Synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities

A series of 6,8-diiodocoumarin-3-N-carboxamides (4–11) were prepared. Treatment of ethyl 6,8-diiodocoumarin-3-carboxylate (1) with ethyl cyanoacetate/NH(4)OAc 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-carbonitril...

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Autores principales: Mohamed, Hany M, EL-Wahab, Ashraf H F Abd, EL-Agrody, Ahmed M, Bedair, Ahmed H, Eid, Fathy A, Khafagy, Mostafa M, Abd-EL-Rehem, Kamal A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3252874/
https://www.ncbi.nlm.nih.gov/pubmed/22238548
http://dx.doi.org/10.3762/bjoc.7.199
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author Mohamed, Hany M
EL-Wahab, Ashraf H F Abd
EL-Agrody, Ahmed M
Bedair, Ahmed H
Eid, Fathy A
Khafagy, Mostafa M
Abd-EL-Rehem, Kamal A
author_facet Mohamed, Hany M
EL-Wahab, Ashraf H F Abd
EL-Agrody, Ahmed M
Bedair, Ahmed H
Eid, Fathy A
Khafagy, Mostafa M
Abd-EL-Rehem, Kamal A
author_sort Mohamed, Hany M
collection PubMed
description A series of 6,8-diiodocoumarin-3-N-carboxamides (4–11) were prepared. Treatment of ethyl 6,8-diiodocoumarin-3-carboxylate (1) with ethyl cyanoacetate/NH(4)OAc 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 NH(4)OAc 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 12–14a,b exhibited a pronounced effect on all tested microorganisms.
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spelling pubmed-32528742012-01-11 Synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities Mohamed, Hany M EL-Wahab, Ashraf H F Abd EL-Agrody, Ahmed M Bedair, Ahmed H Eid, Fathy A Khafagy, Mostafa M Abd-EL-Rehem, Kamal A Beilstein J Org Chem Full Research Paper A series of 6,8-diiodocoumarin-3-N-carboxamides (4–11) were prepared. Treatment of ethyl 6,8-diiodocoumarin-3-carboxylate (1) with ethyl cyanoacetate/NH(4)OAc 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 NH(4)OAc 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 12–14a,b exhibited a pronounced effect on all tested microorganisms. Beilstein-Institut 2011-12-19 /pmc/articles/PMC3252874/ /pubmed/22238548 http://dx.doi.org/10.3762/bjoc.7.199 Text en Copyright © 2011, Mohamed et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Mohamed, Hany M
EL-Wahab, Ashraf H F Abd
EL-Agrody, Ahmed M
Bedair, Ahmed H
Eid, Fathy A
Khafagy, Mostafa M
Abd-EL-Rehem, Kamal A
Synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities
title Synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities
title_full Synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities
title_fullStr Synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities
title_full_unstemmed Synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities
title_short Synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities
title_sort synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3252874/
https://www.ncbi.nlm.nih.gov/pubmed/22238548
http://dx.doi.org/10.3762/bjoc.7.199
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