Abstract
Abstract: An efficient method for regioselective synthesis of C-7 Mannich bases of 6-hydroxyaurones was accomplished by the N,N-dialkylaminomethylation using aminals prepared from dimethylamine, dipropylamine, bis(2-methoxyethyl)amine, N-methylbutylamine, N-methylbenzylamine, morpholine, piperidine, and 1-methylpiperazine. Further transformation of 7-(N,N-dialkylamino)methyl group in these aurones led to formation of C-7 acetoxymethyl and methoxymethyl derivatives of 6-hydroxyaurones, some of which showed promising inhibition of PC-3 prostate cancer cell proliferation in the high nanomolar to low micromolar range that exceeded that of cisplatin. Graphical abstract: Compound 12c (R3 = Ac, Ar = 3,4-OMePh) displays 75% inhibition of PC-3 prostate cancer cells proliferation at 300 nM concentration.[Figure not available: see fulltext.]
Original language | English |
---|---|
Pages (from-to) | 2443-2456 |
Number of pages | 14 |
Journal | Chemical Papers |
Volume | 72 |
Issue number | 10 |
DOIs | |
State | Published - Oct 1 2018 |
Bibliographical note
Publisher Copyright:© 2018, Institute of Chemistry, Slovak Academy of Sciences.
Keywords
- 6-hydroxyaurones
- Aminomethylation
- Mannich base
- Prostate cancer
ASJC Scopus subject areas
- General Chemistry
- Biochemistry
- General Chemical Engineering
- Industrial and Manufacturing Engineering
- Materials Chemistry