Study of the Biological Activity of Microwave Synthesized of some new Pyridine derivatives fused with Sulfonamide Moiety | ||
| Egyptian Journal of Chemistry | ||
| Volume 66, Issue 13, December 2023, Pages 1779-1790 PDF (314.42 K) | ||
| Document Type: Original Article | ||
| DOI: 10.21608/ejchem.2023.245709.8801 | ||
| Authors | ||
| Islam Ragab* 1; Rasha Abd El-Hady2 | ||
| 1Department of Mathematics, College of Science and Arts, Qassim University, Riyadh Al Khabra, Saudi Arabia | ||
| 2Department of chemistry, Faculty of science, Jazan university, Saudi Arabia. | ||
| Abstract | ||
| Alkylation of pyridine 1a,b with 3-chloropropanol, 1,3-dichloroisopropanol, epichlorohydrin and methyl bromoacetate under microwave irradiation afforded N-(4-(5-cyano-6-(3-hydroxypropoxy)-4-(4-isopropylphenyl)pyridin-2-yl)phenyl)-4-methylbenzenesulfonamide (2a), N-(4-(5-cyano-6-(3-hydroxypropoxy)-4-(thiophen-2-yl)pyridin-2-yl)phenyl)-4-methylbenzenesulfonamide (2b), N-(4-(6-(3-chloro-2-hydroxypropoxy)-5-cyano-4-(4-isopropylphenyl)-pyridin-2-yl)phenyl)-4-methylbenzenesulfonamide (3a), N-(4-(6-(3-chloro-2-hydroxypropoxy)-5-cyano-4-(thiophen-2-yl)pyridin-2-yl)phenyl)-4-methylbenzenesulfonamide (3b), N-(4-(5-cyano-4-(4-isopropylphenyl)-6-(oxiran-2-ylmethoxy)pyridin-2-yl)phenyl)-4-methylbenzenesulfonamide (4a), N-(4-(5-cyano-6-(oxiran-2-ylmethoxy)-4-(thiophen-2-yl)pyridin-2-yl)phenyl)-4-methylbenzenesulfonamide (4b), Methyl 2-(3-cyano-4-(4-isopropylphenyl)-6-(4-(4-methylphenylsulfon-amido)-phenyl)pyridin-2-yloxy)acetate (5a), Methyl 2-(3-cyano-6-(4-(4-methylphenylsulfonamido)phenyl)-4-(thiophen-2-yl)pyridin-2-yloxy)acetate (5b) respectively. Hydrazenolysis of pyridine 5a,b with hydrazine hydrate afforded N-(4-(5-cyano-6-(2-hydrazinyl-2-oxoethoxy)-4-(4-isopropylphenyl)-pyridin-2-yl)phenyl)-4-methylbenzenesulfonamide (6a) and N-(4-(5-cyano-6-(2-hydrazinyl-2-oxoethoxy)-4-(thiophene-2-yl)-pyridin-2-yl)phenyl)-4-methylbenzenesulfonamide (6b). Reaction of pyridine 1a,b with methyl bromide derivatives 7 resulted in 2-((3-Cyano-4-(4-isopropylphenyl)-6-(4-(4-methylphenylsulfon-amido)phenyl)-2-oxopyridin-1(2H)-yl)methoxy)ethyl acetate (8a) and 2-((3-Cyano-6-(4-(4-methylphenylsulfonamido)phenyl)-4-(thiophen-2-yl)pyridin-2-yloxy)methoxy)ethyl acetate (10b), respectively, while reaction of pyridine 1a,b with 4-bromobutyl acetate 12 yielded 4-(3-Cyano-4-(4-isopropylphenyl)-6-(4-(4-methylphenylsulfonamido)-phenyl)pyridin-2-yloxy)butyl acetate (13a) and 4-(3-Cyano-6-(4-(4-methylphenylsulfonamido)phenyl)-4-(thiophen-2-yl)pyridin-2-yloxy)butyl acetate (13b). Deacetylation of pyridine 8a, 10b and 13a,b afforded N-(4-(5-cyano-1-((2-hydroxyethoxy)methyl)-4-(4-isopropylphenyl)-6-oxo-1,6-dihydropyridin-2-yl)phenyl)-4-methylbenzenesulfonamide (9a), N-(4-(5-cyano-6-((2-hydroxyethoxy)methoxy)-4-(thiophene-2-yl)-pyridin-2-yl)phenyl)-4-methylbenzenesulfonamide (11b), N-(4-(5-cyano-6-(4-hydroxybutoxy)-4-(4-isopropylphenyl)pyridin-2-yl)-phenyl)-4-methylbenzenesulfonamide (14a) and N-(4-(5-cyano-6-(4-hydroxybutoxy)-4-(thiophene-2-yl)pyridin-2-yl)phenyl)-4-methylbenzenesulfonamide (14b).. pyridine 1a,b was reacted with allyl bromide to gave a mixture of N-(4-(6-(allyloxy)-5-cyano-4-(4-isopropylphenyl)pyridin-2-yl)phenyl)-4-methylbenzenesulfonamide (15a), N-(4-(6-(allyloxy)-5-cyano-4-(thiophen-2-yl)pyridin-2-yl)phenyl)-4-methylbenzenesulfonamide (15b), N-(4-(1-allyl-5-cyano-4-(4-isopropylphenyl)-6-oxo-1,6-dihydropyridin-2-yl)phenyl)-4-methylbenzenesulfonamide (16a) and N-(4-(1-allyl-5-cyano-6-oxo-4-(thiophen-2-yl)-1,6-dihydropyridin-2-yl)phenyl)-4-methylbenzenesulfonamide (16b).while alkylation with propargyl bromide gave a mixture of N-(4-(5-cyano-4-(4-isopropylphenyl)-6-(prop-2-ynyloxy)pyridin-2-yl)phenyl)-4-methylbenzenesulfonamide (17a), N-(4-(5-cyano-6-(prop-2-ynyloxy)-4-(thiophen-2-yl)pyridin-2-yl)phenyl)-4-methylbenzenesulfonamide (17b), N-(4-(5-cyano-4-(4-isopropylphenyl)-6-oxo-1-(prop-2-ynyl)-1,6-dihydro-pyridin-2-yl)phenyl)-4-methylbenzenesulfonamide (18a) and N-(4-(5-cyano-6-oxo-1-(prop-2-ynyl)-4-(thiophen-2-yl)-1,6-dihydro-pyridin-2-yl)phenyl)-4-methylbenzenesulfonamide (18b). .Antitumor activity and cytotoxicity of the pyridine 4a, 4b, 13a, 15b and 17b were evaluated. Additionally, the antimicrobial activity of pyridine 2a, 3a, 4b, 15a and 18b were evaluated. | ||
| Keywords | ||
| Synthesis, Microwave; Sulfonamide pyridine; Antimicrobial activity; Cytotoxicity | ||
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