2-(2'-氟苯基)-4-??酮-8-乙酸衍生物之合成及生物活性; Synthesis and Biological activity of 2-(2'-Fluorophenyl)-4-quinolone-8-acetic acid Derivatives

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Title:	2-(2'-氟苯基)-4-??酮-8-乙酸衍生物之合成及生物活性;Synthesis and Biological activity of 2-(2'-Fluorophenyl)-4-quinolone-8-acetic acid Derivatives
Authors:	陳建廷;Chen Chien Ting
Contributors:	中國醫藥大學藥物化學研究所
Keywords:	??酮;2-hpenyl-4-quinolone-8-acetic acid
Date:	2004
Issue Date:	2010-01-20 16:55:42 (UTC+8)
Abstract:	中文摘要過去合成出2-(2'-fluorophenyl)-4-quinolone-8-acetic acid並評估其細胞致毒活性，結果顯示具有明顯的活性，由於此項初步結果，因而從事2-(2'-fluorophenyl)-4-quinolone-8-acetic acid之類緣化合物之合成。首先將substituted acetophenone 1-6和diethylcarbonate反應得到substituted ethyl benzoylacetates 8-13；另將2-nitrophenylacetic acid 14與甲醇經由酯化反應得到 ester 15。爾後將化合物15進行還原反應形成化合物16，接著再與化合物8-13反應生成methyl 2-(substituted phenyl) -4-quinolone-8-acetates 17-23，最後水解化合物17-23而得到化合物2-(Substituted phenyl)-4-quinolone-8-acetic acids 24-30。另取化合物26進行縮合反應形成化合物31，再與N,N-dimethylethylendiamine反應生成amide衍生物32。檢視化合物24之動物試驗與化合物24-30之細胞致毒活性與基因活性之篩選，結果顯示化合物24在BMP4, CSF1, CTGF, IL17E, KITLG等基因上具有明顯活化之作用。; Abstract In the present study, 2-(2'-fluorophenyl)-4-quinolone-8-acetic acid was synthesized and cytotoxicity was evaluated. The result showed significant activity. Encouraged by the initial result, 2-(2'-fluorophenyl) -4-quinolone-8-acetic acid derivatives were synthesized。 Reaction of substituted acetophenones 1-6 with diethylcarbonate yielded the substituted ethyl benzoylacetates 8-13. Esterification of 2-nitrophenylacetic acid 14 with methanol got the compound 15. Then, reduction of comupound 15 got the compound 16 that reacted with compounds 8-13 via cyclization to get methyl 2-(substituted phenyl) -4-quinolone-8-acetates 17-23. Finally, hydrolysis of compound 17-23 gained 2-(substituted phenyl)-4-quinolone-8-acetic acids 24-30. Select the compound 26 that condensated to compound 31, then reaction with N,N-dimethylethylendiamine to form amide derivative 32。 Compound 24 was examined for animal test, and compound 24-30 were screened activity of cytotoxicity and microarray. The result showed significant activity of microarray for the compound 24 on the BMP4, CSF1, CTGF, IL17E, KITLG .
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