2-(2-chloro-6-methylamino-purin-9-yl)-(2R,3R,4S)-tetrahydrothiophen-3,4-diol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2-(2-chloro-6-methylamino-purin-9-yl)-(2R,3R,4S)-tetrahydrothiophen-3,4-diol
• 英文别名: (2R,3R,4S)-2-(2-chloro-6-(methylamino)-9H-purin-9-yl)-tetrahydrothiophene-3,4-diol；(2R,3R,4S)-2-[2-chloro-6-(methylamino)purin-9-yl]thiolane-3,4-diol
• 化学式: C₁₀H₁₂ClN₅O₂S
• 分子量: 301.757
• InChiKey: ANLGHWMSNKUOET-NVMQTXNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,6-二氯嘌呤 在 盐酸 、 硫酸氢铵 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.5h， 生成 2-(2-chloro-6-methylamino-purin-9-yl)-(2R,3R,4S)-tetrahydrothiophen-3,4-diol
  参考文献：
  名称：

  Discovery of a New Nucleoside Template for Human A₃ Adenosine Receptor Ligands:  d-4‘-Thioadenosine Derivatives without 4‘-Hydroxymethyl Group as Highly Potent and Selective Antagonists

  摘要：

  Truncated D-4'-thioadenosine derivatives lacking the 4'-hydroxymethylene moiety were synthesized starting from D-mannose, using cyclization to the 4-thiosugar and one-step conversion of the diol to the acetate as key steps. At the human A(3) adenosine receptor (AR), N(6)-substituted purine analogues bound potently and selectively and acted as antagonists in a cyclic AMP functional assay. An N(6)-(3-chlorobenzyl)purine analogue 9b displayed a K(i) value of 1.66 nM at the human A(3) AR. Thus, truncated D-4'-thioadenosine is an excellent template for the design of novel A(3) AR antagonists to act at both human and murine species.

  DOI：

  10.1021/jm070259t

文献信息

• PHARMACEUTICAL COMPOSITION COMPRISING ADENOSINE DERIVATIVE FOR PREVENTION AND TREATMENT OF RETINAL DISEASE OR OPTIC NERVE DISEASE
  申请人：Future Medicine Co., Ltd.

  公开号：EP3725317A1

  公开（公告）日：2020-10-21

  The present invention relates to a pharmaceutical composition, an oral dosage form, and an eye drop, each of which comprise the compound represented by the Chemical Formula 1 or a pharmaceutically acceptable salt thereof as an effective ingredient for preventing and treating a retinal disease or an optic nerve disease. The pharmaceutical composition, the oral dosage form and the eye drop can effectively prevent or treat a retinal disease or an optic nerve disease.

  本发明涉及一种药物组合物、一种口服剂型和一种滴眼液，它们都包含化学式 1 所代表的化合物或其药学上可接受的盐，作为预防和治疗视网膜疾病或视神经疾病的有效成分。药物组合物、口服剂型和滴眼液可有效预防或治疗视网膜疾病或视神经疾病。
• WO2008/108508
  申请人：——

  公开号：——

  公开（公告）日：——
• US9018371B2
  申请人：——

  公开号：US9018371B2

  公开（公告）日：2015-04-28
• Discovery of a New Nucleoside Template for Human A₃ Adenosine Receptor Ligands:  <scp>d</scp>-4‘-Thioadenosine Derivatives without 4‘-Hydroxymethyl Group as Highly Potent and Selective Antagonists
  作者：Lak Shin Jeong、Seung Ah Choe、Prashantha Gunaga、Hea Ok Kim、Hyuk Woo Lee、Sang Kook Lee、Dilip K. Tosh、Amit Patel、Krishnan K. Palaniappan、Zhan-Guo Gao、Kenneth A. Jacobson、Hyung Ryong Moon

  DOI：10.1021/jm070259t

  日期：2007.7.1

  Truncated D-4'-thioadenosine derivatives lacking the 4'-hydroxymethylene moiety were synthesized starting from D-mannose, using cyclization to the 4-thiosugar and one-step conversion of the diol to the acetate as key steps. At the human A(3) adenosine receptor (AR), N(6)-substituted purine analogues bound potently and selectively and acted as antagonists in a cyclic AMP functional assay. An N(6)-(3-chlorobenzyl)purine analogue 9b displayed a K(i) value of 1.66 nM at the human A(3) AR. Thus, truncated D-4'-thioadenosine is an excellent template for the design of novel A(3) AR antagonists to act at both human and murine species.