Tetrazolo[1,5-a]quinoline as a potential promising new scaffold for the synthesis of novel anti-inflammatory and antibacterial agents.
Three series of tetrazolo[1,5-a]quinoline derivatives have been synthesized. The first series was synthesized starting by the condensation of tetrazolo[1,5-a]quinoline-4-carboxaldehyde 2 with substituted thiosemicarbazides, followed by cyclization of the resulting thiosemicarbazones 3 with malonic acid in the presence of acetyl chloride to give pyrimidyl derivatives 4a-c. The second series was prepared by the condensation of the latter compounds 4a-c with the selected aromatic aldehydes to afford the arylidene derivatives 5a-f. The third series 7a-c was synthesized by condensation of tetrazolo[1,5-a]quinoline-4-carboxaldehyde 2 with the appropriate acetophenone, followed by cyclocondensation of the formed alpha,beta-unsaturated ketones with thiourea. The newly synthesized compounds were evaluated for their anti-inflammatory and antimicrobial activities. Four compounds were proved to be as active as indomethacin in animal models of inflammation.
Bekhit
Adnan A
AA
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Alexandria, Alexandria 21215, Egypt. adnbekhit@hotmail.com
El-Sayed
Ola A
OA
Aboulmagd
Elsayed
E
Park
Ji Young
JY
D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry; D002351:Carrageenan / Q000633:toxicity; D015195:Drug Design; D006099:Granuloma / Q000139:chemically induced / Q000188:drug therapy*; D007213:Indomethacin / Q000494:pharmacology; D007249:Inflammation; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D008826:Microbial Sensitivity Tests; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D051381:Rats; D017207:Rats, Sprague-Dawley; D013276:Stomach Ulcer / Q000139:chemically induced / Q000188:drug therapy*; D013329:Structure-Activity Relationship; D023382:Toxicity Tests, Acute
D000890:Anti-Infective Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D011804:Quinolines; D002351:Carrageenan; C037219:quinoline; D007213:Indomethacin