Synthesis and Anti-Inflammatory, Analgesic, Ulcerogenic and Cyclooxygenase-Ii Inhibitory Activities of Indolyl -Pyrazolines and Indolylthiazolidinyl Pyrazolines

Ashok Kumar et al.

Department of Pharmacology, LLRM Medical College, Meerut - 250 004 (India)

A series of 1-Acetyl-3[p-{2'-(2-chlorophenyl)-5""-methoxyindol-3""-yl)-4'-oxo-1'-thiazolidin-3-yl}phenyl]-5-substitutedphenyl-2-pyrazolines (22-31) and-3-[p-{2'-(2""-chlorophenyl)-5""-methoxyindol-3""-yl)-4'-oxo-5'-1'-thiazolidin-3'-yl}phenyl]-5-substitute-dphenyl-2-pyrazolines (42-51) have been synthesized by the condensation of thiolactic/thioglycolic acid with 1-acetyl-5-substitutedphenyl-3-[4'-{2""-(p-chlorophenyl)-5""-methoxyindol-3""-yl}methylimino}phenyl]-2-pyrazolines (12-21) and 1-substituted phenyl-3-[p-{(2'-(p-chlorophenyl)-5'-methoxyindol-3'-yl)methylimino} phenyl]-5-subst-itutedphenyl-2-pyrazolines (32-41), respectively. The compounds 12-21 and compounds 32-41 have been prepared by the reaction of hydrazine hydrate and substitutedph-enylhydrazine with compounds 2-11 respectively. The structures of the compounds were established on the basis of elemental analysis and spectral studies. The newly synthesized compounds were evaluated for their anti-inflammatory activity against carrageenan induced oedema test, analgesic, ulcerogenic liabilities and cyclooxygenase II-inhibitory activities. Compounds 29 and 49 were found to be potent members of the present series, which showed 68.3% and 61.8% anti-inflammatory activity, respectively at a dose of 50 mg/kg p.o., while standard drug Phenylbutazone exhibited 36.4% and Aspirin exhibited 38.4% anti-inflammatory activity at same dose. However compound 29, was found to be most active and less ulcerogenic compound of this series. The structure of these compounds have been elucidated by IR, 1H NMR, mass spectroscopy and elemental analysis."

5-Methoxy p-chlorophenylchalcones; 5-methoxy p-chlorophenylpyrazolines; 5-methoxy p-chlorophenylthiazolidinone; Anti-inflammatory activity