Synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities

Beilstein Journal of Organic Chemistry - Tập 7 - Trang 1688-1696
Hany M. Mohamed1, Ashraf Hassan Fekry Abd El‐Wahab2,3, Ahmed M. El‐Agrody4, Ahmed H. Bedair2, F. Eid2, Mostafa M. Khafagy2, Kamal A Abd-EL-Rehem2
1Chemistry Department, Faculty of Science, Al Azhar University, Nasr City, Cairo, 11884, Egypt
2Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo 11884, Egypt
3Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Saudi Arabia and
4Chemistry Department, Faculty of Science, King Khalid University, 9004 Abha, Saudi Arabia

Tóm tắt

A series of 6,8-diiodocoumarin-3-N-carboxamides (411) were prepared. Treatment of ethyl 6,8-diiodocoumarin-3-carboxylate (1) with ethyl cyanoacetate/NH4OAc gave ethyl 2-(3-carbamoyl-6,8-diiodocoumarin-4-yl)-2-cyanoacetate (12) and 2-amino-4-hydroxy-7,9-diiodocoumarino[3,4-c]pyridine-1-carbonitrile (13), and treatment with acetone in the presence of NH4OAc or methylamine gave the ethyl 4-oxo-2,6-methano-2-methyl-3,4,5,6-tetrahydro-8,10-diiodobenzo[2,1-g]-2H-1,3-oxazocine-5-carboxylate derivatives 14a,b. All compounds were evaluated for their antimicrobial activity and the compounds 1214a,b exhibited a pronounced effect on all tested microorganisms.

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