• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

含1,4-苯并二氧六环部分的 -二氢水仙环素衍生物的立体选择性合成。

Stereoselective synthesis of -dihydronarciclasine derivatives containing a 1,4-benzodioxane moiety.

作者信息

Varró Gábor, Pogrányi Balázs, Grün Alajos, Simon András, Hegedűs László, Kádas István

机构信息

1Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budafoki út 8, Budapest, 1111 Hungary.

2Gedeon Richter Plc., Gyömrői út 19-21, Budapest, 1103 Hungary.

出版信息

Monatsh Chem. 2018;149(12):2265-2285. doi: 10.1007/s00706-018-2287-7. Epub 2018 Oct 26.

DOI:10.1007/s00706-018-2287-7
PMID:32214482
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7087796/
Abstract

ABSTRACT

Some new -dihydronarciclasine derivatives containing a 1,4-benzodioxane moiety were stereoselectively synthesised using our feasible and efficient method developed recently. These new phenanthridone alkaloid analogues were obtained in both racemic and optically active forms. High enantioselectivities (up to 99% ) were achieved by applying (8,9)-9-amino(9-deoxy)epiquinine as an organocatalyst. Due to a side reaction, various methoxyphenanthridine regioisomers were also prepared which afforded further synthetic -dihydronarciclasine analogues modified in the ring A of the phenanthridone scaffold.

摘要

摘要

采用我们最近开发的可行且高效的方法，立体选择性地合成了一些含有1,4 -苯并二氧六环部分的新型二氢水仙环素衍生物。这些新的菲啶酮生物碱类似物以消旋体和旋光活性形式获得。通过使用(8,9)-9 -氨基(9 -脱氧)表奎宁作为有机催化剂，实现了高对映选择性(高达99%)。由于副反应，还制备了各种甲氧基菲啶区域异构体，这些异构体为菲啶酮骨架A环修饰的二氢水仙环素类似物的进一步合成提供了原料。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/7c18782dfb31/706_2018_2287_Sch6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/6222691419d3/706_2018_2287_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/0f0edf242b58/706_2018_2287_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/2cdcf5ee5834/706_2018_2287_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/e5762838751f/706_2018_2287_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/5571fd97c388/706_2018_2287_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/8e74b9db8edd/706_2018_2287_Sch3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/9a2f1392fa6f/706_2018_2287_Sch4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/3941afc69aac/706_2018_2287_Sch5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/72a7e3ea78a8/706_2018_2287_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/7c18782dfb31/706_2018_2287_Sch6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/6222691419d3/706_2018_2287_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/0f0edf242b58/706_2018_2287_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/2cdcf5ee5834/706_2018_2287_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/e5762838751f/706_2018_2287_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/5571fd97c388/706_2018_2287_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/8e74b9db8edd/706_2018_2287_Sch3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/9a2f1392fa6f/706_2018_2287_Sch4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/3941afc69aac/706_2018_2287_Sch5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/72a7e3ea78a8/706_2018_2287_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ca3b/7087796/7c18782dfb31/706_2018_2287_Sch6_HTML.jpg

相似文献

1
Stereoselective synthesis of -dihydronarciclasine derivatives containing a 1,4-benzodioxane moiety.含1,4-苯并二氧六环部分的 -二氢水仙环素衍生物的立体选择性合成。
Monatsh Chem. 2018;149(12):2265-2285. doi: 10.1007/s00706-018-2287-7. Epub 2018 Oct 26.
2
The First Enantioselective Total Synthesis of (-)-trans-Dihydronarciclasine.(-)-反式-二氢纳曲酮的首次对映选择性全合成。
J Nat Prod. 2017 Jun 23;80(6):1909-1917. doi: 10.1021/acs.jnatprod.7b00208. Epub 2017 Jun 5.
3
(±)-trans-Dihydronarciclasine and (±)-trans-dihydrolycoricidine analogues modified in their ring A: Evaluation of their anticancer activity and a SAR study.（±）-反式二氢那可丁和（±）-反式二氢石蒜碱类似物在其 A 环上的修饰：抗癌活性评价及构效关系研究。
Eur J Med Chem. 2019 Jul 1;173:76-89. doi: 10.1016/j.ejmech.2019.04.010. Epub 2019 Apr 8.
4
Stereocontrolled total synthesis of (+)-trans-dihydronarciclasine.（+）-反式-二氢纳曲酮的立体控制全合成。
Chemistry. 2012 Aug 6;18(32):9977-82. doi: 10.1002/chem.201201649. Epub 2012 Jul 10.
5
Isolation and structural modification of 7-deoxynarciclasine and 7-deoxy-trans-dihydronarciclasine.7-脱氧水仙环素和7-脱氧反式二氢水仙环素的分离与结构修饰
J Nat Prod. 2006 Jan;69(1):7-13. doi: 10.1021/np058068l.
6
Stereoselective synthesis of functionalised carbocyclic amides: construction of the syn-(4aS,10bS)-phenanthridone skeleton.手性合成功能化碳环酰胺：顺式-(4aS,10bS)-菲啶酮骨架的构建。
Org Biomol Chem. 2012 May 21;10(19):3937-45. doi: 10.1039/c2ob25334h. Epub 2012 Apr 4.
7
Lipase-catalyzed kinetic resolution of cyclic trans-1,2-diols bearing a diester moiety: synthetic application to chiral seven-membered-ring alpha,alpha-disubstituted alpha-amino acid.脂肪酶催化的带有二酯部分的环状反式-1,2-二醇的动力学拆分：在手性七元环α,α-二取代α-氨基酸合成中的应用
J Org Chem. 2007 Sep 28;72(20):7750-6. doi: 10.1021/jo701317d. Epub 2007 Aug 22.
8
Antiviral alkaloid principles of the plant family Amaryllidaceae.石蒜科植物的抗病毒生物碱成分。
Phytomedicine. 2023 Jan;108:154480. doi: 10.1016/j.phymed.2022.154480. Epub 2022 Oct 11.
9
Total synthesis of zoanthamine alkaloids.獐牙菜苦苷类生物碱的全合成。
Acc Chem Res. 2012 May 15;45(5):746-55. doi: 10.1021/ar200267a. Epub 2012 Feb 16.
10
Synthesis and evaluation of C-ring aromatized analogues of phenanthridone alkaloids.合成及评价菲啶酮类生物碱 C 环芳构化类似物。
Arch Pharm Res. 2011 Jul;34(7):1065-70. doi: 10.1007/s12272-011-0703-1. Epub 2011 Aug 3.

