2-isopropoxy-5-[3-(2-methyl-4-vinyl-phenyl)-[1,2,4]oxadiazol-5-yl]-benzonitrile | 929202-27-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-isopropoxy-5-[3-(2-methyl-4-vinyl-phenyl)-[1,2,4]oxadiazol-5-yl]-benzonitrile
• CAS: 929202-27-7
• 化学式: C₂₁H₁₉N₃O₂
• 分子量: 345.401
• InChiKey: PZOZCZKGWOVUPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  71.94
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-isopropoxy-5-[3-(2-methyl-4-vinyl-phenyl)-[1,2,4]oxadiazol-5-yl]-benzonitrile 在 四氧化锇 sodium periodate 、 N-甲基吲哚酮 、 16-crown-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 methyl (2Z)-3-(4-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-3-methylphenyl)prop-2-enoate
  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
• 作为产物：
  描述：

  4-溴-2-甲基苯腈 在 bis(tributylphosphine) palladium 、 盐酸羟胺 、 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 cesium fluoride 作用下， 以 1,4-二氧六环 、 乙醇 、 乙腈 为溶剂， 反应 18.0h， 生成 2-isopropoxy-5-[3-(2-methyl-4-vinyl-phenyl)-[1,2,4]oxadiazol-5-yl]-benzonitrile
  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