Synthesis and pharmacological investigation of novel 3-(3-methylphenyl)-2-substituted amino-3H-quinazolin-4-ones as analgesic and anti-inflammatory agents.
A variety of novel 3-(3-methylphenyl)-2-substituted amino-3H-quinazolin-4-ones were synthesized by reacting the amino group of 2-hydrazino-3-(3-methylphenyl)-3H-quinazolin-4-one with a variety of aldehydes and ketones. The starting material 2-hydrazino-3-(3-methylphenyl)-3H-quinazolin-4-one was synthesized from 3-methyl aniline. The title compounds were investigated for analgesic, anti-inflammatory and ulcerogenic index activities. Compound 2-(1-ethylpropylidene-hydrazino)-3-(3-methylphenyl)-3H-quinazolin-4-one (AS2) was the most active analgesic agent. Compound 2-(1-methylbutylidene-hydrazino)-3-(3-methylphenyl)-3H-quinazolin-4-one (AS3) was the most active anti-inflammatory agent and was moderately more potent than the reference standard diclofenac sodium. The test compounds showed only mild ulcerogenic potential compared with aspirin.
Alagarsamy
Veerachamy
V
Medicinal Chemistry Research Laboratory, Dayananda Sagar College of Pharmacy, Kumarswamy Layout, Bangalore-560 078, India. samy_veera@yahoo.com
Dhanabal
Kumarasamy
K
Parthiban
Periyasamy
P
Anjana
Gobi
G
Deepa
Govinhan
G
Murugesan
Balakrishnan
B
Rajkumar
Subramanian
S
Beevi
Abdulrahim Janath
AJ
D000700:Analgesics / Q000009:adverse effects / Q000138:chemical synthesis* / Q000494:pharmacology*; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000009:adverse effects / Q000138:chemical synthesis* / Q000494:pharmacology*; D001241:Aspirin / Q000009:adverse effects; D002351:Carrageenan; D004008:Diclofenac / Q000494:pharmacology; D004195:Disease Models, Animal; D004305:Dose-Response Relationship, Drug; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D005260:Female; D007249:Inflammation / Q000139:chemically induced / Q000188:drug therapy; D008297:Male; D051379:Mice; D010147:Pain Measurement; D052999:Quinazolinones / Q000009:adverse effects / Q000138:chemical synthesis* / Q000494:pharmacology*; D051381:Rats; D017208:Rats, Wistar; D013276:Stomach Ulcer / Q000139:chemically induced; D013329:Structure-Activity Relationship
D000700:Analgesics; D000893:Anti-Inflammatory Agents; D052999:Quinazolinones; D004008:Diclofenac; D002351:Carrageenan; D001241:Aspirin