• 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

通过温和的铜催化1-Bn-DHIQs串联氧化/芳构化实现的氧代阿朴菲生物碱的新型全合成。

Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs.

作者信息

Zheng Bo, Qu Hui-Ya, Meng Tian-Zhuo, Lu Xia, Zheng Jie, He Yun-Gang, Fan Qi-Qi, Shi Xiao-Xin

机构信息

Shanghai Key Laboratory of Chemical Biology and Department of Pharmaceutical Engineering, School of Pharmacy, East China University of Science and Technology 130 Mei-Long Road Shanghai 200237 P. R. China

出版信息

RSC Adv. 2018 Aug 14;8(51):28997-29007. doi: 10.1039/c8ra05338c.

DOI:10.1039/c8ra05338c
PMID:35548004
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9084380/
Abstract

Novel total syntheses of oxoaporphine alkaloids such as liriodenine, dicentrinone, cassameridine, lysicamine, oxoglaucine and -methylmoschatoline were developed. The key step of these total syntheses is Cu-catalyzed conversion of 1-benzyl-3,4-dihydro-isoquinolines (1-Bn-DHIQs) to 1-benzoyl-isoquinolines (1-Bz-IQs) tandem oxidation/aromatization. This novel Cu-catalyzed conversion has been studied in detail, and was successfully used for constructing the 1-Bz-IQ core.

摘要

开发了如鹅掌楸碱、双氢荷包牡丹碱、南美卡锡明、石蒜碱、氧化海罂粟碱和去甲异紫堇定等氧代阿朴啡生物碱的新型全合成方法。这些全合成的关键步骤是铜催化的1-苄基-3,4-二氢异喹啉（1-Bn-DHIQs）串联氧化/芳构化转化为1-苯甲酰基异喹啉（1-Bz-IQs）。这种新型的铜催化转化已得到详细研究，并成功用于构建1-Bz-IQ核心。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f27/9084380/fcc16a3c8ceb/c8ra05338c-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f27/9084380/f557f02c8a43/c8ra05338c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f27/9084380/24517d7f46ed/c8ra05338c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f27/9084380/a1a5647a20c8/c8ra05338c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f27/9084380/fcc16a3c8ceb/c8ra05338c-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f27/9084380/f557f02c8a43/c8ra05338c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f27/9084380/24517d7f46ed/c8ra05338c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f27/9084380/a1a5647a20c8/c8ra05338c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1f27/9084380/fcc16a3c8ceb/c8ra05338c-s3.jpg

相似文献

1
Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs.通过温和的铜催化1-Bn-DHIQs串联氧化/芳构化实现的氧代阿朴菲生物碱的新型全合成。
RSC Adv. 2018 Aug 14;8(51):28997-29007. doi: 10.1039/c8ra05338c.
2
Copper(ii)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp)-H bonds adjacent to 3,4-dihydroisoquinolines using air (O) as a clean oxidant.铜（II）催化且酸促进的，以空气（O）作为清洁氧化剂，对与3,4-二氢异喹啉相邻的可互变异构的C（sp）-H键进行高度区域选择性氧化反应。
RSC Adv. 2021 Sep 6;11(47):29702-29710. doi: 10.1039/d1ra05671a. eCollection 2021 Sep 1.
3
Isolation of bioactive and other oxoaporphine alkaloids from two annonaceous plants, Xylopia aethiopica and Miliusa cf. banacea.
J Nat Prod. 1994 Jan;57(1):68-73. doi: 10.1021/np50103a009.
4
Oxoaporphine alkaloids: conversion of lysicamine into liriodendronine and its 2-O-methyl ether, and antifungal activity.氧代阿朴啡生物碱：裂解胺转化为鹅掌楸碱及其2-O-甲基醚，以及抗真菌活性。
Arch Pharm (Weinheim). 1991 Jan;324(1):29-33. doi: 10.1002/ardp.19913240109.
5
A divergent approach to benzylisoquinoline-type and oxoaporphine alkaloids via regioselective direct ring metalation of alkoxy isoquinolines.通过烷氧基异喹啉的区域选择性直接环金属化反应合成苄基异喹啉类和氧代阿朴啡生物碱的一种发散式方法。
Org Biomol Chem. 2015 Jul 28;13(28):7664-72. doi: 10.1039/c5ob00926j.
6
Antimicrobial activity of benzylisoquinoline alkaloids.苄基异喹啉生物碱的抗菌活性。
Pharmazie. 1987 Apr;42(4):248-50.
7
Antibacterial and antifungal activity of liriodenine and related oxoaporphine alkaloids.莲叶桐碱及相关氧化阿朴菲生物碱的抗菌和抗真菌活性。
J Pharm Sci. 1980 Oct;69(10):1180-3. doi: 10.1002/jps.2600691016.
8
Oxoaporphine alkaloids and quinones from Stephania dinklagei and evaluation of their antiprotozoal activities.来自鼎湖地不容的氧代阿朴啡生物碱和醌类及其抗寄生虫活性评价
Planta Med. 2000 Jun;66(5):478-80. doi: 10.1055/s-2000-8597.
9
In vivo efficacy of antifungal oxoaporphine alkaloids in experimental disseminated candidiasis.
Pharm Res. 1987 Dec;4(6):495-8. doi: 10.1023/a:1016479622383.
10
Cu(II) catalyzed oxidation-[3+2] cycloaddition-aromatization cascade: efficient synthesis of pyrrolo [2, 1-a] isoquinolines.Cu(II) 催化氧化-[3+2]环加成-芳构化级联反应：吡咯并[2,1-a]异喹啉的高效合成。
Chem Commun (Camb). 2011 Jan 21;47(3):1036-8. doi: 10.1039/c0cc03186k. Epub 2010 Nov 12.

