Synthesis and in vitro cytotoxic evaluation of novel N-(3,4,5- trimethoxyphenyl)pyridin-2(1H)-one derivatives

Taijie Chen; Yu Luo; Li Sheng; Jia Li; Youhong Hu; Wei Lu

doi:10.1007/s11030-013-9442-1

Synthesis and in vitro cytotoxic evaluation of novel N-(3,4,5- trimethoxyphenyl)pyridin-2(1H)-one derivatives

Taijie Chen, Yu Luo^*, Li Sheng, Jia Li, Youhong Hu, Wei Lu

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

4 Scopus citations

Abstract

A series of novel N-(3,4,5-trimethoxyphenyl)pyridin-2(1H)-one derivatives were designed, synthesized, and evaluated for their in vitro cytotoxicity against human colon cancer cells HCT-116. The key steps involved consecutive Chan-Lam- and Buchwald-Hartwig couplings. Most of these C-6 substituted pyridone derivatives showed moderate antiproliferative activity. The preliminary SAR indicated that the conformationally restricted pyridones exhibited more potent cytotoxicity than the flexible counterparts. In addition, cell cycle analysis of the selected compounds 4b and e showed a G2/M arrest, suggesting a possible antitubulin mechanism for these novel pyridone derivatives.

Original language	English
Pages (from-to)	435-444
Number of pages	10
Journal	Molecular Diversity
Volume	17
Issue number	3
DOIs	https://doi.org/10.1007/s11030-013-9442-1
State	Published - Aug 2013

Keywords

Buchwald-Hartwig coupling reaction
Cell cycle
Chan-Lam coupling reaction
Combretastatin A-4
Cytotoxicity
HCT-116
Pyridin-2(1H)-one

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title = "Synthesis and in vitro cytotoxic evaluation of novel N-(3,4,5- trimethoxyphenyl)pyridin-2(1H)-one derivatives",

abstract = "A series of novel N-(3,4,5-trimethoxyphenyl)pyridin-2(1H)-one derivatives were designed, synthesized, and evaluated for their in vitro cytotoxicity against human colon cancer cells HCT-116. The key steps involved consecutive Chan-Lam- and Buchwald-Hartwig couplings. Most of these C-6 substituted pyridone derivatives showed moderate antiproliferative activity. The preliminary SAR indicated that the conformationally restricted pyridones exhibited more potent cytotoxicity than the flexible counterparts. In addition, cell cycle analysis of the selected compounds 4b and e showed a G2/M arrest, suggesting a possible antitubulin mechanism for these novel pyridone derivatives.",

keywords = "Buchwald-Hartwig coupling reaction, Cell cycle, Chan-Lam coupling reaction, Combretastatin A-4, Cytotoxicity, HCT-116, Pyridin-2(1H)-one",

author = "Taijie Chen and Yu Luo and Li Sheng and Jia Li and Youhong Hu and Wei Lu",

year = "2013",

month = aug,

doi = "10.1007/s11030-013-9442-1",

language = "英语",

volume = "17",

pages = "435--444",

journal = "Molecular Diversity",

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T1 - Synthesis and in vitro cytotoxic evaluation of novel N-(3,4,5- trimethoxyphenyl)pyridin-2(1H)-one derivatives

AU - Chen, Taijie

AU - Luo, Yu

AU - Sheng, Li

AU - Li, Jia

AU - Hu, Youhong

AU - Lu, Wei

PY - 2013/8

Y1 - 2013/8

N2 - A series of novel N-(3,4,5-trimethoxyphenyl)pyridin-2(1H)-one derivatives were designed, synthesized, and evaluated for their in vitro cytotoxicity against human colon cancer cells HCT-116. The key steps involved consecutive Chan-Lam- and Buchwald-Hartwig couplings. Most of these C-6 substituted pyridone derivatives showed moderate antiproliferative activity. The preliminary SAR indicated that the conformationally restricted pyridones exhibited more potent cytotoxicity than the flexible counterparts. In addition, cell cycle analysis of the selected compounds 4b and e showed a G2/M arrest, suggesting a possible antitubulin mechanism for these novel pyridone derivatives.

AB - A series of novel N-(3,4,5-trimethoxyphenyl)pyridin-2(1H)-one derivatives were designed, synthesized, and evaluated for their in vitro cytotoxicity against human colon cancer cells HCT-116. The key steps involved consecutive Chan-Lam- and Buchwald-Hartwig couplings. Most of these C-6 substituted pyridone derivatives showed moderate antiproliferative activity. The preliminary SAR indicated that the conformationally restricted pyridones exhibited more potent cytotoxicity than the flexible counterparts. In addition, cell cycle analysis of the selected compounds 4b and e showed a G2/M arrest, suggesting a possible antitubulin mechanism for these novel pyridone derivatives.

KW - Buchwald-Hartwig coupling reaction

KW - Cell cycle

KW - Chan-Lam coupling reaction

KW - Combretastatin A-4

KW - Cytotoxicity

KW - HCT-116

KW - Pyridin-2(1H)-one

UR - https://www.scopus.com/pages/publications/84880834169

U2 - 10.1007/s11030-013-9442-1

DO - 10.1007/s11030-013-9442-1

M3 - 文章

C2 - 23612851

AN - SCOPUS:84880834169

SN - 1381-1991

VL - 17

SP - 435

EP - 444

JO - Molecular Diversity

JF - Molecular Diversity

IS - 3

ER -

Synthesis and in vitro cytotoxic evaluation of novel N-(3,4,5- trimethoxyphenyl)pyridin-2(1H)-one derivatives

Abstract

Keywords

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