Synthesis and cytotoxic evaluation of hybrids of indolin-2-one and quinazoline-4(3H)-one linked via carbon-carbon double bond

doi:10.5246/jcps.2014.11.097

Journal of Chinese Pharmaceutical Sciences ›› 2014, Vol. 23 ›› Issue (11): 765-771.DOI: 10.5246/jcps.2014.11.097

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Synthesis and cytotoxic evaluation of hybrids of indolin-2-one and quinazoline-4(3H)-one linked via carbon-carbon double bond

Boying Shi^1,3, Jingjing Zhang¹, Shengli Cao^1*, Man Gao¹, Panpan Ding¹, Zhongfeng Li¹, Ji Liao², Xingzhi Xu^2*

1. Department of Chemistry, Capital Normal University, Beijing 100048, China
2. Beijing Key Laboratory of DNA Damage Response; College of Life Science, Capital Normal University, Beijing 100048, China
3. Patent Examination Cooperation Center of the Patent Office, SIPO, Beijing 100081, China

Received:2014-06-10 Revised:2014-07-26 Online:2014-11-24 Published:2014-08-01
Contact: Tel.: 86-10-68902974, 86-10-68902240
Supported by:
National Natural Science Foundation of China (Grant No. 20972099, 31130017), Beijing Municipal Commission of Education (Grant No. KZ201210028035), Scientific Research Base Development Program of the Beijing Municipal Commission of Education, and the 973 Project (Grant No. 2013CB911000).

Abstract

Abstract:

A novel series of compounds combining indolin-2-one and quinazolin-4(3H)-one moietyvia a carbon-carbon double bond were synthesized by aldol-condensation of 2-methylquinazolin-4(3H)-one-6-carbaldehyde with various indolin-2-ones. The synthesized compounds were evaluated for their cytotoxic activity against five human cancer cell lines, namely, A549, MCF-7, HeLa, HT-29 and HCT-116. We found that compound 5e with two bromine atoms at the 5- and 7-positions of the indolin-2-one ring was most potent, which inhibited proliferation of five cancer cell lines in the range of32.0%–62.3% at a concentration of 50 µM. Our results further indicate that the connection of 5,7-dibromoindolin-2-one and 2-methylquinazolin-4(3H)-one moiety witha carbon-carbon double bondis essential for compound 5e to exert cytotoxicity.

Key words: Indolin-2-one, Quinazolin-4(3H)-one, Cytotoxic activity

CLC Number:

R916.4

Supporting:

Boying Shi, Jingjing Zhang, Shengli Cao, Man Gao, Panpan Ding, Zhongfeng Li, Ji Liao, Xingzhi Xu. Synthesis and cytotoxic evaluation of hybrids of indolin-2-one and quinazoline-4(3H)-one linked via carbon-carbon double bond[J]. Journal of Chinese Pharmaceutical Sciences, 2014, 23(11): 765-771.

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Synthesis and cytotoxic evaluation of hybrids of indolin-2-one and quinazoline-4(3H)-one linked via carbon-carbon double bond

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