• 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

吡啶并稠合脱氮嘌呤碱基：4-取代的9-吡啶并[2',3':4,5]-和吡啶并[4',3':4,5]吡咯并[2,3-]嘧啶的合成与糖基化

Pyrido-Fused Deazapurine Bases: Synthesis and Glycosylation of 4-Substituted 9-Pyrido[2',3':4,5]- and Pyrido[4',3':4,5]pyrrolo[2,3-]pyrimidines.

作者信息

Veselovská Lucia, Pohl Radek, Tloušt Ová Eva, Gurská Soňa, Džubák Petr, Hajdúch Marián, Hocek Michal

机构信息

Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nam. 2, CZ-16610 Prague 6, Czech Republic.

Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacky University and University Hospital in Olomouc, Hnìvotínská 5, CZ-77515 Olomouc, Czech Republic.

出版信息

ACS Omega. 2020 Oct 2;5(40):26278-26286. doi: 10.1021/acsomega.0c04302. eCollection 2020 Oct 13.

DOI:10.1021/acsomega.0c04302
PMID:33073155
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7557996/
Abstract

Two isomeric sets of 4-substituted pyridopyrrolopyrimidine nucleobases were prepared through nucleophilic substitutions or cross-coupling reactions of 4-chloropyridopyrrolopyrimidines. The corresponding 4-amino-pyridopyrrolopyrimidines were glycosylated with 5--tritylribose using the modified Mitsunobu protocol. Several examples of the title heterocycles showed blue or green fluorescence. Testing of the pyridopyrrolopyrimidine nucleobases for the cytotoxic effect revealed micromolar activity of 4-benzofuryl derivatives in both series, preferentially in multidrug-resistant cancers.

摘要

通过4-氯代吡啶并吡咯并嘧啶的亲核取代或交叉偶联反应制备了两组4-取代吡啶并吡咯并嘧啶核碱基的异构体。使用改良的 Mitsunobu 方法，相应的4-氨基吡啶并吡咯并嘧啶与5-O-三苯甲基核糖进行糖基化反应。几个标题杂环化合物的例子显示出蓝色或绿色荧光。对吡啶并吡咯并嘧啶核碱基的细胞毒性作用测试表明，两个系列中的4-苯并呋喃基衍生物均具有微摩尔活性，在多药耐药性癌症中活性更高。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82cb/7557996/dee5bdc2fd80/ao0c04302_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82cb/7557996/fbcd4c27f3a7/ao0c04302_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82cb/7557996/3c93e2070abe/ao0c04302_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82cb/7557996/004439564fcb/ao0c04302_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82cb/7557996/51e09719ea29/ao0c04302_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82cb/7557996/dee5bdc2fd80/ao0c04302_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82cb/7557996/fbcd4c27f3a7/ao0c04302_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82cb/7557996/3c93e2070abe/ao0c04302_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82cb/7557996/004439564fcb/ao0c04302_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82cb/7557996/51e09719ea29/ao0c04302_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82cb/7557996/dee5bdc2fd80/ao0c04302_0003.jpg

