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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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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cited_by cdi_FETCH-LOGICAL-c3812-e7256a0c4d3a7ddc8079f76e20295b60f25623f068fcb28465a0304b9e6cb6bd3
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container_end_page 2818
container_issue 12
container_start_page 2813
container_title Chinese journal of chemistry
container_volume 30
creator Wang, Jing
Li, Xi
Yuan, Qianjia
Ren, Jiangmeng
Huang, Jin
Zeng, Bubing
description 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.
doi_str_mv 10.1002/cjoc.201200952
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source Wiley-Blackwell Read & Publish Collection
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
title Synthesis and Pharmacological Properties of 5-Alkyl Substituted Nicotine Analogs
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