Design, Synthesis and Biological Evaluation of Novel Pyrano[2,3-c]pyrazoles And Their Sugar Derivatives as Antimicrobial, Antioxidant and Anticancer Agents | ||
| Egyptian Journal of Chemistry | ||
| Volume 65, Issue 132, December 2022, Pages 1489-1505 PDF (1.52 M) | ||
| Document Type: Original Article | ||
| DOI: 10.21608/ejchem.2022.143253.6253 | ||
| Authors | ||
| Ibrahim F. Fathy Nassar* 1; hadeer el feky2; zeinab khaaled Hamza3; Heba Abo-Salem4; Adel A.-H. Abdel-Rahman5 | ||
| 1365 شارع رمسيس العباسية | ||
| 2chemistry dept. faculty of science, menofua univsersity | ||
| 3national research center | ||
| 4Chemistry of Natural Compounds Department, National Research Centre, P.O. Box 12622 Dokki, Giza, Egypt | ||
| 5Chemistry Department, Faculty of Science, Menoufia University, Shebin El-Koam, EGYPT. | ||
| 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. | ||
| Keywords | ||
| Pyranopyrazole; Antimicrobial; Antioxidant; Anticancer; Docking | ||
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