Studies on analogues of huperzine A for treatment of senile dementia VI. Asymmetric total synthesis of 14-nor-huperzine A and its inhibitory activity of acetylcholinesterase
文献类型：期刊论文
| 作者 | He Xuchang; Yu Gengli; Bai Donglu
|
| 刊名 | Acta Pharmaceutica Sinica
 |
| 出版日期 | 2003 |
| 卷号 | 38期号:5页码:346-349 |
| 关键词 | huperzine A asymmetric synthesis acetylcholinesterase inhibitor chiral ferrocenylphosphine ligands |
| ISSN号 | 0513-4870 |
| 其他题名 | 老年痴呆症药物石杉碱甲类似物研究VI(-)-14-去甲基石杉碱甲的不对称全合成及其乙酰胆碱酯酶抑制活性 |
| 文献子类 | Article |
| 英文摘要 | Aim To study asymmetric total synthesis of 14-nor-huperzine A 2 and its inhibitory activity on acetylcholinesterase. Methods Highly enantioselective synthesis of compound 5 from beta-keto-ester 3 and 2-methylene-1, 3-propanediol diacetate 4 by palladium-catalyzed bicycloannulation was carried out using new chiral ferrocenylphosphine ligands, such as 10, 11, followed by regioselective double-bond migration to produce compound 6. Optically pure 6 was obtained after enantio-enrichment recrystallization. Then, according to similar procedures of huperzine A synthesis, the target compound 14-nor-huperzine A 2 was prepared. The inhibitory activity was tested with rat erythrocyte membrame acetylcholinesterase. Results The inhibitory activity of synthetic ( - )-14-nor-huperzine A was 8 fold less potent than that of ( - )-huperzine A. Conclusion A hydrogen-bond between 14-methyl group of ( - ) huperzine A and the main-chain oxygen of His 440 is necessary for the highly acetylcholinesterase inhibitory activity of huperzine A. |
| 资助项目 | 国家自然科学基金资助项目(30070865)[00000000] |
| WOS研究方向 | Pharmacology & Pharmacy (provided by Clarivate Analytics) |
| 语种 | 中文 |
| CSCD记录号 | CSCD:1344081 |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/268469]  |
| 专题 | 院士及顾问专家 |
| 作者单位 | Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 200031, China. |
| 推荐引用方式 GB/T 7714 | He Xuchang,Yu Gengli,Bai Donglu. Studies on analogues of huperzine A for treatment of senile dementia VI. Asymmetric total synthesis of 14-nor-huperzine A and its inhibitory activity of acetylcholinesterase[J]. Acta Pharmaceutica Sinica,2003,38(5):346-349. |
| APA | He Xuchang,Yu Gengli,&Bai Donglu.(2003).Studies on analogues of huperzine A for treatment of senile dementia VI. Asymmetric total synthesis of 14-nor-huperzine A and its inhibitory activity of acetylcholinesterase.Acta Pharmaceutica Sinica,38(5),346-349. |
| MLA | He Xuchang,et al."Studies on analogues of huperzine A for treatment of senile dementia VI. Asymmetric total synthesis of 14-nor-huperzine A and its inhibitory activity of acetylcholinesterase".Acta Pharmaceutica Sinica 38.5(2003):346-349. |
入库方式： OAI收割
来源：上海药物研究所
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