Synthesis, antibacterial and anticancer studies for new thienopyrazolopyridine and azafluorene derivatives

ABSTRACT

Reaction of thiocyanoacetamide with 3,4,5-trimethoxybenzaldehyde gave the corresponding 2-cyano-3-[3, 4,5-trimethoxyphenyl]- thioacrylamide 1. Reaction of I with ethyl acetoacetate gave the pyridine derivative 2. Cyclization of 2 with hydrazine hydrate gave the pyrazolopyridine derivative 3. Diazotization of 3 gave the diazenyl derivative 4. The latter compound 4 was reacted with malononitrile. acetylacetone and ethyl acetoacetate to give pentoazafluorene derivatives 5-7, respectively. Moreover, the cyclocondensation of compound 2 with ethylchloroacetate, bromoacetophenone, chloroacetamide and chloroacetonitrile gave the thienopyridine jerivatives 8, 11, 12 and 15. Reaction of 12 with formic acid and acetic anhydride gave the thiatriazafluorene derivatives 13 and 14, respectively. Some of the new compounds showed antimicrobial and antifungal activities. Compound 11 has good anticancer activity for liver, breast and colon cancers