Synthesis of 3-[4'-(p-chlorophenyl)-thiazol-2'-yl]-2-[(substituted azetidinone/thiazolidinone)-aminomethyl]-6-bromoquinazolin-4-ones as anti-inflammatory agent.
N-Chloroacetyl-5-bromoanthranilic acid (1), 3-[4'-(p-chlorophenyl)-thiazol-2'-yl]-2-chloromethyl-6-bromoquinazolin-4-one (2), 3-[4'-(p-chlorophenyl)-thiazol-2'-yl]-2-hydrazinomethyl-6-bromoquinazolin-4-one (3), 3-[4'-(p-chlorophenyl)-thiazol-2'-yl]-2-substitutedbenzylidene aminomethyl-6-bromoquinazolin-4-ones (4-11), 2-[(4'-oxo-3'-chloro-2'-phenylazetidin-1'-yl)aminomethyl]-3-[4''-(p-chlorophenyl)thiazol-2''-yl]-6-bromoquinazolin-4-ones (12-19) and 2-(4'-oxo-2'-phenyl-thiazolidin-3'-yl-aminomethyl)- 3-[4''-(p-chlorophenyl)-thiazol-2''-yl]-6-bromoquinazolin-4-ones (20-27) have been synthesized. All the compounds have been screened for their anti-inflammatory and analgesic activities at the dose of 50mg/kg po. Compound 21 showed maximum anti-inflammatory (38.35%) and analgesic (37.36%) activities. Compound 21 was also tested for ulcerogenic activity and the UD(50) value was found to be 195.6mg/kg po. The structure of all compounds has been evaluated by elemental analysis (C, H, N) and spectral analysis (IR, (1)H NMR and mass spectrometry).
Kumar
Ashok
A
Department of Pharmacology, L L R M Medical College, Meerut (UP) 250004, India.
Rajput
Chatrasal Singh
CS
Bhati
Sudhir Kumar
SK
D019342:Acetic Acid; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000009:adverse effects / Q000138:chemical synthesis* / Q000494:pharmacology*; D001384:Azetidines / Q000138:chemical synthesis* / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D005260:Female; D007202:Indicators and Reagents; D007928:Lethal Dose 50; D008297:Male; D010147:Pain Measurement / Q000187:drug effects; D052999:Quinazolinones / Q000138:chemical synthesis* / Q000494:pharmacology*; D051381:Rats; D013276:Stomach Ulcer / Q000139:chemically induced / Q000473:pathology
C116379:2-azetidinone; D000894:Anti-Inflammatory Agents, Non-Steroidal; D001384:Azetidines; D007202:Indicators and Reagents; D052999:Quinazolinones; D019342:Acetic Acid