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新型具有良好抗菌活性的二碘茋衍生物的合成与表征。

Synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities.

机构信息

Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo 11884, Egypt.

出版信息

Beilstein J Org Chem. 2011;7:1688-96. doi: 10.3762/bjoc.7.199. Epub 2011 Dec 19.

DOI:10.3762/bjoc.7.199
PMID:22238548
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3252874/
Abstract

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.

摘要

合成了一系列 6,8-二碘香豆素-3-N-甲酰胺（4-11）。用乙酯 6,8-二碘香豆素-3-羧酸酯（1）与氰基乙酸乙酯/NH(4)OAc 反应，得到乙酯 2-(3-氨基甲酰基-6,8-二碘香豆素-4-基)-2-氰基乙酸酯（12）和 2-氨基-4-羟基-7,9-二碘香豆诺[3,4-c]吡啶-1-甲腈（13），而在 NH(4)OAc 或甲胺存在下用丙酮处理则得到乙酯 4-氧代-2,6-亚甲基-2-甲基-3,4,5,6-四氢-8,10-二碘苯并[2,1-g]-2H-1,3-恶唑嗪-5-羧酸酯衍生物 14a,b。所有化合物都进行了抗菌活性评价，化合物 12-14a,b 对所有测试的微生物都表现出明显的作用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/918a/3252874/00ede350a852/Beilstein_J_Org_Chem-07-1688-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/918a/3252874/622a4e78914e/Beilstein_J_Org_Chem-07-1688-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/918a/3252874/26ca121500ea/Beilstein_J_Org_Chem-07-1688-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/918a/3252874/52a5f8e78eb9/Beilstein_J_Org_Chem-07-1688-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/918a/3252874/4f2878760058/Beilstein_J_Org_Chem-07-1688-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/918a/3252874/765ba54ba632/Beilstein_J_Org_Chem-07-1688-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/918a/3252874/b57a8b6e32e6/Beilstein_J_Org_Chem-07-1688-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/918a/3252874/00ede350a852/Beilstein_J_Org_Chem-07-1688-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/918a/3252874/622a4e78914e/Beilstein_J_Org_Chem-07-1688-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/918a/3252874/26ca121500ea/Beilstein_J_Org_Chem-07-1688-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/918a/3252874/52a5f8e78eb9/Beilstein_J_Org_Chem-07-1688-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/918a/3252874/4f2878760058/Beilstein_J_Org_Chem-07-1688-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/918a/3252874/765ba54ba632/Beilstein_J_Org_Chem-07-1688-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/918a/3252874/b57a8b6e32e6/Beilstein_J_Org_Chem-07-1688-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/918a/3252874/00ede350a852/Beilstein_J_Org_Chem-07-1688-g003.jpg

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