• 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

首次全合成天然存在的碘化 5'-脱氧木呋喃核苷。

First total synthesis of a naturally occurring iodinated 5'-deoxyxylofuranosyl marine nucleoside.

机构信息

Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science Technology Normal University, Nanchang 330013, China.

出版信息

Mar Drugs. 2012 Apr;10(4):881-889. doi: 10.3390/md10040881. Epub 2012 Apr 10.

DOI:10.3390/md10040881
PMID:22690148
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3366680/
Abstract

4-Amino-7-(5'-deoxy-β-D-xylofuranosyl)-5-iodo-pyrrolo[2,3-d]pyrimidine 1, an unusual naturally occurring marine nucleoside isolated from an ascidan, Diplosoma sp., was synthesized from D-xylose in seven steps with 28% overall yield on 10 g scale. The key step was Vorbrüggen glycosylation of 5-iodo-pyrrolo[2,3-d]pyrimidine with 5-deoxy-1,2-O-diacetyl-3-O-benzoyl-D-xylofuranose. Its absolute configuration was confirmed.

摘要

4-氨基-7-(5'-脱氧-β-D-木呋喃糖基)-5-碘代吡咯并[2,3-d]嘧啶核苷 1 是一种从 ascidan Diplosoma sp. 中分离得到的非寻常的天然海洋核苷，可由 D-木糖经七步反应、以 10 g 规模计总收率 28%合成得到。关键步骤是 5-碘代吡咯并[2,3-d]嘧啶核苷与 5-脱氧-1,2-O-二乙酰基-3-O-苯甲酰基-D-木呋喃糖的 Vorbrüggen 糖苷化反应。其绝对构型得到了确证。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f864/3366680/6e81a81b14f9/marinedrugs-10-00881-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f864/3366680/acdd505ca906/marinedrugs-10-00881-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f864/3366680/6e81a81b14f9/marinedrugs-10-00881-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f864/3366680/acdd505ca906/marinedrugs-10-00881-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f864/3366680/6e81a81b14f9/marinedrugs-10-00881-g002.jpg

相似文献

1
First total synthesis of a naturally occurring iodinated 5'-deoxyxylofuranosyl marine nucleoside.首次全合成天然存在的碘化 5'-脱氧木呋喃核苷。
Mar Drugs. 2012 Apr;10(4):881-889. doi: 10.3390/md10040881. Epub 2012 Apr 10.
2
Total Synthesis of Mycalisine B.麦角新碱 B 的全合成。
Mar Drugs. 2019 Apr 14;17(4):226. doi: 10.3390/md17040226.
3
An Expeditious Total Synthesis of 5'-Deoxy-toyocamycin and 5'-Deoxysangivamycin.5'-脱氧土霉素和 5'-脱氧桑吉霉素的快速全合成。
Molecules. 2019 Feb 19;24(4):737. doi: 10.3390/molecules24040737.
4
An efficient synthesis of 3-fluoro-5-thio-xylofuranosyl nucleosides of thymine, uracil, and 5-fluorouracil as potential antitumor or/and antiviral agents.作为潜在抗肿瘤和/或抗病毒药物的胸腺嘧啶、尿嘧啶和5-氟尿嘧啶的3-氟-5-硫代木糖呋喃糖基核苷的高效合成。
Bioorg Med Chem. 2007 May 1;15(9):3241-7. doi: 10.1016/j.bmc.2007.02.031. Epub 2007 Feb 20.
5
Systematic synthesis and biological evaluation of alpha- and beta-D-xylofuranosyl nucleosides of the five naturally occurring bases in nucleic acids and related analogues.核酸中五种天然存在碱基的α-和β-D-呋喃木糖基核苷及其相关类似物的系统合成与生物学评价。
J Med Chem. 1986 Feb;29(2):203-13. doi: 10.1021/jm00152a007.
6
6-Methylpurine derived sugar modified nucleosides: Synthesis and evaluation of their substrate activity with purine nucleoside phosphorylases.6-甲基嘌呤衍生的糖修饰核苷：其与嘌呤核苷磷酸化酶底物活性的合成及评估
Bioorg Chem. 2016 Apr;65:9-16. doi: 10.1016/j.bioorg.2015.12.006. Epub 2015 Dec 24.
7
1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-L-erythro-pentofuran ose, a convenient precursor for the stereospecific synthesis of nucleoside analogues with the unnatural beta-L-configuration.1,2-二-O-乙酰基-5-O-苯甲酰基-3-脱氧-L-赤藓糖戊呋喃糖，一种用于立体定向合成具有非天然β-L-构型核苷类似物的便捷前体。
Carbohydr Res. 2000 Jan 12;323(1-4):226-9. doi: 10.1016/s0008-6215(99)00267-0.
8
Synthesis and anti-DNA viral activities in vitro of certain 2,4-disubstituted-7-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)pyrrolo[2,3-d d pyrimidine nucleosides.某些2,4-二取代-7-(2-脱氧-2-氟-β-D-阿拉伯呋喃糖基)吡咯并[2,3-d]嘧啶核苷的体外合成及其抗DNA病毒活性
J Med Chem. 1995 Sep 29;38(20):3957-66. doi: 10.1021/jm00020a009.
9
Marine natural products.海洋天然产物。
Nat Prod Rep. 2020 Feb 26;37(2):175-223. doi: 10.1039/c9np00069k.
10
Pyrrolopyrimidine nucleosides. 18. Synthesis and chemotherapeutic activity of 4-amino-7-(3-deoxy-beta-D-ribofuranosyl)pyrrolo[2,3-d] pyrimidine-5-carboxamide (3'-deoxysangivamycin) and 4-amino-7-(2-deoxy-beta-D-ribofuranosyl)pyrrolo[2,3-d] pyrimidine-5-carboxamide (2'-deoxysangivamycin).吡咯并嘧啶核苷。18. 4-氨基-7-(3-脱氧-β-D-呋喃核糖基)吡咯并[2,3-d]嘧啶-5-甲酰胺（3'-脱氧杀结核菌素）和4-氨基-7-(2-脱氧-β-D-呋喃核糖基)吡咯并[2,3-d]嘧啶-5-甲酰胺（2'-脱氧杀结核菌素）的合成及化疗活性
J Med Chem. 1983 Jan;26(1):25-9. doi: 10.1021/jm00355a006.

