Synthesis of raloxifene-like quinoxaline derivatives by intramolecular electrophilic cyclization with disulfides

Bioorg Med Chem Lett. 2023 Jul 31:129415. doi: 10.1016/j.bmcl.2023.129415. Online ahead of print.ABSTRACTThe 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.PMID:37532107 | DOI:10.1016/j.bmcl.2023.129415
Source: Bioorganic and Medicinal Chemistry Letters - Category: Chemistry Authors: Source Type: research