Design, synthesis and anti-tumor activity of N-Phenyl-2-(4-phenyl)-cyclo-propane-1-carboxylic acid-1-amide

CHEN Huan; GENG Dong-ping; LI Ke

doi:10.3969/j.issn.1006-0111.2012.06.007

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Objective To design, synthesize and study the anti-tumor activity in vitro of N-Phenyl-2-(4-phenyl)-cyclopropane-1-carboxylic acid-1-amide compounds. Methods The target compounds were obtained through knoevenagel condensation, cyclization, hydrolysis and amidation reaction, microwave reaction equipment contributed to improve efficiency. Structure of the target compounds were determined by ¹H NMR and LC-MS. Results Design, synthesis of 20 novel cyclopropyl-amide compounds and anti-tumor assay showed all of the target compounds had significant anticancer activity in vitro. Compound 5b had the best activity in A549 cell with IC₅₀ 6.8 μM. Conclusion 4-trifluoromethyl substituted phenyl compounds had better anticancer activity than 4-chlorine substituted phenyl compounds.Electron-withdrawing group made more contributed than electron-donating group for anticancer activity in vitro.

Design, synthesis and anti-tumor activity of N-Phenyl-2-(4-phenyl)-cyclo-propane-1-carboxylic acid-1-amide

Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2012-04-16

Rev Recd Date: 2012-06-08

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Abstract: Objective To design, synthesize and study the anti-tumor activity in vitro of N-Phenyl-2-(4-phenyl)-cyclopropane-1-carboxylic acid-1-amide compounds. Methods The target compounds were obtained through knoevenagel condensation, cyclization, hydrolysis and amidation reaction, microwave reaction equipment contributed to improve efficiency. Structure of the target compounds were determined by ¹H NMR and LC-MS. Results Design, synthesis of 20 novel cyclopropyl-amide compounds and anti-tumor assay showed all of the target compounds had significant anticancer activity in vitro. Compound 5b had the best activity in A549 cell with IC₅₀ 6.8 μM. Conclusion 4-trifluoromethyl substituted phenyl compounds had better anticancer activity than 4-chlorine substituted phenyl compounds.Electron-withdrawing group made more contributed than electron-donating group for anticancer activity in vitro.

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Design, synthesis and anti-tumor activity of N-Phenyl-2-(4-phenyl)-cyclo-propane-1-carboxylic acid-1-amide

doi: 10.3969/j.issn.1006-0111.2012.06.007

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通讯作者: 陈斌, [email protected]

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