文献类型：期刊文献

英文题名：Synthesis and Pharmacological Properties of 5-Alkyl Substituted Nicotine Analogs

作者：Wang Jing[1];Li Xi[1];Yuan Qianjia[1];Ren Jiangmeng[1];Huang Jin[1];Zeng Bubing[1]

机构：[1]E China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China

年份：2012

卷号：30

期号：12

起止页码：2813

外文期刊名：CHINESE JOURNAL OF CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000312942500015)】；

基金：Financial support of this work from Shanghai Foundation of Science and Technology (No. 09JC1404200), the National "863" Project of China (No. 2007AA02Z301), "111" Project and the Fundamental Research Funds for the Central University (No. WY1113007) are gratefully acknowledged.

语种：英文

外文关键词：nicotine analog; asymmetric synthesis; Vilsmeier reaction; biological activities

摘要：This paper describes a concise and practical route to enantiomerically enriched 5-alkyl substituted nicotine analogs. The Vilsmeier reaction was used to construct the nicotinaldehydes ring followed by the introduction of the chiral homoallylic alcohol by organic boron reagent and the cyclization of the pyrrolidine ring through the reduction of a chiral azide. 17 analogs have been synthesized and their corresponding biological activities were tested, in which compounds 10d and 10g exhibit excellent IC50 values against RD and SY-SY5Y.