4-[1-[5-chloro-4-[N'-(2-methylphenyl)ureido]-2-methylphenylacetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]benzoic acid | 1093221-89-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[1-[5-chloro-4-[N'-(2-methylphenyl)ureido]-2-methylphenylacetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]benzoic acid
• 英文别名: 4-[[(2S,4S)-1-[2-[5-chloro-2-methyl-4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]-4-fluoropyrrolidin-2-yl]methoxy]benzoic acid
• CAS: 1093221-89-6
• 化学式: C₂₉H₂₉ClFN₃O₅
• 分子量: 554.018
• InChiKey: DOJRXKAOYCDVRA-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 4-[1-[5-chloro-4-[N'-(2-methylphenyl)ureido]-2-methylphenylacetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]benzoate 在 sodium hydroxide 、 水 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 生成 4-[1-[5-chloro-4-[N'-(2-methylphenyl)ureido]-2-methylphenylacetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]benzoic acid
  参考文献：
  名称：

  Identification of 4-[1-[3-chloro-4-[N’-(5-fluoro-2-methylphenyl)ureido]phenylacetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]benzoic acid as a potent, orally active VLA-4 antagonist

  摘要：

  Optimization of benzoic acid derivatives by introducing substituents into the diphenyl urea moiety led to the identification of compound 201 as a potent VLA-4 antagonist. Compound 201 inhibited eosinophil infiltration into bronchial alveolar lavage fluid in a murine asthma model by oral dosing and its efficacy was comparable to anti-mouse alpha 4 antibody (R1-2). Furthermore, this compound significantly blocked bronchial hyper-responsiveness in the model. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.020