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Citation: CAO Sheng-Li, FENG Yu-Ping, ZHANG Mei, JIANG Yu-Yang, YU Xiao-Qing, MO Zhuo-Hua. Synthesis and Evaluation of 4(3H)-Quinazolinone Derivatives Bearing Aromatic Amine Side Chains as Antitumor Agents[J]. Chinese Journal of Applied Chemistry, ;2007, 24(2): 162-167. shu

Synthesis and Evaluation of 4(3H)-Quinazolinone Derivatives Bearing Aromatic Amine Side Chains as Antitumor Agents

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a Department of Chemistry, Capital Normal University, Beijing 100037;
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b The Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Ministry of Education;Department of Chemistry, Tsinghua University, Beijing;
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c The Key Laboratory of Chemical Biology, Guangdong Province;Graduate School at Shenzhen, Tsinghua University, Shenzhen

Corresponding author: CAO Sheng-Li,
Received Date: 16 March 2006
Available Online: 26 July 2006
Fund Project: 北京市自然科学基金(7042006) (7042006)北京市优秀人才培养专项经费(20041D0501601)资助项目 (20041D0501601)

Based on the structural feature of nonclassical antifolates,a series of 4(3H)-quinazolinone deriva-tives bearing aromatic amine side chains have been designed by incorporating trimethoxyphenyl,an antitumor pharmacophore,with 4(3H)-quinazolinone.N-alkylation of 3,4,5-trimethoxyphenylamine with appropriate a-mount of alkyl halides afforded 4 kinds of N-substituted 3,4,5-trimethoxyphenylamines in 30.3%~60.6% yields.The target compounds 8a~8m were obtained through the reactions of 6-bromo-2-methyl-4(3H)-quin-azolinone with 3,4,5-trimethoxyphenylamine,N-substituted 3,4,5-trimethoxyphenylamines or other aryl-amines at room temperature in 30.8%~71.9% yields,and their structures were confirmed by means of ESI-MS,¹H NMR,elemental analysis or HRMS.The in vitro cytotoxicities against A-549(human non-small cell lung cancer),HCT-8(human colon cancer) and Bel-7402(human liver cancer) cell lines of the synthesized compounds 8a~8m were tested with colorimetric MTT assay,and the results indicated that the percent growth inhibition against A-549,HCT-8 and Bel-7402 cell lines at 5×10^-6g/mL concentration of the compounds 8a~8m were all lower than 25%.
- 4(3H)-quinazolinone derivative,
- synthesis,
- antitumor activity,
- MTT assay
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