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Systematic Synthetic Stuchies on Bioactive Alkaloids and Their Biokeical Activiiies

生物活性生物碱及其生物活性的系统合成研究

基本信息

批准号：
18580104
负责人：
MAKABE Hidefumi
金额：
$ 2.17万
依托单位：
Shinshu University
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
2006
资助国家：
日本
起止时间：
2006 至 2007
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-18580104/
关键词：
organic chemistry synthetic chemistry biological activity

项目摘要

A number of alkaloids have been burl abundantly in nature and marry of than show interesting pharmalogical adivitites. Due to the amount of elk: slide is limited from the native, it is very important to prepare these compounds in order to study their binlogical properties. The aim of this study is to construct these compounds systenatically and solve the mechanism of action.1. Synthetic studies on spectamine ARecentlty spectiamine A was isolated by Ramo and m-workers at Shinshu Univemity icon African legume, (Is s i a apectahilis and identified as °Obenzoyl derivative of (+)-iso6-cassine. The key reaction of the synthesis of spectamine A is Pd-catayzed stereceelective cyclization to afford 2,6-traos-piperidine ring. When Pd.^2(dba)^3 was used as a catalyst and Cbm was used as a protecting group, the ratio of trail/cis was 79/21. The total synthesis of spectamine A is currently under way.2. Synthess of pyranicynTotal synthesis of pyranicin was achieved using C12Pd(CH3CN)2-catalyzed diastereoselective cyclization of the allyfic ester as the key step. The inhibitory activity of this compound for mitochiondrial NADH-uhiquioone oxidoreductase (complex I) was slightly poorer than that of ordinary mono-THF acetogenins such as cis-solamin. In the course of this study synthesis and determination of the absolute configuration of tookinelin was aka achieved.

许多生物碱在自然界中含量丰富，并表现出有趣的药理学活性。由于麋鹿：幻灯片的数量有限，因此制备这些化合物以研究其双逻辑特性非常重要。本研究的目的是系统构建这些化合物并解析其作用机制。 1．观胺 A 的合成研究最近，观胺 A 是由 Ramo 和 m-workers 在信州大学图标非洲豆科植物（Is s i a apectahilis）中分离出来的，并被鉴定为 (+)-iso6-cassine 的°O苯甲酰衍生物。合成观胺 A 的关键反应是 Pd 催化的立体选择性环化，以提供 2,6-反式哌啶环。当Pd.^2(dba)^3用作催化剂并且Cbm用作保护基时，trail/cis的比率为79/21。目前Specamine A的全合成正在进行中。 2．吡喃霉素的合成利用C12Pd(CH3CN)2催化实现了吡喃霉素的全合成烯丙酯的非对映选择性环化是关键步骤。该化合物对线粒体 NADH-uhiquioone 氧化还原酶（复合物 I）的抑制活性比普通单 THF 乙酰苷如顺式索拉明的抑制活性稍差。在本研究过程中，实现了takeinelin绝对构型的合成和测定。