2-[氮-取代芐基-4´(或3´)-溴基]苯胺基-4-酮基-4, 5-二氫呋喃-3-羧酸乙酯之合成及其生理活性; Synthesis and Biological Activity of Ethyl 2-[N-substituted benzyl-4¢(or 3¢)-bromo]anilino-4-oxo-4,5-dihydro- furan-3-carboxylate

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题名:	2-[氮-取代芐基-4´(或3´)-溴基]苯胺基-4-酮基-4, 5-二氫呋喃-3-羧酸乙酯之合成及其生理活性;Synthesis and Biological Activity of Ethyl 2-[N-substituted benzyl-4¢(or 3¢)-bromo]anilino-4-oxo-4,5-dihydro- furan-3-carboxylate
作者:	蘇怡芳;I -Fang Su
贡献者:	中國醫藥大學：藥物化學研究所碩士班
关键词:	取代芐基;苯胺基;4, 5-二氫呋;喃;N-substituted;anilino;dihydrofuran
日期:	2006-06-22
上传时间:	2009-08-13 09:37:18 (UTC+8)
摘要:	著者合成了一系列2-[氮-取代芐基-4´(或3´)-溴基]苯胺基-4-酮基-4, 5-二氫呋喃-3-羧酸乙酯化合物，且經各種圖譜資料予以確認之後，將所有合成經結構判定正確之化合物分別測試其抗心律不整與抗血管收縮活性。在心律測試方面，化合物Ethyl 2-[N-m-fluorobenzyl-(3´-bromo)] anilino-4-oxo-4,5-dihydrofuran-3-carboxylate（27）、Ethyl 2-[N-m-chloro- benzyl-(3´-bromo)]anilino-4-oxo-4,5-dihydrofuran-3-carboxylate（30）、Ethyl 2-[N- benzyl-(3´-bromo)]anilino-4-oxo-4,5-dihydrofuran-3- carboxylate（19）在30μM抑制活性最強；化合物Ethyl 2-[N-benzyl- (4´-bromo)]anilino-4-oxo-4,5dihydrofuran-3-carboxylate（2），Ethyl 2-[N-m-methylbenzyl-(4´-bromo)]anilino-4-oxo-4,5-dihydrofuran-3- carboxylate（4），Ethyl 2-[N-m-fluorobenzyl-(4´-bromo)]anilino-4-oxo- 4,5-dihydrofuran-3-carboxylate（10），Ethyl 2-[N-m-chlorobenzyl-(4´- bromo)]anilino-4-oxo-4,5-dihydrofuran-3-carboxylate（13），Ethyl 2-[N- o-nitrobenzyl-(4´-bromo)]anilino-4-oxo-4,5-dihydrofuran-3-carboxylate （15），Ethyl 2-[N-p-nitrobenzyl-(4´-bromo)]anilino-4-oxo-4,5-dihydro- furan-3-carboxylate（17），Ethyl 2-[N-o-methylbenzyl-(3´-bromo)] anilino-4-oxo-4,5-dihydrofuran-3-carboxylate（20），Ethyl 2-[N-p- chlorobenzyl-(3´-bromo)]anilino-4-oxo-4,5-dihydrofuran-3-carboxylate （31），Ethyl 2-[N-o-nitrobenzyl-(3´-bromo)]anilino-4-oxo-4,5-dihydro- furan-3-carboxylate（32）呈現較佳之抑制活性，且不會抑制右心房自發性節律；而Ethyl 2-[N-m-methyl benzyl-(3´-bromo)]anilino-4-oxo-4,5- dihydrofuran-3-carboxylate（21）和Ethyl 2-[N-p-methoxybenzyl-(3´- bromo)]anilino-4-oxo-4,5-dihydrofuran-3-carboxylate（24）在10μM也具較好之抑制活性，但在30μM卻會抑制右心房自發性節律。而在強心測試方面，化合物Ethyl 2-[N-m-methylbenzyl-(4´-bromo)] anilino-4-oxo-4,5-dihydrofuran-3-carboxylate（4），Ethyl 2-[N-m-methoxy benzyl-(4´-bromo)]anilino-4-oxo-4,5-dihydrofuran-3-carboxylate（7）， Ethyl 2-[N-p-methoxybenzyl-(4´-bromo)]anilino-4-oxo-4,5-dihydrofuran- 3-carboxylate（8），Ethyl 2-[N-m- fluorobenzyl-(4´-bromo)]anilino-4-oxo- 4,5-dihydrofuran-3-carboxylate（10）與Ethyl 2-[N-p- methoxybenzyl-(3´- bromo)]anilino-4-oxo-4,5-dihydrofuran-3-carboxylate（25）在強心方面有較好之藥理活性。總結，本系列化合物基本上大部份皆具有增加心收縮力與減慢心跳頻律作用。 