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Treatment of 3-cyanoacetyl indole
1 with the diazonium salts of 3-phenyl-5-aminopyrazole and 2-aminobenzimidazole afforded the corresponding hydrazones
4 and
5. 3-Cyanoacetyl indole reacted with phenylisothiocyanate to give the corresponding thioacetanilide derivative
7. Treatment of
7 with hydrazonoyl chlorides afforded the corresponding 1,3,4-thiadiazole derivatives
8a–
f and
9. Also, the thioacetanilide reacted with α-haloketones to afford thiophene derivatives
10a,
b (tenidap analogues), or thiazolidin-4-one derivative
11. The newly synthesized compounds were found to possess potential anti-inflammatory and analgesic activities.