Synthesis and Antitumor Activities of 3-[(4'-Morpholine)-carbonyl or ethoxycarbonyl]-4-anilinoqunolines

doi:10.7503/cjcu20111217

Chem. J. Chinese Universities ›› 2012, Vol. 33 ›› Issue (10): 2249.doi: 10.7503/cjcu20111217

• Organic Chemistry • Previous Articles Next Articles

Synthesis and Antitumor Activities of 3-[(4'-Morpholine)-carbonyl or ethoxycarbonyl]-4-anilinoqunolines

LIU Dan¹, ZHU Xiu-Jie¹, JIANG Meng¹, CHEN Hong², LAN Shuai-Peng¹

1. Department of Pharmaceutical Engineering, Shenyang University of Chemical Technology, Shenyang 110142, China;
2. Department of Pharmacognosy, Medical College of Chinese People's Armed Police Forces, Tianjin 300162, China

Received:2011-12-26 Online:2012-10-10 Published:2012-09-12

Abstract

Abstract:

Sixteen new 4-anilinoqunolines with 4'-morpholine-carbonyl group or ethoxycarbonyl group at C3 position(Ⅰ₁-Ⅰ₁₀, Ⅱ₁-Ⅱ₆) were designed and synthesized from 3-chlorobenzenamine and ethoxymethylene malonic diethyl ester(EMME) by the condensation, high-temperature cyclization, hydrolysis and nucleophilic substitution reaction. Their structures were confirmed by MS and ¹H NMR analysis. The antitumor activities of these compounds were evaluated by MTT assay in HeLa, HepG2 and BGC-823 cells expressing high levels of epidermal growth factor receptor(EGFR). These compounds exhibited somewhat inhibitory activities against the three cancer cells. Among them, compounds Ⅱ₄-Ⅱ₆ had stronger inhibition on HepG2 cell and Ⅱ₁, Ⅱ₅ had stronger activity on BGC-823 cell. Preliminary structure-activity relationship was also discussed.

Key words: 4-Anilinoquinoline, Tumor, Epidermal growth factor receptor(EGFR), Tyrosine kinase, Inhibitor

CLC Number:

O626.3

TrendMD:

LIU Dan, ZHU Xiu-Jie, JIANG Meng, CHEN Hong, LAN Shuai-Peng. Synthesis and Antitumor Activities of 3-[(4'-Morpholine)-carbonyl or ethoxycarbonyl]-4-anilinoqunolines[J]. Chem. J. Chinese Universities, 2012, 33(10): 2249.

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Synthesis and Antitumor Activities of 3-[(4'-Morpholine)-carbonyl or ethoxycarbonyl]-4-anilinoqunolines

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