引用本文的文献

1
First Total Synthesis of 5'--α-d-Glucopyranosyl Tubercidin.首次全合成 5'-α-d-葡萄糖基紫菀苷。
Mar Drugs. 2020 Jul 29;18(8):398. doi: 10.3390/md18080398.
2
Total Synthesis of Mycalisine B.麦角新碱 B 的全合成。
Mar Drugs. 2019 Apr 14;17(4):226. doi: 10.3390/md17040226.
3
An Expeditious Total Synthesis of 5'-Deoxy-toyocamycin and 5'-Deoxysangivamycin.5'-脱氧土霉素和 5'-脱氧桑吉霉素的快速全合成。

本文引用的文献

1
Deoxyuridines from the marine sponge associated actinomycete Streptomyces microflavus.海洋海绵共生放线菌小孢链霉菌中的脱氧尿苷。
Mar Drugs. 2011;9(5):690-695. doi: 10.3390/md9050690. Epub 2011 Apr 26.
2
Antiviral lead compounds from marine sponges.海洋海绵中的抗病毒先导化合物。
Mar Drugs. 2010 Oct 11;8(10):2619-38. doi: 10.3390/md8102619.
3
ARC (NSC 188491) has identical activity to Sangivamycin (NSC 65346) including inhibition of both P-TEFb and PKC.ARC（NSC 188491）与桑吉瓦霉素（NSC 65346）具有相同的活性，包括对P-TEFb和蛋白激酶C的抑制作用。
Molecules. 2019 Feb 19;24(4):737. doi: 10.3390/molecules24040737.
4
First total synthesis of kipukasin A.基普卡辛A的首次全合成。
Beilstein J Org Chem. 2017 May 9;13:855-862. doi: 10.3762/bjoc.13.86. eCollection 2017.
5
An Expedient Total Synthesis of Triciribine.曲西立滨的便捷全合成
Molecules. 2017 Apr 17;22(4):643. doi: 10.3390/molecules22040643.
6
Concise total synthesis of two marine natural nucleosides: trachycladines A and B.两种海洋天然核苷：特拉奇拉定 A 和 B 的简洁全合成。
Beilstein J Org Chem. 2014 Jul 24;10:1681-5. doi: 10.3762/bjoc.10.176. eCollection 2014.
7
Total synthesis of a marine alkaloid--rigidin E.海洋生物碱——瑞格列汀 E 的全合成。
Mar Drugs. 2012 Jun;10(6):1412-1421. doi: 10.3390/md10061412. Epub 2012 Jun 20.
BMC Cancer. 2009 Feb 20;9:63. doi: 10.1186/1471-2407-9-63.
4
Toyocamycin specifically inhibits auxin signaling mediated by SCFTIR1 pathway.丰加霉素特异性抑制由SCFTIR1途径介导的生长素信号传导。
Phytochemistry. 2009 Jan;70(2):190-7. doi: 10.1016/j.phytochem.2008.12.020. Epub 2009 Jan 24.
5
Xanthine oxidase-activated prodrugs of thymidine phosphorylase inhibitors.胸苷磷酸化酶抑制剂的黄嘌呤氧化酶激活前药。
Eur J Med Chem. 2008 Jun;43(6):1248-60. doi: 10.1016/j.ejmech.2007.07.015. Epub 2007 Aug 6.
6
7-Functionalized 7-deazapurine ribonucleosides related to 2-aminoadenosine, guanosine, and xanthosine: glycosylation of pyrrolo[2,3-d]pyrimidines with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose.与2-氨基腺苷、鸟苷和黄苷相关的7-官能化7-脱氮嘌呤核糖核苷：吡咯并[2,3-d]嘧啶与1-O-乙酰基-2,3,5-三-O-苯甲酰基-D-呋喃核糖的糖基化反应
J Org Chem. 2006 Jan 6;71(1):81-90. doi: 10.1021/jo0516640.
7
Synthesis and enzymatic evaluation of xanthine oxidase-activated prodrugs based on inhibitors of thymidine phosphorylase.基于胸苷磷酸化酶抑制剂的黄嘌呤氧化酶激活前药的合成及酶学评价
Bioorg Med Chem Lett. 2004 Nov 1;14(21):5247-50. doi: 10.1016/j.bmcl.2004.08.036.
8
Practical synthesis of a potent hepatitis C virus RNA replication inhibitor.一种强效丙型肝炎病毒RNA复制抑制剂的实用合成方法。
J Org Chem. 2004 Sep 17;69(19):6257-66. doi: 10.1021/jo0491096.
9
TUBERCIDIN.杀结核菌素
Cancer Chemother Rep. 1963 Jul;30:61-2.
10
1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-L-erythro-pentofuran ose, a convenient precursor for the stereospecific synthesis of nucleoside analogues with the unnatural beta-L-configuration.1,2-二-O-乙酰基-5-O-苯甲酰基-3-脱氧-L-赤藓糖戊呋喃糖，一种用于立体定向合成具有非天然β-L-构型核苷类似物的便捷前体。
Carbohydr Res. 2000 Jan 12;323(1-4):226-9. doi: 10.1016/s0008-6215(99)00267-0.