Synthesis of some indole derivatives with potential antiinflammatory activity.
2-Methylindole-3-acethydrazide (1) was reacted with arylisothiocyanate to give the corresponding 4-arylthiosemicarbazides 2a-d. Cyclization of the latter gave the corresponding 3-mercapto-5-[3-(2-methylindolyl)methyl]-1,2,4-triazoles 3a-d. Compounds 3a-c reacted with chloroacetic acid to give the corresponding indolyl-1,2,4-triazolythioglycolic acids 4a-c. The methylmercapto derivative 5 was also obtained from 3a and methyliodide. The hydrazide 1 was also reacted with carbon disulfide to give the corresponding indolymethyl-1,3,4-oxadiazole-2-thione (6) which was condensed with piperidine and formaldehyde to give the corresponding Mannich base 7. Condensation of 1 with aromatic aldehydes gave the corresponding hydrazones 8a-c which were converted into the corresponding oxadiazolines 9a-c.
D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D008352:Mannich Bases
D000893:Anti-Inflammatory Agents; D007211:Indoles; D008352:Mannich Bases