3-[4-(N-Hydroxycarbamimidoyl)-3-methyl-phenyl]-propionic acid methyl ester | 905308-55-6

• 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: 3-[4-(N-Hydroxycarbamimidoyl)-3-methyl-phenyl]-propionic acid methyl ester
• CAS: 905308-55-6
• 化学式: C₁₂H₁₆N₂O₃
• 分子量: 236.271
• InChiKey: WNGNFEMJTLWFSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.91
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-[4-(N-Hydroxycarbamimidoyl)-3-methyl-phenyl]-propionic acid methyl ester 在 sodium hydroxide 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 14.0h， 生成 3-{4-[5-(4-Cyclohexyl-phenyl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-propionic acid
  参考文献：
  名称：

  Discovery of 3-arylpropionic acids as potent agonists of sphingosine-1-phosphate receptor-1 (S1P1) with high selectivity against all other known S1P receptor subtypes

  摘要：

  A series of 3-arylpropionic acids were synthesized as S1P(1) receptor agonists. Structure-activity relationship studies on the pendant phenyl ring revealed several structural features offering selectivity of S1P(1) binding against S1P(2-5). These highly selective SIP, agonists induced peripheral blood lymphocyte lowering in mice and one of them was found to be efficacious in a rat skin transplantation model, supporting that S1P(1) agonism is primarily responsible for the immunosuppressive efficacy observed in preclinical animal models. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.084
• 作为产物：
  描述：

  4-溴-2-甲基苯腈 在 palladium on activated charcoal bis(tri-tert-butylphosphine)palladium(0) 、 N-甲基二环己基胺 、 盐酸羟胺 、 氢气 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 20.0~70.0 ℃ 、103.42 kPa 条件下， 生成 3-[4-(N-Hydroxycarbamimidoyl)-3-methyl-phenyl]-propionic acid methyl ester
  参考文献：
  名称：

  Discovery of 3-arylpropionic acids as potent agonists of sphingosine-1-phosphate receptor-1 (S1P1) with high selectivity against all other known S1P receptor subtypes

  摘要：

  A series of 3-arylpropionic acids were synthesized as S1P(1) receptor agonists. Structure-activity relationship studies on the pendant phenyl ring revealed several structural features offering selectivity of S1P(1) binding against S1P(2-5). These highly selective SIP, agonists induced peripheral blood lymphocyte lowering in mice and one of them was found to be efficacious in a rat skin transplantation model, supporting that S1P(1) agonism is primarily responsible for the immunosuppressive efficacy observed in preclinical animal models. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.084