Treatment of 2,5-Diphenyl-2,4-dihydro-pyrazol-3-one (1) with 2-Chloro-benzaldehyde (2) in ethanol/sodium hydroxide solution afforded the chalcone derivative (3) which was reacted with malononitrile to afford 6-Amino-4-(2-chloro-phenyl)-1,3-diphenyl-1,4-dihydro-pyrano[2,3-c] pyrazole-5-carbonitrile (4). Compound 4 was reacted with formic acid, acetic anhydride, formamide, thiourea, urea, conc. cold sulfuric acid, D-glucose, p-methoxy benzaldehyde, 4-dimethyl aminobenzaldehyde, benzoyl chloride, triethyl orthoformate to afford a series of pyranopyrazole derivatives (5-15). The formimidic acid ethyl ester 15 was reacted with hydrazine hydrate to afford 4-(2-chlorophenyl)-5-imino-1,3-diphenyl-1,4-dihydropyrazolo[4',3':5,6]pyrano[2,3-d]pyrimidin-6(5H)-amine (16). Compound 16 was then reacted with D-xylose to afford the sugar derivative 17. Also compound 16 was reacted with CS2 to afford 18 in a good yield. Evaluation of the antimicrobial, antioxidant and anticancer Activities of the newly synthesized compounds was performed with a Docking study.