Photoinduced Generation of Acyl Radicals from Simple Aldehydes, Access to 3-Acyl-4-arylcoumarin Derivatives, and Evaluation of Their Antiandrogenic Activities.
Kazuki KawaaiTomoaki YamaguchiEiji YamaguchiSatoshi EndoNorihiro TadaAkira IkariAkichika ItohPublished in: The Journal of organic chemistry (2018)
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.
Keyphrases
- electron transfer
- fatty acid
- cell proliferation
- prostate cancer
- induced apoptosis
- visible light
- mycobacterium tuberculosis
- molecular dynamics
- structure activity relationship
- high intensity
- diabetic rats
- room temperature
- mass spectrometry
- oxidative stress
- endoplasmic reticulum stress
- reduced graphene oxide
- pi k akt
- carbon dioxide