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Design and synthesis of some oxadiazolyl, thiadiazolyl, thiazolidinyl, and thiazolyl derivatives of 1H-pyrazole as anti-inflammatory antimicrobial agents

Authors
Farghaly, AABekhit, AAPark, JY
Issue Date
Mar-2000
Publisher
WILEY-V C H VERLAG GMBH
Keywords
oxadiazolyl; thiadiazolyl; thiazolidinyl; thiazolyl; pyrazole; anti-inflammatory; antimicrobial
Citation
ARCHIV DER PHARMAZIE, v.333, no.2-3, pp.53 - 57
Journal Title
ARCHIV DER PHARMAZIE
Volume
333
Number
2-3
Start Page
53
End Page
57
URI
https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/16782
DOI
10.1002/(SICI)1521-4184(200002)333:2/3<53::AID-ARDP53>3.3.CO;2-5
ISSN
0365-6233
Abstract
Four series of 1H-pyrazole derivatives have been synthesized. The first series was prepared by cyclization of the intermediate 3-(5-bromo-2-thienyl)-1-phenyl-1H-pyrazole-4-carbaldehyde aroyl-hydrazone 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-1H-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]pyrazoles 7a-c, 3-(5-bromo-2-thienyl)-1-phenyl-4-(3-substituted-4-oxothiazolidin- 2- ylidenehydrazonomethyl)-1H-pyrazoles 8a-c, or 3-(5-bromo-2-thienyl)-1-phenyl-4-(3-substituted-4-phenyl-2,3 -dihydrothiazol-2-ylidenehydrazonomethyl)-1H-pyra zoles 9a-c respectively. Some of these compounds showed anti-inflammatory, antibacterial or antifungal activities comparable to that of Proquazone, Ampicillin, or Clolrimazole respectively.
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