• 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

相似文献

1
2'-Deoxy-3,7-dideazaguanosine and related compounds. Synthesis of 6-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl) and 1-beta-D-arabinofuranosyl-1H-pyrrolo[3,2-c]pyridin-4(5H)-one via direct glycosylation of a pyrrole precursor.2'-脱氧-3,7-二脱氮鸟苷及相关化合物。通过吡咯前体的直接糖基化反应合成6-氨基-1-(2-脱氧-β-D-赤型-戊呋喃糖基)和1-β-D-阿拉伯呋喃糖基-1H-吡咯并[3,2-c]吡啶-4(5H)-酮。
Nucleic Acids Res. 1987 Feb 11;15(3):1217-26. doi: 10.1093/nar/15.3.1217.
2
Synthesis and antiproliferative and antiviral activity of carbohydrate-modified pyrrolo[2,3-d]pyridazin-7-one nucleosides.碳水化合物修饰的吡咯并[2,3-d]哒嗪-7-酮核苷的合成及其抗增殖和抗病毒活性
J Med Chem. 1997 Feb 28;40(5):794-801. doi: 10.1021/jm960631x.
3
Synthesis and biological activity of certain 6-substituted and 2,6-disubstituted 2'-deoxytubercidins prepared via the stereospecific sodium salt glycosylation procedure.通过立体定向钠盐糖基化方法制备的某些6-取代和2,6-二取代2'-脱氧结核菌素的合成及生物活性
J Med Chem. 1985 Oct;28(10):1461-7. doi: 10.1021/jm00148a015.
4
A new synthesis of certain 7-(beta-D-ribofuranosyl) and 7-(2-deoxy-beta-D-ribofuranosyl) derivatives of 3-deazaguanine via the sodium salt glycosylation procedure.通过钠盐糖基化方法对某些3-脱氮鸟嘌呤的7-（β-D-呋喃核糖基）和7-（2-脱氧-β-D-呋喃核糖基）衍生物进行新的合成。
Nucleic Acids Res. 1985 Jul 25;13(14):5341-52. doi: 10.1093/nar/13.14.5341.
5
Synthesis of 4- and 5-amino-1-(2-deoxy-D-erythro-pentofuranosyl)imidazole nucleosides by chemical and biotransformation methods.通过化学和生物转化方法合成4-氨基和5-氨基-1-(2-脱氧-D-赤藓糖基)咪唑核苷
Carbohydr Res. 1991 Sep 2;216:109-18. doi: 10.1016/0008-6215(92)84154-k.
6
Synthesis of a novel C-nucleoside, 2-amino-7-(2-deoxy-beta-D-erythro- pentofuranosyl)-3H,5H-pyrrolo-[3,2-d]pyrimidin-4-one (2'-deoxy-9-deazaguanosine).
Nucleosides Nucleotides. 1999 Mar;18(3):363-76. doi: 10.1080/15257779908043082.
7
Synthesis and biological evaluation of certain 2'-deoxy-beta-D-ribo- and -beta-D-arabinofuranosyl nucleosides of purine-6-carboxamide and 4,8-diaminopyrimido[5,4-d]pyrimidine.嘌呤 -6- 甲酰胺及 4,8- 二氨基嘧啶并 [5,4-d] 嘧啶的某些 2'- 脱氧 -β-D- 核糖呋喃糖基和 -β-D- 阿拉伯呋喃糖基核苷的合成与生物学评价
J Med Chem. 1981 Apr;24(4):393-8. doi: 10.1021/jm00136a008.
8
Synthesis and antitumor activity of fluorine-substituted 4-amino-2(1H)-pyridinones and their nucleosides. 3-Deazacytosines.
J Med Chem. 1987 Feb;30(2):340-7. doi: 10.1021/jm00385a016.
9
Halogenated 7-deazapurine nucleosides: stereoselective synthesis and conformation of 2'-deoxy-2'-fluoro-beta-D-arabinonucleosides.卤代7-脱氮嘌呤核苷：2'-脱氧-2'-氟-β-D-阿拉伯核苷的立体选择性合成与构象
Org Biomol Chem. 2004 Oct 7;2(19):2838-46. doi: 10.1039/B409648G. Epub 2004 Sep 9.
10
3-Bromopyrazolo[3,4-d]pyrimidine 2'-deoxy-2'-fluoro-beta-D-arabinonucleosides: modified DNA constituents with an unusually rigid sugar N-conformation.3-溴吡唑并[3,4-d]嘧啶2'-脱氧-2'-氟-β-D-阿拉伯核苷：具有异常刚性糖N-构象的修饰DNA成分。
J Org Chem. 2003 Jul 11;68(14):5519-24. doi: 10.1021/jo030051p.

