as inhibitors of human leucocyte elastase. To promote hydrophobic interactions with the enzyme, to increase the rates of β‐lactam ring opening and of benzylic group departure, or to induce hydrosolubility, these compounds incorporate on their aromatic ring either an alkyl moiety, a methoxy substituent or a carboxylic group. Some of these β‐lactams proved to be good inactivators of human leucocyte elastase.