(+/-)-ethyl [4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-1-isoindolinylcarbonyl]-1-piperazinyl]acetate | 886447-56-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-ethyl [4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-1-isoindolinylcarbonyl]-1-piperazinyl]acetate
• CAS: 886447-56-9
• 化学式: C₃₄H₃₉N₅O₆
• 分子量: 613.714
• InChiKey: SHQQKTGSZAMQIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  45.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  120.52
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (+/-)-ethyl [4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-1-isoindolinylcarbonyl]-1-piperazinyl]acetate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 以48%的产率得到(+/-)-[4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-1-isoindolinylcarbonyl]-1-piperazinyl]acetic acid
  参考文献：
  名称：

  Synthesis, biological evaluation, and pharmacokinetic study of prolyl-1-piperazinylacetic acid and prolyl-4-piperidinylacetic acid derivatives as VLA-4 antagonists

  摘要：

  A series of prolyl-1-piperazinylacetic acid and prolyl-4-piperidinylacetic acid derivatives were synthesized and evaluated for their activity as VLA-4 antagonists. Of 22 compounds synthesized, 19 compounds showed potent activity with low nanomolar IC50 values. In addition, the representative compounds 11o and 11p with a hydroxy group in the pyrrolidine ring showed moderate plasma clearance in rats (11o, 30 ml/min/kg and 11p, 21 ml/min/kg) and in dogs (11o, 12ml/min/kg and 11p 9ml/min/kg). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.058
• 作为产物：
  描述：

  N-FMOC-异吲哚啉-1-羧酸 在 四丁基氟化铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 (+/-)-ethyl [4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-1-isoindolinylcarbonyl]-1-piperazinyl]acetate
  参考文献：
  名称：

  Synthesis, biological evaluation, and pharmacokinetic study of prolyl-1-piperazinylacetic acid and prolyl-4-piperidinylacetic acid derivatives as VLA-4 antagonists

  摘要：

  A series of prolyl-1-piperazinylacetic acid and prolyl-4-piperidinylacetic acid derivatives were synthesized and evaluated for their activity as VLA-4 antagonists. Of 22 compounds synthesized, 19 compounds showed potent activity with low nanomolar IC50 values. In addition, the representative compounds 11o and 11p with a hydroxy group in the pyrrolidine ring showed moderate plasma clearance in rats (11o, 30 ml/min/kg and 11p, 21 ml/min/kg) and in dogs (11o, 12ml/min/kg and 11p 9ml/min/kg). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.058