A series of ethyl 2-[N-substituted benzyl- 4´(or 3´)-bromo]anilino- 4-oxo-4,5-dihydrofuran-3-carboxylate and related compounds has been synthesized and assigned by their spectra data. All of these synthetic compounds were evaluated for anti-arrhythmics activity and cardiovascular effect. Among the investigations of the inhibitory effect on the heart rate , Ethyl 2-[N-m-fluorobenzyl-(3´-bromo)]anilino-4-oxo-4,5-dihydrofuran-3-carboxylate （27）、Ethyl 2-[N-m-chlorobenzyl-(3´-bromo)]anilino-4-oxo-4,5-dihydro- furan-3-carboxylate（30）、Ethyl 2-[N- benzyl-(3´-bromo)]anilino-4-oxo- 4,5-dihydrofuran-3-carboxylate（19）were found to exhibit the most significant activities at 30 μM while pacermaker S.A. node. Ethyl 2-[N- benzyl-(4´-bromo)] anilino-4-oxo-4,5-dihydrofuran-3-carboxylate（2），Ethyl 2-[N-m-methylbenzyl-(4´-bromo)]anilino-4-oxo-4,5-dihydrofuran- 3-carboxylate（4），Ethyl 2-[N-m-fluorobenzyl-(4´-bromo)]anilino-4-oxo- 4,5-dihydrofuran-3-carboxylate（10），Ethyl 2-[N-m-chlorobenzyl-(4´- bromo)]anilino-4-oxo-4,5-dihydrofuran-3-carboxylate（13），Ethyl 2-[N-o-nitrobenzyl-(4´-bromo)]anilino-4-oxo-4,5-dihydrofuran-3- carboxylate（15），Ethyl 2-[N-p-nitrobenzyl-(4´-bromo)]anilino-4-oxo- 4,5-dihydrofuran-3-carboxylate（17），Ethyl 2-[N-o-methylbenzyl- (3´-bromo)]anilino-4-oxo-4,5-dihydrofuran-3-carboxylate（20），Ethyl 2-[N-p-chlorobenzyl-(3´-bromo)]anilino-4-oxo-4,5-dihydrofuran-3- carboxylate（31），Ethyl 2-[N-o-nitrobenzyl-(3´-bromo)]anilino-4-oxo-4,5- dihydrofuran-3-carboxylate（32）exhibited better activities and no inhibitory effect on the pacemaker S.A. node. Ethyl 2-[N-m-methyl benzyl-(3´-bromo)]anilino-4-oxo-4,5-dihydrofuran-3-carboxylate（21） and Ethyl 2-[N-p-methoxybenzyl-(3´-bromo)]anilino-4-oxo-4,5-dihydro- furan-3-carboxylate（24）also exhibited a better inhibitory effect at 10μM，but inhibition to pacemaker S.A. node. occurred at concentrations up to 30 μM. Among the results of the contractivity , ethyl 2-[N-m-methylbenzyl- (4´-bromo)]anilino-4-oxo-4,5-dihydrofuran-3-carboxylate（4），Ethyl 2-[N- m-methoxybenzyl-(4´-bromo)]anilino-4-oxo-4,5-dihydrofuran-3-carboxylate （7），Ethyl 2-[N-p-methoxybenzyl-(4´-bromo)]anilino-4-oxo-4,5-dihydro- furan-3-carboxylate（8），Ethyl 2-[N-m- fluorobenzyl-(4´-bromo)]anilino- 4-oxo-4,5-dihydrofuran-3-carboxylate（10）and Ethyl 2-[N-p- methoxyl benzyl-(3´-bromo)]anilino-4-oxo-4,5-dihydrofuran-3-carboxylate（25） exhibited better activities. In conclusion, most of this series of compounds basically exhibited activities of increasing contractility and lowering heart rate.
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