苯并呋喃的卤素及芳基-/杂芳基哌嗪基衍生物的合成与细胞毒性特性
Synthesis and cytotoxic properties of halogen and aryl-/heteroarylpiperazinyl derivatives of benzofurans.
作者信息
Krawiecka Mariola, Kuran Bozena, Kossakowski Jerzy, Cieslak Marcin, Kazmierczak-Baranska Julia, Krolewska Karolina, Nawrot Barbara
机构信息
Chair and Department of Biochemistry, Medical University of Warsaw, 1 Banacha Str., 02-097 Warsaw, Poland.
出版信息
Anticancer Agents Med Chem. 2015;15(1):115-21. doi: 10.2174/187152061501141204124709.
A series of seven derivatives of 1,1'-(5,6-dimethoxy-3-methyl-1-benzofuran-2,7-diyl)diethanone was synthesized and characterized by (1)HNMR and ESI MS spectra and elemental analyses. The obtained new compounds and three halogen derivatives of benzofuran, reported in our earlier work, were tested for their cytotoxic properties in human chronic (K562) and acute (HL60) leukemia cells, human cervical cancer (HeLa), and normal endothelial cells (HUVEC). Four compounds (2, 3, 4, 5), which contain halogens in their structure showed significant anticancer activity. The most promising was 1,1'-[3- (bromomethyl)-5,6-dimethoxy-1-benzofuran-2,7-diyl]diethanone (2), which was highly and selectively toxic for K562 cells (IC50 of 5µM) and HL60 cells (IC50 of 0.1µM), which showed no cytotoxicity toward HeLa and HUVEC cells. Moreover, the observed remarkable cytotoxicity of this compound toward K562 cells resulted from cells apoptosis.
合成了一系列七个1,1'-(5,6-二甲氧基-3-甲基-1-苯并呋喃-2,7-二基)二乙酮衍生物，并通过¹H NMR、ESI MS光谱和元素分析对其进行了表征。将所获得的新化合物以及我们早期工作中报道的三种苯并呋喃卤素衍生物，针对其在人慢性（K562）和急性（HL60）白血病细胞、人宫颈癌（HeLa）和正常内皮细胞（HUVEC）中的细胞毒性特性进行了测试。四种在其结构中含有卤素的化合物（2、3、4、5）显示出显著的抗癌活性。最有前景的是1,1'-[3-(溴甲基)-5,6-二甲氧基-1-苯并呋喃-2,7-二基]二乙酮（2），它对K562细胞（IC50为5μM）和HL60细胞（IC50为0.1μM）具有高度且选择性的毒性，对HeLa和HUVEC细胞无细胞毒性。此外，观察到该化合物对K562细胞具有显著的细胞毒性是由细胞凋亡引起的。
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