Anti-Inflammatory activity of newly synthesized 7-chloro-2-methyl-4H-benzo [d] [1,3]-oxazin-4-one and 3-amino-7-chloro-2-methyl-quinazolin-4(3H)-one is higher than Indomethacine

Heterocyclic chemistry comprises at least half of all organic chemistry research worldwide in particular, heterocyclic structures form the basis of many pharmaceutical, agrochemical and veterinary products. The condensation of Methyl-2-amino-4-Chlorobenzoate with acetic anhydride yielded the cyclic compound 2-methyl 7-Chloro-1, 3-benzo-oxazine-4-one (1) which further produce 3-Amino-2-Methyl 7-Chloro quinazolin-4(3H)-ones (2) via the reaction with hydrazine hydrate. The compounds synthesized were unequivocally confirmed by means of Infrared, Nuclear Magnetic Resonance (¹H and ¹³C), Gas Chromatography-Mass spectrophotometry and Elemental analysis.   Compound 1 and 2 has Anti-inflammatory activity of 96.78%, 95.71% and 97.62%, 95.35% at 10mg/kg and 20mg/Kg dose levels.  Compound 1 has IR spectrum showed signals for carbonyl functional group at 1662 cm^-1, C-O and C-H stretch vibrations at 1102 cm^-1 and 2871 cm^-1respectively. The ¹H NMR spectrum showed three aromatic protons at δ_H 7.59, 7.16 and 6.40 and a vinyl methyl protons at δ_H 2.57._.In the ¹³C NMR spectrum, the ester carbonyl resonated at δ_C 168.08, while the aromatic carbons resonated in the range δ_C 113.40 – 149.23. The resonances at δ_C 153.13 and δ_C 22.15 were due to the imine oxygenated carbon (C-1) and the methyl carbon respectively.  Compound 2, had NMR data similar to1, except for an additional signal at δ_H 5.80 in the ¹H NMR spectrum which was attributed to the amino protons (2H).  Compound 2 had a higher anti-inflammatory activity than Compound 1. The compounds synthesized had a higher anti-inflammatory activity than Indomethacin, a standard anti-inflammatory drug.

Author(s): Osarumwense Peter

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