Design, Synthesis and Biological Evaluation of Novel Pyrano[2,3-c]pyrazoles And Their Sugar Derivatives as Antimicrobial, Antioxidant and Anticancer Agents

Abstract

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.

Facile Synthesis of Pyrazolopyranopyrimidines by Synergism of Ultrasound Irradiation and Biocompatible Inulin Biopolymer as Catalyst

“…[16] Pyrazolopyrano [2,3-d]pyrimidine-diones also consist of amalgamations of fused 4H-pyran derivatives, such as pyranopyrimidines and pyranopyrazoles which are counted as significant building blocks in the pharmaceutical discipline due to their immense biological properties. [17][18][19][20][21][22][23][24] The more prominent effect occurs when two or more heterocyclic units are present in a single molecule. The presence of the above-mentioned heterocyclic compounds in a single skeleton facilitates the combination of different possible biological activities of these molecules (Figure 1).…”

“…Additionally, the pyrazole ring is integral to numerous bioactive species exhibiting activities like antibacterial, [11] anti‐malarial, [12] anti‐viral, [13] anti‐oxidant, [14] anti‐inflammatory, [15] and anticancer agents [16] . Pyrazolopyrano[2,3‐d]pyrimidine‐diones also consist of amalgamations of fused 4H‐pyran derivatives, such as pyranopyrimidines and pyranopyrazoles which are counted as significant building blocks in the pharmaceutical discipline due to their immense biological properties [17–24] …”