本文引用的文献

1
Synthesis and antiviral/antitumor activities of certain 3-deazaguanine nucleosides and nucleotides.某些3-脱氮鸟嘌呤核苷和核苷酸的合成及其抗病毒/抗肿瘤活性
J Med Chem. 1984 Nov;27(11):1389-96. doi: 10.1021/jm00377a002.
2
Glycosylindoles. VII. Synthesis of 1-(D-beta-ribofuranosyl)indole.糖基吲哚。VII。1-(D-β-呋喃核糖基)吲哚的合成。
Tetrahedron. 1967 Dec;23(12):4653-60. doi: 10.1016/s0040-4020(01)92563-3.
3
Purine nucleosides. XI. The synthesis of 2'-deoxy-9-alpha- and-beta-D-ribofuranosylpurines and the correlation of their anomeric structure with proton magnetic resonance spectra.嘌呤核苷。XI. 2'-脱氧-9-α-和-β-D-呋喃核糖基嘌呤的合成及其异头结构与质子磁共振谱的相关性。
J Am Chem Soc. 1965 Nov 5;87(21):4934-40. doi: 10.1021/ja00949a042.
4
Indole and 4-aminoindole nucleosides.吲哚和4-氨基吲哚核苷。
J Org Chem. 1968 Jan;33(1):192-7. doi: 10.1021/jo01265a602.
5
Synthesis and biological activity of certain 6-substituted and 2,6-disubstituted 2'-deoxytubercidins prepared via the stereospecific sodium salt glycosylation procedure.通过立体定向钠盐糖基化方法制备的某些6-取代和2,6-二取代2'-脱氧结核菌素的合成及生物活性
J Med Chem. 1985 Oct;28(10):1461-7. doi: 10.1021/jm00148a015.
6
Synthesis and xanthine oxidase inhibitory analysis of 1H-pyrrolo[3,2-c]pyridine-4,6(5H,7H)-dione (3,7-dideazaxanthine) and two of its derivatives.1H-吡咯并[3,2-c]吡啶-4,6(5H,7H)-二酮（3,7-二脱氮黄嘌呤）及其两种衍生物的合成与黄嘌呤氧化酶抑制分析
J Med Chem. 1978 Sep;21(9):990-3. doi: 10.1021/jm00207a028.

2'-脱氧-3,7-二脱氮鸟苷及相关化合物。通过吡咯前体的直接糖基化反应合成6-氨基-1-(2-脱氧-β-D-赤型-戊呋喃糖基)和1-β-D-阿拉伯呋喃糖基-1H-吡咯并[3,2-c]吡啶-4(5H)-酮。

2'-Deoxy-3,7-dideazaguanosine and related compounds. Synthesis of 6-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl) and 1-beta-D-arabinofuranosyl-1H-pyrrolo[3,2-c]pyridin-4(5H)-one via direct glycosylation of a pyrrole precursor.

作者信息

Girgis N S, Cottam H B, Larson S B, Robins R K

出版信息

Nucleic Acids Res. 1987 Feb 11;15(3):1217-26. doi: 10.1093/nar/15.3.1217.

