ethyl 3-(2-amino-6-chloro-9H-purin-9-yl)propionate | 933477-60-2

• 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: ethyl 3-(2-amino-6-chloro-9H-purin-9-yl)propionate
• 英文别名: 3-(2-amino-6-chloro-9H-purine-9-yl)propionic acid ethyl ester；Ethyl 3-(2-amino-6-chloropurin-9-yl)propanoate
• CAS: 933477-60-2
• 化学式: C₁₀H₁₂ClN₅O₂
• 分子量: 269.691
• InChiKey: TUNHSZPYPWWKHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  95.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 3-(2-amino-6-chloro-9H-purin-9-yl)propionate 、 t-butyl piperidin-3-ylcarbamate 在 N,N-二异丙基乙胺 作用下， 以 异丙醇 为溶剂， 反应 20.0h， 以90%的产率得到C₂₀H₃₁N₇O₄
  参考文献：
  名称：

  Pleuromutilin derivatives having a purine ring. Part 1: New compounds with promising antibacterial activity against resistant Gram-positive pathogens

  摘要：

  In the course of our research aimed at the discovery of metabolic stable pleuromutilin derivatives with more potent antibacterial activity against Gram-positive pathogens than previous analogues, a series of compounds bearing a purine ring were prepared and evaluated. From SAR studies, we identified two promising compounds 85 and 87, which have excellent in vitro activity against a number of Gram-positive pathogens, including existing drug-resistant strains, and potent in vivo efficacy. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.011
• 作为产物：
  描述：

  2-氨基-6-氯嘌呤 、 丙烯酸乙酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以65%的产率得到ethyl 3-(2-amino-6-chloro-9H-purin-9-yl)propionate
  参考文献：
  名称：

  Pleuromutilin derivatives having a purine ring. Part 1: New compounds with promising antibacterial activity against resistant Gram-positive pathogens

  摘要：

  In the course of our research aimed at the discovery of metabolic stable pleuromutilin derivatives with more potent antibacterial activity against Gram-positive pathogens than previous analogues, a series of compounds bearing a purine ring were prepared and evaluated. From SAR studies, we identified two promising compounds 85 and 87, which have excellent in vitro activity against a number of Gram-positive pathogens, including existing drug-resistant strains, and potent in vivo efficacy. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.011

文献信息

• WO2007/37518
  申请人：——

  公开号：——

  公开（公告）日：——
• Water-Soluble Pleuromutilin Derivative with Excellent in Vitro and in Vivo Antibacterial Activity against Gram-Positive Pathogens
  作者：Yoshimi Hirokawa、Hironori Kinoshita、Tomoyuki Tanaka、Katsuhisa Nakata、Noriyuki Kitadai、Koichi Fujimoto、Shigeki Kashimoto、Tsuyoshi Kojima、Shiro Kato

  DOI：10.1021/jm8000136

  日期：2008.4.1

  Although earlier pleuromutilin analogues showed potent in vitro antibacterial activity against some Gram-positive pathogens, their in vivo efficacy was low because of insufficient pharmacokinetic properties. We designed novel thioether pleuromutilin derivatives having a purine ring as a polar and water solubilizing group and identified a promising pleuromutilin analogue 6 with good Solubility in water (similar to 50 mg/mL). Compound 6 exhibited excellent in vitro and in vivo antibacterial activity against some Gram-positive strains, including drug-resistant pathogens.
• Pleuromutilin derivatives having a purine ring. Part 1: New compounds with promising antibacterial activity against resistant Gram-positive pathogens
  作者：Yoshimi Hirokawa、Hironori Kinoshita、Tomoyuki Tanaka、Takanori Nakamura、Koichi Fujimoto、Shigeki Kashimoto、Tsuyoshi Kojima、Shiro Kato

  DOI：10.1016/j.bmcl.2008.05.011

  日期：2008.6

  In the course of our research aimed at the discovery of metabolic stable pleuromutilin derivatives with more potent antibacterial activity against Gram-positive pathogens than previous analogues, a series of compounds bearing a purine ring were prepared and evaluated. From SAR studies, we identified two promising compounds 85 and 87, which have excellent in vitro activity against a number of Gram-positive pathogens, including existing drug-resistant strains, and potent in vivo efficacy. (C) 2008 Elsevier Ltd. All rights reserved.