呋喃[3,2-c]喹啉類衍生物之合成及生物活性之研究

Studies on the Synthesis and Biological Activities of Furo[3,2-c]quinoline Derivatives

蔣浩堂(Hao-Tang Chiang)

指導教授 ： 曾誠齊

高雄醫學大學/生命科學院/醫藥暨應用化學研究所/碩士(2004年)

摘要

從芸香科植物中萃取出喹啉之生物鹼具有抗癌、抗菌、抗濾過性病毒等生物活性。多融合雜環芳香化合物具有一個平面結構，因為這種平面結構能夠嵌入去氧核醣核酸中，以達抑制基因複製的效果，因此我們合成出一系列以?K喃[3,2-c]喹啉為主架構的衍生物，並改變碳4的位置上含有苯胺及脂肪胺類的化合物，以提高藥物對各種不同癌細胞的選擇與專一性。化合物furo[3,2-c]quinolin-4-yl-(3-methoxyphenyl)- amine (51)、3-(furo[3,2-c]quinolin-4-ylamino)phenol (54)、4-(furo[3,2-c]-
quinolin-4-ylamino)phenol (55)、(4-fluorophenyl)furo[3,2-c]quinolin-4yl-
amine (56)對肺癌細胞(NCI-H460)、乳癌細胞(MCF-7)以及中樞神經系統癌細胞(SF-268)有很好的抑制活性。而化合物furo[3,2-c]quinolin-
4-yl-(2-methoxyphenyl)amine (50)、furo[3,2-c]quinolin-4-yl-(4-methoxy-
phenyl)amine (52)、2-(furo[3,2-c]quinolin-4-ylamino)phenol(53)、
(4-chlorophenyl)furo[3,2-c]-quinolin-4-ylamine (57)只對肺癌細胞(NCI-H460)有較好的選擇性抑制，將來可以針對不同的癌細胞，依照此結果而在結構上作修飾，以達最佳化的抑制。

關鍵字

?喃[3 ； 2-c]??

並列摘要

The quinoline alkaloids isolated from the Rutaceac family of plants have various biological activities such as anticancer, antibacterial and antiviral effects. Polycondensed heterocyclic aromatic compounds having a planar structure can intercalate into DNA to inhibit the replication. We have synthesized the derivatives of furoquinoline by changing the substitutent at C4, such as aniline group and aliphatic amines, to improve the selectivity and specificity of the compounds against the growth of various cancer cells. The furo[3,2-c]quinolin-4-yl-(3-methoxyphenyl)amine (51), 3-(furo[3,2-c]quinolin-4-ylamino)phenol (54), 4-(furo[3,2-c]quinolin-4-
ylamino)phenol (55) and (4-fluorophenyl)furo[3,2-c]quinolin-4-ylamine
(56) exhibit good inhibition on the lung cancer cell NCI-H460, breast cancer cell MCF-7 and CNS cancer cell SF-268. However, the furo[3,2-c]quinolin-4-yl-(2-methoxyphenyl)amine (50), furo[3,2-c]quino-
lin-4-yl-(4-methoxyphenyl)amine (52), 2-(furo[3,2-c]quinolin-4-ylamino) phenol (53), (4-chlorophenyl)furo[3,2-c]quinolin-4-ylamine (57) demonstrate good inhibition only on lung cancer cell NCI-H460.

並列關鍵字

Furo[3 ； 2-c]quinoline

參考文獻

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