相似文献

1
Pyrido-Fused Deazapurine Bases: Synthesis and Glycosylation of 4-Substituted 9-Pyrido[2',3':4,5]- and Pyrido[4',3':4,5]pyrrolo[2,3-]pyrimidines.吡啶并稠合脱氮嘌呤碱基：4-取代的9-吡啶并[2',3':4,5]-和吡啶并[4',3':4,5]吡咯并[2,3-]嘧啶的合成与糖基化
ACS Omega. 2020 Oct 2;5(40):26278-26286. doi: 10.1021/acsomega.0c04302. eCollection 2020 Oct 13.
2
Synthesis and Cytotoxic and Antiviral Activity Profiling of All-Four Isomeric Series of Pyrido-Fused 7-Deazapurine Ribonucleosides.合成及全四种异构系列吡啶并稠合 7-脱氮嘌呤核苷的细胞毒性和抗病毒活性分析。
Chemistry. 2020 Oct 9;26(57):13002-13015. doi: 10.1002/chem.202001124. Epub 2020 Sep 16.
3
Synthesis of Polycyclic Hetero-Fused 7-Deazapurine Heterocycles and Nucleosides through C-H Dibenzothiophenation and Negishi Coupling.通过 C-H 二苯并噻吩化和 Negishi 偶联合成多环杂环稠合 7-去氮杂嘌呤杂环和核苷
J Am Chem Soc. 2022 Oct 26;144(42):19437-19446. doi: 10.1021/jacs.2c07517. Epub 2022 Oct 16.
4
Synthesis and Cytostatic and Antiviral Profiling of Thieno-Fused 7-Deazapurine Ribonucleosides.噻吩并稠合7-脱氮嘌呤核糖核苷的合成及其细胞抑制和抗病毒活性分析
J Med Chem. 2017 Mar 23;60(6):2411-2424. doi: 10.1021/acs.jmedchem.6b01766. Epub 2017 Mar 3.
5
Synthesis and Cytotoxic and Antiviral Profiling of Pyrrolo- and Furo-Fused 7-Deazapurine Ribonucleosides.吡咯并[2,3-d]嘧啶核苷和呋喃并[2,3-d]嘧啶核苷的合成及细胞毒性和抗病毒特性分析。
J Med Chem. 2018 Oct 25;61(20):9347-9359. doi: 10.1021/acs.jmedchem.8b01258. Epub 2018 Oct 16.
6
Synthesis, Photophysical Properties, and Biological Profiling of Benzothieno-Fused 7-Deazapurine Ribonucleosides.苯并噻吩并 7-去氮杂嘌呤核苷的合成、光物理性质和生物学分析。
J Org Chem. 2020 Jun 19;85(12):8085-8101. doi: 10.1021/acs.joc.0c00927. Epub 2020 Jun 4.
7
Synthesis and Biological Profiling of Pyrazolo-Fused 7-Deazapurine Nucleosides.吡唑并融合 7-脱氮嘌呤核苷的合成及生物学特性分析。
J Org Chem. 2020 Aug 21;85(16):10539-10551. doi: 10.1021/acs.joc.0c00928. Epub 2020 Aug 6.
8
Tyrosine kinase inhibitors. 10. Isomeric 4-[(3-bromophenyl)amino]pyrido[d]-pyrimidines are potent ATP binding site inhibitors of the tyrosine kinase function of the epidermal growth factor receptor.酪氨酸激酶抑制剂。10. 异构的4-[(3-溴苯基)氨基]吡啶并[d]嘧啶是表皮生长因子受体酪氨酸激酶功能的强效ATP结合位点抑制剂。
J Med Chem. 1996 Apr 26;39(9):1823-35. doi: 10.1021/jm9508651.
9
Synthesis and evaluation of 4-amino-substituted 7-methoxy (and 7-hydroxy)- 11-methyl (and 5,11-dimethyl)-10H-pyrido [2,3-b] carbazoles and 4-amino- substituted 11-methyl (and 5,11-dimethyl)-10H-pyrido[3',4':4,5] pyrrolo [3,2-g] quinolines, two new series related to antitumor ellipticine derivatives.4-氨基取代的7-甲氧基（及7-羟基）-11-甲基（及5,11-二甲基）-10H-吡啶并[2,3-b]咔唑和4-氨基取代的11-甲基（及5,11-二甲基）-10H-吡啶并[3',4':4,5]吡咯并[3,2-g]喹啉的合成与评价，这是两个与抗肿瘤椭圆玫瑰树碱衍生物相关的新系列。
Anticancer Drug Des. 1993 Dec;8(6):399-416.
10
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.

