Design, Synthesis and Biological Evaluation of Novel Pyrano[2,3-c]pyrazoles And Their Sugar Derivatives as Antimicrobial, Antioxidant and Anticancer Agents
Nassar, I., el feky, H., Hamza, Z., Abo-Salem, H., Abdel-Rahman, A. (2022). Design, Synthesis and Biological Evaluation of Novel Pyrano[2,3-c]pyrazoles And Their Sugar Derivatives as Antimicrobial, Antioxidant and Anticancer Agents. EKB Journal Management System, 65(132), 1489-1505. doi: 10.21608/ejchem.2022.143253.6253
Ibrahim F. Fathy Nassar; hadeer el feky; zeinab khaaled Hamza; Heba Abo-Salem; Adel A.-H. Abdel-Rahman. "Design, Synthesis and Biological Evaluation of Novel Pyrano[2,3-c]pyrazoles And Their Sugar Derivatives as Antimicrobial, Antioxidant and Anticancer Agents". EKB Journal Management System, 65, 132, 2022, 1489-1505. doi: 10.21608/ejchem.2022.143253.6253
Nassar, I., el feky, H., Hamza, Z., Abo-Salem, H., Abdel-Rahman, A. (2022). 'Design, Synthesis and Biological Evaluation of Novel Pyrano[2,3-c]pyrazoles And Their Sugar Derivatives as Antimicrobial, Antioxidant and Anticancer Agents', EKB Journal Management System, 65(132), pp. 1489-1505. doi: 10.21608/ejchem.2022.143253.6253
Nassar, I., el feky, H., Hamza, Z., Abo-Salem, H., Abdel-Rahman, A. Design, Synthesis and Biological Evaluation of Novel Pyrano[2,3-c]pyrazoles And Their Sugar Derivatives as Antimicrobial, Antioxidant and Anticancer Agents. EKB Journal Management System, 2022; 65(132): 1489-1505. doi: 10.21608/ejchem.2022.143253.6253

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, Page 1489-1505  XML PDF (1.52 MB)
Document Type: Original Article
DOI: 10.21608/ejchem.2022.143253.6253
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Authors
Ibrahim F. Fathy Nassar email orcid 1; hadeer el feky2; zeinab khaaled Hamzaorcid 3; Heba Abo-Salem4; Adel A.-H. Abdel-Rahmanorcid 5
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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