Citation: Zhang Ying, Lü Mengjiao, Zhang Yaling, Chen Li, Wang Wei, Li Baolin. Synthesis and Antitumor Activity of Heterozygous Isatin-Quinazoline Compounds[J]. Chinese Journal of Organic Chemistry, ;2017, 37(7): 1787-1793. doi: 10.6023/cjoc201701037 shu

Synthesis and Antitumor Activity of Heterozygous Isatin-Quinazoline Compounds

Key Laboratory of Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, School of Chemistry & Chemical Engineering, Shaanxi Normal University, Xi'an 710062

Corresponding author: Wang Wei, wwlzz@snnu.edu.cn Li Baolin, baolinli@snnu.edu.cn
Received Date: 18 January 2017
Revised Date: 20 February 2017
Available Online: 8 July 2017
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21272144)National Natural Science Foundation of China 21272144

Figures(3)

Nine new heterozygous isatin-quinazoline compounds were synthesized from cheap and easily available ortho nitrobenzaldehyde as the starting material. The chemical structures of the synthesized compounds were characterized by NMR, IR and HRMS. The structure of (E)-3-(((E)-(5-(4-((3-ethynylphenyl)amino)quinazolin-6-yl)furan-2-yl)methylene)hydrazono)-indolin-2-one (4a) was further determined by crystallization and X-ray diffraction, and the data revealed that its cis-trans isomerism was (E, E). The antitumor activity of these new compounds was evaluated in vitro by methyl thiazolyl tetrazolium (MTT) assay in human colorectal carcinoma cells SW480, human non-small cell lung cancer cells A549 and NCI^- H1975, and human epidermoid squamous carcinoma cells A431. The preliminary data demonstrated that most of the synthetic compounds had moderate to potent inhibitory activity against these four tumor cell lines. In particular, compound 4a had highly potent inhibitory activity on proliferation of four cell lines, and the activity was more potent than positive lapatinib.
- isatin,
- quinazoline,
- synthesis,
- antitumor activity
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