1,2,3-Triazole-, arylamino- and thio-substituted 1,4-naphthoquinones: Potent antitumor activity, electrochemical aspects, and bioisosteric replacement of C-ring-modified lapachones
1,2,3-Triazole-, arylamino- and thio-substituted 1,4-naphthoquinones: Potent antitumor activity, electrochemical aspects, and bioisosteric replacement of C-ring-modified lapachones
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DOI：
10.1016/j.bmc.2014.01.033
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发表时间：
2014-03-01
影响因子：
3.5
通讯作者：
da Silva Junior, Eufranio N.
中科院分区：
文献类型：
--
作者：
da Cruz, Eduardo H. G.;Hussene, Caio M. B.;da Silva Junior, Eufranio N.
以中等产率合成了1，2，3-三唑-、芳氨基-和硫代萘醌（分别为24、8和2个代表），并对几种人癌细胞系（血液、卵巢、乳腺、中枢神经系统、结肠和前列腺癌以及黑色素瘤）进行了评价，显示其中一些化合物的IC 50值低于2 μ M。还在非肿瘤细胞如人外周血单核细胞（PBMC）和两种鼠成纤维细胞系（L929和V79细胞）上测定了测试的萘醌的细胞毒性潜力。基于α-拉帕酮和去甲-α-拉帕酮的1，2，3-三唑和芳氨基取代的萘醌显示出对不同癌细胞系的有效细胞毒性。这些化合物可能是抗癌药物开发的有前途的新的铅衍生物。选择的化合物的电化学性质进行了评价，试图将它们与抗肿瘤活性。(C)2014爱思唯尔有限公司版权所有。
1,2,3-Triazole-, arylamino- and thio-substituted naphthoquinones (24, 8, and 2 representatives, respectively) were synthesized in moderate yields and evaluated against several human cancer cell lines (blood, ovarian, breast, central nervous system, colon, and prostate cancers and melanoma), showing, for some of them, IC50 values below 2 mu M. The cytotoxic potential of the tested naphthoquinones was also assayed on non-tumor cells such as human peripheral blood mononucluear cells (PBMC) and two murine fibroblast lines (L929 and V79 cells). alpha-Lapachone-and nor-alpha-lapachone-based 1,2,3-triazoles and arylamino-substituted naphthoquinones showed potent cytotoxicity against different cancer cell lines. The compounds may represent promising new lead derivatives for anticancer drug development. The electrochemical properties of selected compounds were evaluated in an attempt to correlate them with antitumor activity. (C) 2014 Elsevier Ltd. All rights reserved.