SARS-CoV 3C-Like Protease Inhibitors of some Newly Synthesized Substituted Pyrazoles and Substituted Pyrimidines Based on 1-(3-Aminophenyl)-3-(1H-indol-3-yl)prop-2-en-1-one

A series of several substituted pyrazole and pyrimidine derivatives were synthesized based on 1-(3-aminophenyl)-3-(1H-indol-3-yl)prop-2-en-1-one (3) as starting material, which was obtained from the reaction of 3-indolaldehyde with 3-aminoacetophenone. Treatment of chalcone 3 with hydrazine hydrate or phenylhydrazine gave the corresponding pyrazole derivatives 4 and 5. Cyclization of 3 with hydroxylamine hydrochloride, thiosemicarbazide or hydrazine hydrate/acetic acid afforded the corresponding cyclized products 6-8, respectively. The reaction of 3 with guanidine hydrochloride gave the corresponding aminopyrimidine derivative 9, which was reacted with 1, 1-carbonyldiimidazole or p-flourobenzaldehyde afforded compounds 10 and 11. Condensation of 3 with urea in the presence of sodium ethoxide gave pyrimidinone derivative 12. Finally, reaction of 9 with 1, 3-indanedione afforded compound 13, which was treated with cyclopentanone or 3, 4-dimethoxybenzaldehyde to give the corresponding arylidine derivatives 14 and 15. The synthesized derivatives were tested against SARS CoV 3C-like protease and were founded active.