4-amino-5-iodo-7-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine | 1393605-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 4-amino-5-iodo-7-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: (2R,3R,4S,5R)-5-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol；4-Amino-5-iodo-7-(2-deoxy-2-fluoro-beta-D-arabino furanosyl)-7H-pyrrolo[2.3-d]pyrimidine；(2R,3R,4S,5R)-5-(4-amino-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol
• CAS: 1393605-18-9
• 化学式: C₁₁H₁₂FIN₄O₃
• 分子量: 394.144
• InChiKey: WYSCBUKBHNIZLJ-GZCUOZMLSA-N

物化性质

• 沸点：
  659.1±55.0 °C(Predicted)
• 密度：
  2.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-amino-5-iodo-7-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 (2R,3R,4S,5R)-5-(4-amino-5-ethynyl-pyrrolo[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol
  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
• 作为产物：
  描述：

  4-chloro-5-iodo-7-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 在 ammonium hydroxide 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以84%的产率得到4-amino-5-iodo-7-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-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 PHOSPHATE ESTER COMPOUND HAVING PYRROLOPYRIMIDINE SKELETON OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF
  申请人：Taiho Pharmaceutical Co., Ltd.

  公开号：EP3988173A1

  公开（公告）日：2022-04-27

  There is provided a novel phosphate ester compound having a pyrrolopyrimidine skeleton having an excellent antitumor effect or a pharmaceutically acceptable salt thereof, and a method for preventing and/or treating a tumor in combination with an alkylating agent and/or a radiation therapy. According to one aspect of the present invention, there is provided a compound represented by the following general formula (1) or a pharmaceutically acceptable salt thereof, and a method for preventing and/or treating a tumor in combination with an alkylating agent and/or a radiation therapy.

  提供了一种具有优异抗肿瘤作用的新型磷酸酯化合物，其具有吡咯吡嘧啶骨架或其药用可接受盐，以及一种预防和/或治疗肿瘤的方法，结合烷基化剂和/或放射疗法。根据本发明的一方面，提供了以下一般公式（1）所代表的化合物或其药用可接受盐，以及一种结合烷基化剂和/或放射疗法预防和/或治疗肿瘤的方法。