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

doi:10.1007/s11696-018-0485-8

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

Molecular and Cellular Biochemistry

Research output: Contribution to journal › Article › peer-review

14 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 language	English
Pages (from-to)	2443-2456
Number of pages	14
Journal	Chemical Papers
Volume	72
Issue number	10
DOIs	https://doi.org/10.1007/s11696-018-0485-8
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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1007/s11696-018-0485-8

Cite this

Popova, A. V., Frasinyuk, M. S., Bondarenko, S. P., Zhang, W., Xie, Y., Martin, Z. M., Cai, X., Fiandalo, M. V., Mohler, J. L., Liu, C., Watt, D. S., & Sviripa, V. M. (2018). Efficient synthesis of aurone Mannich bases and evaluation of their antineoplastic activity in PC-3 prostate cancer cells. Chemical Papers, 72(10), 2443-2456. https://doi.org/10.1007/s11696-018-0485-8

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

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.]",

keywords = "6-hydroxyaurones, Aminomethylation, Mannich base, Prostate cancer",

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

note = "Publisher Copyright: {\textcopyright} 2018, Institute of Chemistry, Slovak Academy of Sciences.",

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doi = "10.1007/s11696-018-0485-8",

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T1 - Efficient synthesis of aurone Mannich bases and evaluation of their antineoplastic activity in PC-3 prostate cancer cells

AU - Popova, Antonina V.

AU - Frasinyuk, Mykhaylo S.

AU - Bondarenko, Svitlana P.

AU - Zhang, Wen

AU - Xie, Yanqi

AU - Martin, Zachary M.

AU - Cai, Xianfeng

AU - Fiandalo, Michael V.

AU - Mohler, James L.

AU - Liu, Chunming

AU - Watt, David S.

AU - Sviripa, Vitaliy M.

PY - 2018/10/1

Y1 - 2018/10/1

N2 - 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.]

AB - 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.]

KW - 6-hydroxyaurones

KW - Aminomethylation

KW - Mannich base

KW - Prostate cancer

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

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