本文引用的文献

1
Synthesis and Biological Profiling of Pyrazolo-Fused 7-Deazapurine Nucleosides.吡唑并融合 7-脱氮嘌呤核苷的合成及生物学特性分析。
J Org Chem. 2020 Aug 21;85(16):10539-10551. doi: 10.1021/acs.joc.0c00928. Epub 2020 Aug 6.
2
Synthesis and Cytotoxic and Antiviral Activity Profiling of All-Four Isomeric Series of Pyrido-Fused 7-Deazapurine Ribonucleosides.合成及全四种异构系列吡啶并稠合 7-脱氮嘌呤核苷的细胞毒性和抗病毒活性分析。
Chemistry. 2020 Oct 9;26(57):13002-13015. doi: 10.1002/chem.202001124. Epub 2020 Sep 16.
3
Synthesis and Cytotoxic and Antiviral Profiling of Pyrrolo- and Furo-Fused 7-Deazapurine Ribonucleosides.
吡咯并[2,3-d]嘧啶核苷和呋喃并[2,3-d]嘧啶核苷的合成及细胞毒性和抗病毒特性分析。
J Med Chem. 2018 Oct 25;61(20):9347-9359. doi: 10.1021/acs.jmedchem.8b01258. Epub 2018 Oct 16.
4
Pyrrolo[2,3-d]pyrimidine (7-deazapurine) as a privileged scaffold in design of antitumor and antiviral nucleosides.吡咯并[2,3-d]嘧啶（7-脱氮嘌呤）作为抗肿瘤和抗病毒核苷设计中的优势骨架。
Med Res Rev. 2017 Nov;37(6):1429-1460. doi: 10.1002/med.21465. Epub 2017 Aug 23.
5
Discovery of novel substituted benzo-anellated 4-benzylamino pyrrolopyrimidines as dual EGFR and VEGFR2 inhibitors.新型取代苯并稠合4-苄基氨基吡咯并嘧啶作为双效表皮生长因子受体（EGFR）和血管内皮生长因子受体2（VEGFR2）抑制剂的发现
Bioorg Med Chem Lett. 2017 Jun 15;27(12):2708-2712. doi: 10.1016/j.bmcl.2017.04.053. Epub 2017 Apr 19.
6
Structure-Based Discovery of 4-(6-Methoxy-2-methyl-4-(quinolin-4-yl)-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole (CD161) as a Potent and Orally Bioavailable BET Bromodomain Inhibitor.基于结构发现4-(6-甲氧基-2-甲基-4-(喹啉-4-基)-9H-嘧啶并[4,5-b]吲哚-7-基)-3,5-二甲基异恶唑(CD161)作为一种强效且口服生物可利用的BET溴结构域抑制剂。
J Med Chem. 2017 May 11;60(9):3887-3901. doi: 10.1021/acs.jmedchem.7b00193. Epub 2017 May 2.
7
Synthesis and evaluation of 5-(arylthio)-9H-pyrimido[4,5-b]indole-2,4-diamines as receptor tyrosine kinase and thymidylate synthase inhibitors and as antitumor agents.5-（芳硫基）-9H-嘧啶并[4,5-b]吲哚-2,4-二胺作为受体酪氨酸激酶和胸苷酸合成酶抑制剂及抗肿瘤药物的合成与评价
Bioorg Med Chem Lett. 2017 Apr 1;27(7):1602-1607. doi: 10.1016/j.bmcl.2017.02.018. Epub 2017 Feb 11.
8
Synthesis and Cytostatic and Antiviral Profiling of Thieno-Fused 7-Deazapurine Ribonucleosides.噻吩并稠合7-脱氮嘌呤核糖核苷的合成及其细胞抑制和抗病毒活性分析
J Med Chem. 2017 Mar 23;60(6):2411-2424. doi: 10.1021/acs.jmedchem.6b01766. Epub 2017 Mar 3.
9
Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5-O-Monoprotected or 5-Modified Ribose: Improved Protocol, Scope, and Mechanism.通过核苷碱基与5-O-单保护或5-修饰核糖的直接糖基化反应合成核苷：改进的方案、范围及机理
Chemistry. 2017 Mar 17;23(16):3910-3917. doi: 10.1002/chem.201604955. Epub 2017 Feb 15.
10
Janus Compounds, 5-Chloro-N⁴-methyl-N⁴-aryl-9H-pyrimido[4,5-b]indole-2,4-diamines, Cause Both Microtubule Depolymerizing and Stabilizing Effects.Janus化合物，5-氯-N⁴-甲基-N⁴-芳基-9H-嘧啶并[4,5-b]吲哚-2,4-二胺，兼具微管解聚和稳定作用。
Molecules. 2016 Dec 2;21(12):1661. doi: 10.3390/molecules21121661.