2,5-双（烷氨基）-1,4-苯醌的合成与生物评价。

Synthesis and biological evaluation of 2,5-bis(alkylamino)-1,4-benzoquinones.

机构信息

Department of Chemistry, Federal University of Viçosa. Av. P.H. Rolfs, Viçosa, MG, Brazil.

出版信息

Molecules. 2010 Aug 13;15(8):5629-43. doi: 10.3390/molecules15085629.

DOI:10.3390/molecules15085629

PMID:20714317

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6257688/

Abstract

A series of twelve 2,5-bis(alkylamino)-1,4-benzoquinones were prepared in yields ranging from 9-58% via the reaction between p-benzoquinone and various amines. The structures of the synthesized compounds were confirmed by IR, 1H- and 13C-NMR and MS analyses. The phytotoxicity of the 2,5-bis(alkylamino)-1,4-benzoquinones was evaluated against two crop species, Cucumis sativus and Sorgum bicolor, at 1.0 x 10(-3) mol/L. In general, the quinones displayed inhibitory effects on the dicotyledonous species C. sativus (7-74%). On the other hand stimulatory effects were observed on S. bicolor (monocotyledonous). Similar results were observed in the biological assays carried out with the weed species Ipomoea grandifolia (dicotyledonous) and Brachiaria decumbens (monocotyledonous). In addition, the cytotoxicity of the 2,5-bis(alkylamino)-1,4-benzoquinones was assayed against HL-60 (leukemia), MDA-MB-435 (melanoma), SF-295 (brain) and HCT-8 (colon) human cancer cell lines and human peripheral blood mononuclear cells (PBMC), as representatives of healthy cells, using a MTT and an Alamar Blue assay. Compound 12 was the most active, displaying cytotoxicity against all cancer cell lines tested.

摘要

通过 p-苯醌与各种胺之间的反应，制备了一系列产率为 9-58%的十二种 2,5-双（烷基氨基）-1,4-苯醌。通过 IR、1H-和 13C-NMR 和 MS 分析确认了合成化合物的结构。在 1.0 x 10(-3)mol/L 下，评估了 2,5-双（烷基氨基）-1,4-苯醌对两种作物（黄瓜和高粱）的植物毒性。一般来说，醌类对双子叶植物 C. sativus（7-74%）表现出抑制作用。另一方面，在高粱（单子叶植物）上观察到刺激作用。在对杂草物种大花牵牛（双子叶植物）和马唐（单子叶植物）进行的生物测定中也观察到了类似的结果。此外，使用 MTT 和 Alamar Blue 测定法，以 HL-60（白血病）、MDA-MB-435（黑色素瘤）、SF-295（脑）和 HCT-8（结肠）人癌细胞系和人外周血单核细胞（PBMC）作为健康细胞的代表，对 2,5-双（烷基氨基）-1,4-苯醌的细胞毒性进行了测定。化合物 12 是最活跃的，对所有测试的癌细胞系均显示出细胞毒性。