| Literature DB >> 26889756 |
Mykhaylo S Frasinyuk1,2,3, Galyna P Mrug4, Svitlana P Bondarenko5, Volodymyr P Khilya5, Vitaliy M Sviripa6,7, Oleksandr A Syrotchuk8, Wen Zhang6,9, Xianfeng Cai6,9, Michael V Fiandalo10, James L Mohler10, Chunming Liu6,9, David S Watt11,12,13.
Abstract
The regioselective condensations of various 7-hydroxyisoflavonoids with bis(N,N-dimethylamino)methane in a Mannich reaction provided C-8 N,N-dimethylaminomethyl-substituted isoflavonoids in good yield. Similar condensations of 7-hydroxy-8-methylisoflavonoids led to the C-6-substituted analogs. Thermal eliminations of dimethylamine from these C-6 or C-8 N,N-dimethylaminomethyl-substituted isoflavonoids generated ortho-quinone methide intermediates within isoflavonoid frameworks for the first time. Despite other potential competing outcomes, these ortho-quinone methide intermediates trapped dienophiles including 2,3-dihydrofuran, 3,4-dihydro-2H-pyran, 3-(N,N-dimethylamino)-5,5-dimethyl-2-cyclohexen-1-one, 1-morpholinocyclopentene, and 1-morpholinocyclohexene to give various inverse electron-demand Diels-Alder adducts. Several adducts derived from 8-N,N-dimethylaminomethyl-substituted isoflavonoids displayed good activity in the 1-10 μm concentration range in an in vitro proliferation assay using the PC-3 prostate cancer cell line.Entities:
Keywords: Mannich reactions; inverse electron-demand Diels-Alder reaction; isoflavonoids; ortho-quinone methides; prostate cancer PC-3 cell line
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Year: 2016 PMID： 26889756 PMCID： PMC4818953 DOI： 10.1002/cmdc.201600008
Source DB: PubMed Journal: ChemMedChem ISSN： 1860-7179 Impact factor: 3.466