引用本文的文献

1
Biological Potential of Oxoglaucine in Medicine for the Treatment of Human Disorders: An Update on Pharmacological Activities and Related Molecular Mechanism.氧化青藤碱在治疗人类疾病医学中的生物学潜力：药理活性及相关分子机制的最新进展
Recent Adv Antiinfect Drug Discov. 2025;20(2):77-91. doi: 10.2174/0127724344297762240815073618.
2
Copper(ii)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp)-H bonds adjacent to 3,4-dihydroisoquinolines using air (O) as a clean oxidant.铜（II）催化且酸促进的，以空气（O）作为清洁氧化剂，对与3,4-二氢异喹啉相邻的可互变异构的C（sp）-H键进行高度区域选择性氧化反应。
RSC Adv. 2021 Sep 6;11(47):29702-29710. doi: 10.1039/d1ra05671a. eCollection 2021 Sep 1.

本文引用的文献

1
Anticancer effects of liriodenine on the cell growth and apoptosis of human breast cancer MCF-7 cells through the upregulation of p53 expression.去甲南天竹碱通过上调p53表达对人乳腺癌MCF-7细胞的生长和凋亡产生抗癌作用。
Oncol Lett. 2017 Aug;14(2):1979-1984. doi: 10.3892/ol.2017.6418. Epub 2017 Jun 19.
2
Antimicrobial photodynamic effect of extracts and oxoaporphine alkaloid isomoschatoline from Guatteria blepharophylla.来自睫毛瓜馥木的提取物和氧代阿朴啡生物碱异去甲乌药碱的抗菌光动力效应。
J Photochem Photobiol B. 2016 Jul;160:154-62. doi: 10.1016/j.jphotobiol.2016.04.010. Epub 2016 Apr 14.
3
Total Syntheses of Aporphine Alkaloids via Benzyne Chemistry: An Approach to the Formation of Aporphine Cores.
通过苯炔化学全合成阿朴菲生物碱：一种构建阿朴菲核心结构的方法。
J Org Chem. 2015 Oct 16;80(20):10033-40. doi: 10.1021/acs.joc.5b01634. Epub 2015 Sep 28.
4
A divergent approach to benzylisoquinoline-type and oxoaporphine alkaloids via regioselective direct ring metalation of alkoxy isoquinolines.通过烷氧基异喹啉的区域选择性直接环金属化反应合成苄基异喹啉类和氧代阿朴啡生物碱的一种发散式方法。
Org Biomol Chem. 2015 Jul 28;13(28):7664-72. doi: 10.1039/c5ob00926j.
5
Copper-Catalyzed Aerobic Oxidations of Organic Molecules: Pathways for Two-Electron Oxidation with a Four-Electron Oxidant and a One-Electron Redox-Active Catalyst.铜催化的有机分子有氧氧化反应：双电子氧化剂和单电子氧化还原活性催化剂的四电子氧化途径。
Acc Chem Res. 2015 Jun 16;48(6):1756-66. doi: 10.1021/acs.accounts.5b00060. Epub 2015 May 28.
6
Phosphatidylinositol 4-kinase III beta is the target of oxoglaucine and pachypodol (Ro 09-0179) for their anti-poliovirus activities, and is located at upstream of the target step of brefeldin A.磷脂酰肌醇4激酶IIIβ是氧化青霉菌素和厚叶木兰醇（Ro 09-0179）发挥抗脊髓灰质炎病毒活性的作用靶点，且位于布雷菲德菌素A作用靶点步骤的上游。
Microbiol Immunol. 2015 Jun;59(6):338-47. doi: 10.1111/1348-0421.12261.
7
Antibacterial alkaloids from Artabotrys crassifolius Hook.f. & Thomson.
Nat Prod Res. 2015;29(24):2346-9. doi: 10.1080/14786419.2015.1013954. Epub 2015 Mar 4.
8
Design, synthesis and anticancer activity of oxoaporphine alkaloid derivatives.设计、合成及氧桥阿朴啡类生物碱衍生物的抗癌活性。
J Enzyme Inhib Med Chem. 2014 Oct;29(5):722-7. doi: 10.3109/14756366.2013.845818. Epub 2014 Jun 25.
9
Aporphine alkaloids from the leaves of Phoebe grandis (Nees) Mer. (Lauraceae) and their cytotoxic and antibacterial activities.大乔木叶中的阿朴啡类生物碱及其细胞毒性和抗菌活性。
Molecules. 2013 Jul 29;18(8):8994-9009. doi: 10.3390/molecules18088994.
10
Aerobic copper-catalyzed organic reactions.需氧铜催化的有机反应。
Chem Rev. 2013 Aug 14;113(8):6234-458. doi: 10.1021/cr300527g. Epub 2013 Jun 20.