Journal
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
Volume 95, Issue 8, Pages 1242-1249Publisher
CHEMICAL SOC JAPAN
DOI: 10.1246/bcsj.20220149
Keywords
Aplaminal; Bioinspired synthesis; Structure-activity relationship
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Funding
- JSPS KAKENHI [JP18H04606, JP20H04764, 20H02865]
- Support for Pioneering Research Initiated by the Next Generation (SPRING)
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The total synthesis of aplaminal with a unique skeleton was achieved, and the effects of different substituents at the para-position on cytotoxicity were investigated.
The total synthesis of aplaminal having a unique triazabicyclo[3.2.1]octane skeleton was accomplished using biomimetic oxidative cyclization as a key reaction. This total synthesis enabled us to prepare aplaminal analogs with a variety of substituents at the para-position in the aromatic ring. We found that an electron-donating group at the para-position enhances cytotoxicity and a hydrogen bond donor at the para-position is suitable for cytotoxicity.
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