(2R)-4-(6-aminopurin-9-yl)-2-hydroxybutyric acid methyl ester | 33303-39-8

• 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: (2R)-4-(6-aminopurin-9-yl)-2-hydroxybutyric acid methyl ester
• 英文别名: (R)-DZ2002；Wjb49MF6T3；methyl (2R)-4-(6-aminopurin-9-yl)-2-hydroxybutanoate
• CAS: 33303-39-8
• 化学式: C₁₀H₁₃N₅O₃
• 分子量: 251.245
• InChiKey: HNKGMGPCSSJYOT-ZCFIWIBFSA-N

物化性质

• 沸点：
  529.3±60.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 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：
  116
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  甲醇 、 (5R)-5-[2-(6-aminopurin-9-yl)ethyl]-2,2-dimethyl-5-oxo-[1,3]dioxolan-4-one 在 乙酰氯 作用下， 反应 3.5h， 生成 (2R)-4-(6-aminopurin-9-yl)-2-hydroxybutyric acid methyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of immunosuppressive agent DZ2002 and its stereoisomers

  摘要：

  DZ2002 and its related stereoisomers were efficiently synthesized. The optical data of (R)- and (S)-DZ2002 were disclosed here for the first time. Their inhibitory potency was evaluated on SAHase and MLR assay in the mean time. In accordance with respective inhibitory potency of SAHase, the immunosuppressive potency order was demonstrated as (S)-Z2002 > (Rac)-DZ2002 > (R)-DZ2002 > (Keto)DZ2002. These results indicate (S)-configuration of 2-chiral center in DZ2002 is important for binding with SAHase. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.017

文献信息

• Synthesis and biological evaluation of immunosuppressive agent DZ2002 and its stereoisomers
  作者：Yang-Ming Zhang、Yu Ding、Wei Tang、Wei Luo、Min Gu、Wei Lu、Jie Tang、Jian-Ping Zuo、Fa-Jun Nan

  DOI：10.1016/j.bmc.2008.09.017

  日期：2008.10

  DZ2002 and its related stereoisomers were efficiently synthesized. The optical data of (R)- and (S)-DZ2002 were disclosed here for the first time. Their inhibitory potency was evaluated on SAHase and MLR assay in the mean time. In accordance with respective inhibitory potency of SAHase, the immunosuppressive potency order was demonstrated as (S)-Z2002 > (Rac)-DZ2002 > (R)-DZ2002 > (Keto)DZ2002. These results indicate (S)-configuration of 2-chiral center in DZ2002 is important for binding with SAHase. (C) 2008 Elsevier Ltd. All rights reserved.