3-{4-[5-(4-isopropoxy-3-trifluoromethyl-phenyl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-butyric acid tert-butyl ester | 929202-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-{4-[5-(4-isopropoxy-3-trifluoromethyl-phenyl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-butyric acid tert-butyl ester
• CAS: 929202-16-4
• 化学式: C₂₇H₃₁F₃N₂O₄
• 分子量: 504.549
• InChiKey: MAXXLTHCIIHTPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.35
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  74.45
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-{4-[5-(4-isopropoxy-3-trifluoromethyl-phenyl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-butyric acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 3-(3-Methyl-4-{5-[4-(propan-2-yloxy)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}phenyl)butanoic 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
• 作为产物：
  描述：

  甲基丙烯酸叔丁酯 在 palladium on activated charcoal tris(dibenzylideneacetone)dipalladium (0) 、 N-甲基二环己基胺 、 盐酸羟胺 、 氢气 、 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 2-(二叔丁基膦)联苯 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 乙腈 为溶剂， 20.0~100.0 ℃ 、101.33 kPa 条件下， 反应 36.0h， 生成 3-{4-[5-(4-isopropoxy-3-trifluoromethyl-phenyl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-butyric acid tert-butyl ester
  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