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Photoinduced Generation of Acyl Radicals from Simple Aldehydes, Access to 3-Acyl-4-arylcoumarin Derivatives, and Evaluation of Their Antiandrogenic Activities

Author:
Kawaai, Kazuki, Yamaguchi, Tomoaki, Yamaguchi, Eiji, Endo, Satoshi, Tada, Norihiro, Ikari, Akira, Itoh, Akichika
Source:
Journal of organic chemistry 2018 v.83 no.4 pp. 1988-1996
ISSN:
1520-6904
Subject:
aldehydes, catalysts, cell proliferation, chemical structure, coumarin, cyclization reactions, free radicals, hydrogen, organic chemistry, photocatalysis, prostate-specific antigen, secretion
Abstract:
A novel photocatalysis to construct the 3-acyl-4-arylcoumarin framework from simple aldehyde with ynoate is described. The reaction proceeded through an acyl radical intermediate generated by hydrogen atom abstraction from aldehyde, followed by reaction with ynoate and then cyclization to afford coumarins. This valuable radical cyclization reaction gave over 20 coumarin derivatives in moderate to good yields with inexpensive 2-ᵗBu-anthraquinone as a catalyst. In addition, synthetic coumarins were investigated for 5α-dihydrotestosterone (DHT)-induced secretion of prostate-specific antigen (PSA) levels and cell proliferation of androgen-dependent CWR22Rv1 cells.
Agid:
6046817