4-amino-5-(furan-3-yl)-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine | 1252858-67-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: 4-amino-5-(furan-3-yl)-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: (2R,3R,4R,5R)-2-[4-amino-5-(3-furyl)pyrrolo[2,3-d]pyrimidin-7-yl]-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diol；(2R,3R,4R,5R)-2-[4-amino-5-(furan-3-yl)pyrrolo[2,3-d]pyrimidin-7-yl]-5-(hydroxymethyl)-3-methyloxolane-3,4-diol
• CAS: 1252858-67-5
• 化学式: C₁₆H₁₈N₄O₅
• 分子量: 346.343
• InChiKey: YQQFXEIMUZOIGF-QTDMDRALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5-碘-7-(2-C-甲基-beta-D-呋喃核糖基)-7H-吡咯并[2,3-d]嘧啶-4-胺 、 3-呋喃硼酸 在 trisodium tris(3-sulfophenyl)phosphine 、 palladium diacetate 、 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以59%的产率得到4-amino-5-(furan-3-yl)-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  Sugar-modified derivatives of cytostatic 7-(het)aryl-7-deazaadenosines: 2′-C-methylribonucleosides, 2′-deoxy-2′-fluoroarabinonucleosides, arabinonucleosides and 2′-deoxyribonucleosides

  摘要：

  A series of novel sugar-modified derivatives of cytostatic 7-hetaryl-7-deazaadenosines (2'-C-methylribonucleosides, 2'-deoxy-2'-fluoroarabinonucleosides, arabinonucleosides and 2'-deoxyribonucleosides) was prepared and screened for biological activity. The synthesis consisted of preparation of the corresponding sugar-modified 7-iodo-7-deazaadenine nucleosides and their aqueous-phase Suzuki-Miyaura cross-coupling reactions with (het)arylboronic acids or Stille couplings with hetarylstannanes in DMF. The synthesis of 7-iodo-7-deazaadenine nucleosides was based on a glycosidation of 6-chloro-7-iodo-7-deazapurine with a suitable sugar synthon or on an interconversion of 2'-OH stereocenter (for arabinonucleosides). Several examples of 2'-C-Me-ribonucleosides showed moderate anti-HCV activities in a replicon assay accompanied by cytotoxicity. Several 7-hetaryl-7-deazaadenine fluoroarabino-and arabinonucleosides exerted moderate micromolar cytostatic effects. The most active was 7-ethynyl-7-deazaadenine fluoroarabinonucleoside which showed submicromolar antiproliferative activity. However, all the sugar-modified derivatives were less active than the parent ribonucleosides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.003

文献信息

• NOVEL 7-DEAZAPURINE NUCLEOSIDES FOR THERAPEUTIC USES
  申请人：Bourderioux Aurelie

  公开号：US20150218201A1

  公开（公告）日：2015-08-06

  The invention provides compounds of formula I, wherein R1, R2 and R3 have values defined in the specification and a pharmaceutically acceptable salt thereof; or an optical isomer thereof; or a mixture of optical isomers, as well as compositions comprising such compounds and therapeutic methods that utilize such compounds and/or compositions.

  本发明提供了式子I的化合物，其中R1、R2和R3的值在规范中定义，并且其药学上可接受的盐；或其光学异构体；或其光学异构体的混合物，以及包含这些化合物的组合物和利用这些化合物和/或组合物的治疗方法。
• 7-deazapurine nucleosides for therapeutic uses
  申请人：Institute of Organic Chemistry and Biochemistry ASCR, V.V.I.

  公开号：US10294262B2

  公开（公告）日：2019-05-21

  The invention provides compounds of formula I, wherein R1, R2 and R3 have values defined in the specification and a pharmaceutically acceptable salt thereof; or an optical isomer thereof; or a mixture of optical isomers, as well as compositions comprising such compounds and therapeutic methods that utilize such compounds and/or compositions.

  本发明提供了式 I 的化合物（其中 R1、R2 和 R3 的值在说明书中定义）及其药学上可接受的盐；或其光学异构体；或光学异构体的混合物，以及包含此类化合物的组合物和利用此类化合物和/或组合物的治疗方法。
• US9321800B2
  申请人：——

  公开号：US9321800B2

  公开（公告）日：2016-04-26
• US9624257B2
  申请人：——

  公开号：US9624257B2

  公开（公告）日：2017-04-18
• Sugar-modified derivatives of cytostatic 7-(het)aryl-7-deazaadenosines: 2′-C-methylribonucleosides, 2′-deoxy-2′-fluoroarabinonucleosides, arabinonucleosides and 2′-deoxyribonucleosides
  作者：Petr Nauš、Pavla Perlíková、Aurelie Bourderioux、Radek Pohl、Lenka Slavětínská、Ivan Votruba、Gina Bahador、Gabriel Birkuš、Tomáš Cihlář、Michal Hocek

  DOI：10.1016/j.bmc.2012.07.003

  日期：2012.9

  A series of novel sugar-modified derivatives of cytostatic 7-hetaryl-7-deazaadenosines (2'-C-methylribonucleosides, 2'-deoxy-2'-fluoroarabinonucleosides, arabinonucleosides and 2'-deoxyribonucleosides) was prepared and screened for biological activity. The synthesis consisted of preparation of the corresponding sugar-modified 7-iodo-7-deazaadenine nucleosides and their aqueous-phase Suzuki-Miyaura cross-coupling reactions with (het)arylboronic acids or Stille couplings with hetarylstannanes in DMF. The synthesis of 7-iodo-7-deazaadenine nucleosides was based on a glycosidation of 6-chloro-7-iodo-7-deazapurine with a suitable sugar synthon or on an interconversion of 2'-OH stereocenter (for arabinonucleosides). Several examples of 2'-C-Me-ribonucleosides showed moderate anti-HCV activities in a replicon assay accompanied by cytotoxicity. Several 7-hetaryl-7-deazaadenine fluoroarabino-and arabinonucleosides exerted moderate micromolar cytostatic effects. The most active was 7-ethynyl-7-deazaadenine fluoroarabinonucleoside which showed submicromolar antiproliferative activity. However, all the sugar-modified derivatives were less active than the parent ribonucleosides. (C) 2012 Elsevier Ltd. All rights reserved.