Efficient synthesis of aurone Mannich bases and evaluation of their antineoplastic activity in PC-3 prostate cancer cells

Antonina V. Popova, Mykhaylo S. Frasinyuk, Svitlana P. Bondarenko, Wen Zhang, Yanqi Xie, Zachary M. Martin, Xianfeng Cai, Michael V. Fiandalo, James L. Mohler, Chunming Liu, David S. Watt, Vitaliy M. Sviripa

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

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 languageEnglish
Pages (from-to)2443-2456
Number of pages14
JournalChemical Papers
Volume72
Issue number10
DOIs
StatePublished - 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

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