本文引用的文献

1
The First Enantioselective Total Synthesis of (-)-trans-Dihydronarciclasine.(-)-反式-二氢纳曲酮的首次对映选择性全合成。
J Nat Prod. 2017 Jun 23;80(6):1909-1917. doi: 10.1021/acs.jnatprod.7b00208. Epub 2017 Jun 5.
2
Unnatural C-1 homologues of pancratistatin - Synthesis and promising biological activities.棒曲霉素的非天然C-1同系物——合成及有前景的生物活性。
Can J Chem. 2012;90(11):932-943. doi: 10.1139/v2012-073. Epub 2012 Sep 19.
3
iPSC Neuronal Assay Identifies Amaryllidaceae Pharmacophore with Multiple Effects against Herpesvirus Infections.
诱导多能干细胞神经元检测鉴定出对疱疹病毒感染具有多种作用的石蒜科药效基团。
ACS Med Chem Lett. 2015 Nov 19;7(1):46-50. doi: 10.1021/acsmedchemlett.5b00318. eCollection 2016 Jan 14.
4
Synthesis and biological evaluation of unnatural derivatives of narciclasine: 7-aza-nornarciclasine and its N-oxide.水仙环素非天然衍生物的合成与生物学评价：7-氮杂去甲水仙环素及其N-氧化物
Bioorg Med Chem Lett. 2014 Sep 1;24(17):4236-8. doi: 10.1016/j.bmcl.2014.07.034. Epub 2014 Jul 19.
5
Synthesis and cytotoxicity of (+/-)-7,9-dideoxy-pancratistatin analogues.（+/-）-7,9-去氧巴卡丁类似物的合成及细胞毒性。
Org Biomol Chem. 2013 Jan 21;11(3):515-22. doi: 10.1039/c2ob27127c. Epub 2012 Dec 3.
6
Amaryllidaceae alkaloids inhibit nuclear-to-cytoplasmic export of ribonucleoprotein (RNP) complex of highly pathogenic avian influenza virus H5N1.石蒜科生物碱抑制高致病性禽流感病毒 H5N1 的核质输出核糖核蛋白（RNP）复合物。
Influenza Other Respir Viruses. 2013 Nov;7(6):922-31. doi: 10.1111/irv.12035. Epub 2012 Nov 8.
7
Synthesis of C-1 homologues of pancratistatin and their preliminary biological evaluation.C-1 同系物的合成及其初步的生物评估。
Bioorg Med Chem Lett. 2011 Aug 15;21(16):4750-2. doi: 10.1016/j.bmcl.2011.06.068. Epub 2011 Jun 22.
8
Synthesis and glycogen phosphorylase inhibitor activity of functionalized 1,4-benzodioxanes.功能化1,4-苯并二氧六环的合成及其糖原磷酸化酶抑制活性
Pharmazie. 2010 Apr;65(4):235-8.
9
Primary amine/(+)-CSA salt-promoted organocatalytic conjugate addition of nitro esters to enones.伯胺/（+）-CSA 盐促进的硝基酯与烯酮的有机催化共轭加成。
Org Lett. 2010 May 21;12(10):2278-81. doi: 10.1021/ol1006407.
10
Chemoenzymatic synthesis of Amaryllidaceae constituents and biological evaluation of their C-1 analogues. The next generation synthesis of 7-deoxypancratistatin and trans-dihydrolycoricidine.酶促化学合成石蒜科成分及其 C-1 类似物的生物评价。7-去氧番荔枝碱和反式二氢血根碱的下一代合成。
J Org Chem. 2010 May 7;75(9):3069-84. doi: 10.1021/jo1003136.