DOI:10.1093/nar/15.3.1217
PMID:3593477
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC340519/
Abstract

The synthesis of two new analogs of 2'-deoxyguanosine, 6-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-1H-pyrrolo[3,2-c] pyridin-4(5H)-one (8) and 6-amino-1-beta-D-arabinofuranosyl-1H-pyrrolo[3,2-c]-pyridin-4(5H)-one (13) has been accomplished by glycosylation of the sodium salt of ethyl 2-cyanomethyl-1H-pyrrole-3-carboxylate (4c) using 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-alpha-D-erythro-pentofuranose( 5) and 1-chloro-2,3,5-tri-O-benzyl-alpha-D-arabinofuranose (9), respectively. The resulting blocked nucleosides, ethyl 2-cyanomethyl-1-(2-deoxy-3,5-di-O-p-toluoyl-beta-D-erythro- pentofuranosyl)-1H-pyrrole-3-carboxylate (6) and ethyl 2-cyanomethyl-1-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)- 1H-pyrrole-3-carboxylate, were ring closed with hydrazine to form 5-amino-6-hydrazino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-1H- pyrrolo[3,2-c]-pyridin-4(5H)-one (7) and 5,6-diamino-1-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)-1H- pyrrolo[3,2-c]pyridin-4(5H)-one (11), respectively. Treatment of 7 with Raney nickel provided the 2'-deoxyguanosine analog 8 while reaction of 11 with Raney nickel followed by palladium hydroxide/cyclohexene treatment gave the 2'-deoxyguanosine analog 13. The anomeric configuration of 8 was assigned as beta by proton NMR, while that of 13 was confirmed as beta by single-crystal X-ray analysis of the deblocked precursor ethyl 2-cyanomethyl-1-beta-D-arabinofuranosyl-1H-pyrrole-3-carboxylate (10a).

摘要

通过分别使用1-氯-2-脱氧-3,5-二-O-对甲苯甲酰基-α-D-赤藓戊呋喃糖（5）和1-氯-2,3,5-三-O-苄基-α-D-阿拉伯呋喃糖（9）对2-氰基甲基-1H-吡咯-3-羧酸乙酯（4c）的钠盐进行糖基化反应，合成了两种新的2'-脱氧鸟苷类似物，即6-氨基-1-（2-脱氧-β-D-赤藓戊呋喃糖基）-1H-吡咯并[3,2-c]吡啶-4（5H）-酮（8）和(6-氨基-1-β-D-阿拉伯呋喃糖基-1H-吡咯并[3,2-c]吡啶-4(5H)-酮(13))。得到的受阻核苷，即2-氰基甲基-1-（2-脱氧-3,5-二-O-对甲苯甲酰基-β-D-赤藓戊呋喃糖基）-1H-吡咯-3-羧酸乙酯（6）和2-氰基甲基-1-（2,3,5-三-O-苄基-β-D-阿拉伯呋喃糖基）-1H-吡咯-3-羧酸乙酯，用肼进行闭环反应，分别形成5-氨基-6-肼基-1-（2-脱氧-β-D-赤藓戊呋喃糖基）- (1H-吡咯并[3,2-c]吡啶-4(5H)-酮(7))和5,6-二氨基-1-（2,3,5-三-O-苄基-β-D-阿拉伯呋喃糖基）-1H-吡咯并[3,2-c]吡啶-4（5H）-酮（11）。用雷尼镍处理7得到2'-脱氧鸟苷类似物8，而11与雷尼镍反应，然后用氢氧化钯/环己烯处理得到2'-脱氧鸟苷类似物13。通过质子核磁共振将8的异头构型指定为β，而通过对去保护的前体2-氰基甲基-1-β-D-阿拉伯呋喃糖基-1H-吡咯-3-羧酸乙酯（10a）的单晶X射线分析确认13的异头构型为β。