Synthesis and Pharmacological Properties of 5-Alkyl Substituted Nicotine Analogs

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...

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Bibliographic Details
Published in:Chinese journal of chemistry 2012-12, Vol.30 (12), p.2813-2818
Main Authors: Wang, Jing, Li, Xi, Yuan, Qianjia, Ren, Jiangmeng, Huang, Jin, Zeng, Bubing
Format: Article
Language:English
Subjects:
asymmetric synthesis
biological activities
nicotine analog
Vilsmeier reaction
叠氮化物
合成
尼古丁
烷基取代
生物活性
类似物
药理特性
高烯丙基醇
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Summary: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 ICs0 values against RD and SY-SY5Y.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.201200952