3’-C-ethynyl-N9-β-D-ribofuranosyl-2-chloro-6-aminopurine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 3’-C-ethynyl-N9-β-D-ribofuranosyl-2-chloro-6-aminopurine
• 英文别名: (2R,3S,4R,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-3-ethynyl-2-(hydroxymethyl)tetrahydrofuran-3,4-diol；(2R,3S,4R,5R)-5-(6-amino-2-chloropurin-9-yl)-3-ethynyl-2-(hydroxymethyl)oxolane-3,4-diol
• 化学式: C₁₂H₁₂ClN₅O₄
• 分子量: 325.711
• InChiKey: QGWNYEYULPZJFE-OEBFKYMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  亚甲基双膦酰二氯 、 3’-C-ethynyl-N9-β-D-ribofuranosyl-2-chloro-6-aminopurine 在 磷酸三甲酯 、 三乙基碳酸氢铵缓冲液 作用下， 反应 5.25h， 生成 (((((2R,3S,4R,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-3-ethynyl-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)methyl)phosphonic acid
  参考文献：
  名称：

  WO2019246403A5

  摘要：

  公开号：

  WO2019246403A5
• 作为产物：
  描述：

  1,2,3,5-tetra-O-acetyl-3-C-ethynyl-D-ribo-pentofuranose 在 ammonium sulphate 、 氨 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 3’-C-ethynyl-N9-β-D-ribofuranosyl-2-chloro-6-aminopurine
  参考文献：
  名称：

  Exploring the purine core of 3′-C-ethynyladenosine (EAdo) in search of novel nucleoside therapeutics

  摘要：

  A series of new nucleoside analogues based on a C-3 branched ethynyl sugar derivative as present in 3'-C-ethynylcytidine (ECyd) and -adenosine (EAdo), combined with modified purine bases was synthetized and evaluated against a broad array of viruses and tumour cell lines. The pronounced cytostatic activity of EAdo was confirmed. EAdo and its 2,6-diaminopurine analogue showed inhibitory activity against vaccinia virus (EC50: 0.31 and 51 mu M, respectively). Derivative 10 on the other hand was found active against varicella zoster virus (EC50: 4.68 mu M). (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.03.005

文献信息

• [EN] ECTONUCLEOTIDASE INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS D'ÉCTONUCLÉOTIDASE ET LEURS MÉTHODES D'UTILISATION
  申请人：CALITHERA BIOSCIENCES INC

  公开号：WO2018119284A1

  公开（公告）日：2018-06-28

  The invention relates to novel heterocyclic compounds and pharmaceutical preparations thereof. The invention further relates to methods of treating or preventing cancer using the novel heterocyclic compounds of the invention.

  这项发明涉及新颖的杂环化合物及其制药制剂。该发明还涉及使用该发明的新颖杂环化合物治疗或预防癌症的方法。
• ECTONUCLEOTIDASE INHIBITORS AND METHODS OF USE THEREOF
  申请人：Chen Lijing

  公开号：US20180072742A1

  公开（公告）日：2018-03-15

  The invention relates to novel heterocyclic compounds and pharmaceutical preparations thereof. The invention further relates to methods of treating or preventing cancer using the novel heterocyclic compounds of the invention.

  该发明涉及新颖的杂环化合物及其药物制剂。该发明还涉及使用该新颖杂环化合物治疗或预防癌症的方法。
• Ectonucleotidase inhibitors and methods of use thereof
  申请人：Calithera Biosciences, Inc.

  公开号：US10472364B2

  公开（公告）日：2019-11-12

  The invention relates to novel heterocyclic compounds having CD73 inhibitory activity and pharmaceutical preparations thereof. The invention further relates to methods of treating or preventing cancer using the novel heterocyclic compounds of the invention.

  本发明涉及具有 CD73 抑制活性的新型杂环化合物及其药物制剂。本发明还涉及使用本发明的新型杂环化合物治疗或预防癌症的方法。
• Ectonucleotidase Inhibitors and Methods of Use Thereof
  申请人：Calithera Biosciences, Inc.

  公开号：US20180186827A1

  公开（公告）日：2018-07-05

  The invention relates to novel heterocyclic compounds and pharmaceutical preparations thereof. The invention further relates to methods of treating or preventing cancer using the novel heterocyclic compounds of the invention.
• [EN] ECTONUCLEOTIDASE INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS D'ÉCTONUCLÉOTIDASE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：CALITHERA BIOSCIENCES INC

  公开号：WO2018049145A1

  公开（公告）日：2018-03-15

  The invention relates to novel heterocyclic compounds and pharmaceutical preparations thereof. The invention further relates to methods of treating or preventing cancer using the novel heterocyclic compounds of the invention.