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Design and Synthesis of Some Oxadiazolyl, Thiadiazolyl, Thiazolidinyl, and Thiazolyl Derivatives of 1 H ‐Pyrazole as Anti‐inflammatory Antimicrobial Agents
Author(s) -
Farghaly Ahmed A.,
Bekhit Adnan A.,
Young Park Ji
Publication year - 2000
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/(sici)1521-4184(200002)333:2/3<53::aid-ardp53>3.0.co;2-e
Subject(s) - phenacyl bromide , chemistry , pyrazole , acetic anhydride , ethyl bromoacetate , bromide , antimicrobial , medicinal chemistry , phenacyl , antifungal , organic chemistry , medicine , dermatology , catalysis
Four series of 1 H ‐pyrazole derivatives have been synthesized. The first series was prepared by cyclization of the intermediate 3‐(5‐bromo‐2‐thienyl)‐1‐phenyl‐1 H ‐pyrazole‐4‐carbaldehyde aroylhydrazone 4a—c with acetic anhydride to afford the corresponding oxadiazoline derivatives 5a—c . The other series were prepared by the cyclization of the intermediate 3‐(5‐bromo‐2‐thienyl)‐1‐phenyl‐4‐substituted thiocarbamoylhydrazonomethyl‐1 H ‐pyrazole 6a—c with acetic anhydride, ethyl bromoacetate or phenacyl bromide giving rise to 3‐(5‐bromo‐2‐thienyl)‐1‐phenyl‐4‐[3‐acetyl‐5‐( N ‐substituted acetamido)‐2,3‐dihydro‐1,3,4‐thiadiazol‐2‐yl]‐1 H ‐pyrazoles 7a—c , 3‐(5‐bromo‐2‐thienyl)‐1‐phenyl‐4‐(3‐substituted‐4‐oxothiazolidin‐2‐ylidenehydrazonomethyl)‐1 H ‐pyrazoles 8a—c , or 3‐(5‐bromo‐2‐thienyl)‐1‐phenyl‐4‐(3‐substituted‐4‐phenyl‐2,3‐dihydrothiazol‐2‐ylidenehydrazonomethyl)‐1 H ‐pyra zoles 9a—c respectively. Some of these compounds showed antiinflammatory, antibacterial or antifungal activities comparable to that of Proquazone, Ampicillin, or Clotrimazole respectively.