Design, Synthesis and Activity Evaluation of N-Substituted Phthalimide Derivatives

doi:10.7503/cjcu20130298

Abstract

Abstract:

One novel compound 3,5-dimethoxy phthalimide had been isolated from Lasiosphaera fenzlii Reich. The compound exhibited definite antioxidant activity. Meanwhile it was reported that many compounds with the skeleton of phthalimide displayed many bioactivities such as anti-angiogenesis, anti-inflammatory, immune regulation and anti-tumor and so on. On the comprehensive review of above evidences, a series of N-substituted-3,5-dimethoxy phthalimide derivatives and N-substituted-3,5-dihydroxy phthalimide derivatives were designed and synthesized. Those compounds were synthesized by the multi-step reaction, 3,5-dimethoxybenzoic acid was used as a starting material, and sequentially generates the phthalic anhydride and phthalimide, then reacted with a series of halogenated hydrocarbons, and stripped of methyl to obtain the target compounds. Thirty-one new compounds were synthesized, and the structures were characterized by ¹H NMR, ¹³C NMR and MS techniques. Their anti-tumor and anti-angiogenesis activities against A549 and HUVEC cell line in vitro were tested. Some compounds showed a certain activity.

Key words: Lasiosphaera fenzlii Reich., Phthalimide, N-Substituted, Thalidomide, Anti-tumor

CLC Number:

O621

TrendMD:

QIN Si-Ning, LÜ Wen-Wen, WANG Quan, ZHAO Qing-Chun, XU Yong-Nan. Design, Synthesis and Activity Evaluation of N-Substituted Phthalimide Derivatives[J]. Chem. J. Chinese Universities, 2013, 34(12): 2745.

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