tert-butyl 3-[5-(N'-hydroxycarbamimidoyl)-6-methylpyridin-2-yl]propanoate | 856165-75-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl 3-[5-(N'-hydroxycarbamimidoyl)-6-methylpyridin-2-yl]propanoate
• CAS: 856165-75-8
• 化学式: C₁₄H₂₁N₃O₃
• 分子量: 279.339
• InChiKey: OKQXJVBBZWNLSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-[5-(N'-hydroxycarbamimidoyl)-6-methylpyridin-2-yl]propanoate 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 18.0h， 生成 3-(5-(5-(3-cyano-4-isopropyloxyphenyl)-1,2,4-oxadiazol-3-yl)-6-methylpyridin-2-yl)propanoic 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：

  2-甲基-3-羟基-6-碘吡啶 在 palladium on activated charcoal palladium diacetate 、 四(三苯基膦)钯 、 盐酸羟胺 、 四丁基氯化铵 、 氢气 、 碳酸氢钠 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 20.0~85.0 ℃ 、101.33 kPa 条件下， 生成 tert-butyl 3-[5-(N'-hydroxycarbamimidoyl)-6-methylpyridin-2-yl]propanoate
  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