用二硫化物进行分子内亲电环化合成雷洛昔芬类似物喹喔啉衍生物。
Synthesis of raloxifene-like quinoxaline derivatives by intramolecular electrophilic cyclization with disulfides.
机构信息
Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan.
Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan; Division of Instrumental Analysis, Life Science Research Center, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan.
出版信息
Bioorg Med Chem Lett. 2023 Sep 1;93:129415. doi: 10.1016/j.bmcl.2023.129415. Epub 2023 Aug 1.
The intramolecular electrophilic cyclization of alkynes with disulfides to form thieno[2,3-b]quinoxaline structures and to introduce thioether substituents afforded quinoxaline derivatives (7a-7d, 8a-8d). Among obtained eight derivatives, the raloxifene analogues (7c, 8b) showed specifically high cytotoxicity against breast cancer cells (SK-BR-3), and raloxifene analogues (8a) showed the highest cytotoxicity against human leukemia cells (HL-60). None of the raloxifene analogues (7a-7d, 8a-8d) showed cytotoxicity against human lung fibroblasts (WI-38), which are normal cells.
炔烃与二硫化物的分子内亲电环化反应形成噻吩[2,3-b]喹喔啉结构并引入硫醚取代基，得到喹喔啉衍生物（7a-7d、8a-8d）。在所得到的八个衍生物中，雷洛昔芬类似物（7c、8b）对乳腺癌细胞（SK-BR-3）表现出特别高的细胞毒性，而雷洛昔芬类似物（8a）对人白血病细胞（HL-60）表现出最高的细胞毒性。雷洛昔芬类似物（7a-7d、8a-8d）对正常细胞人肺成纤维细胞（WI-38）均无细胞毒性。
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