tert-butyl (1S,2S)-2-[4-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]-3-methylphenyl]cyclopropane-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl (1S,2S)-2-[4-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]-3-methylphenyl]cyclopropane-1-carboxylate
• 化学式: C₂₇H₂₉N₃O₄
• 分子量: 459.545
• InChiKey: KNVJVODUOGOHEL-YADHBBJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S,2S)-2-[4-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]-3-methylphenyl]cyclopropane-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (1R,2R)-2-[4-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]-3-methylphenyl]cyclopropane-1-carboxylic acid
  参考文献：
  名称：

  SAR studies of 3-arylpropionic acids as potent and selective agonists of sphingosine-1-phosphate receptor-1 (S1P1) with enhanced pharmacokinetic properties

  摘要：

  Structure-activity relationship (SAR) studies of 3-arylpropionic acids-a class of novel S1P(1) selective agonists-by introducing substitution to the propionic acid chain and replacing the adjacent phenyl ring with pyridine led to a series of modified 3-arylpropionic acids with enhanced half-life in rat. These analogs (e.g., cyclopropanecarboxylic acids) exhibited longer half-life in rat than did unmodified 3-arylpropionic acids. This result suggests that metabolic oxidation at the propionic acid chain, particularly at the C3 benzylic position of 3-arylpropionic acids, is probably responsible for their short half-life in rodent. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.057