methyl (2S)-3-(4-aminophenyl)-2-[(2,6-dimethylbenzoyl)amino]propanoate | 220847-35-8

• 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: methyl (2S)-3-(4-aminophenyl)-2-[(2,6-dimethylbenzoyl)amino]propanoate
• CAS: 220847-35-8
• 化学式: C₁₉H₂₂N₂O₃
• 分子量: 326.395
• InChiKey: QXMAOPPITPVKAN-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S)-3-(4-aminophenyl)-2-[(2,6-dimethylbenzoyl)amino]propanoate 在 sodium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 生成 (S)-3-[4-(2,6-Dichloro-benzoylamino)-phenyl]-2-(2,6-dimethyl-benzoylamino)-propionic acid
  参考文献：
  名称：

  Focused library approach for identification of new N-acylphenylalanines as VCAM/VLA-4 antagonists

  摘要：

  A structure-based focused library approach was employed in an effort to identify more lipophilic replacements for the N-benzylpyroglutamyl group of the VCAM/VLA-4 antagonist 2. This effort led to the discovery of two new classes of potent antagonists characterized by the N-(alpha-phenylcyclopentanoyl- and the N-(2,6-dimethylbenzoyl)-derivatives 60 and 64. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00201-9
• 作为产物：
  描述：

  4-硝基-L-苯丙氨酸 在 盐酸 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 tin(ll) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (2S)-3-(4-aminophenyl)-2-[(2,6-dimethylbenzoyl)amino]propanoate
  参考文献：
  名称：

  Focused library approach for identification of new N-acylphenylalanines as VCAM/VLA-4 antagonists

  摘要：

  A structure-based focused library approach was employed in an effort to identify more lipophilic replacements for the N-benzylpyroglutamyl group of the VCAM/VLA-4 antagonist 2. This effort led to the discovery of two new classes of potent antagonists characterized by the N-(alpha-phenylcyclopentanoyl- and the N-(2,6-dimethylbenzoyl)-derivatives 60 and 64. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00201-9

文献信息

• N-Alkanoylphenylalanine derivatives
  申请人：F.HOFFMANN-LA ROCHE AG

  公开号：EP1403247A1

  公开（公告）日：2004-03-31

  Compounds of the formula: as well as their salts and esters are disclosed wherein X, X', Z, and Y are as described in the specification and which have activity as inhibitors of binding between VCAM-1 and cells expressing VLA-4. Such compounds are useful for treating diseases whose symptoms and/or damage are related to the binding of VCAM-1 to cells expressing VLA-4.

  本发明公开了式 及其盐类和酯类，其中 X、X'、Z 和 Y 如说明书所述，具有抑制 VCAM-1 与表达 VLA-4 的细胞之间结合的活性。此类化合物可用于治疗其症状和/或损伤与 VCAM-1 与表达 VLA-4 的细胞结合有关的疾病。
• N-ALKANOYLPHENYLALANINE DERIVATIVES
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1005445A1

  公开（公告）日：2000-06-07
• US6197794B1
  申请人：——

  公开号：US6197794B1

  公开（公告）日：2001-03-06
• US6229011B1
  申请人：——

  公开号：US6229011B1

  公开（公告）日：2001-05-08
• [EN] N-ALKANOYLPHENYLALANINE DERIVATIVES<br/>[FR] DERIVES DE N-ALCANOYLPHENILALANINE
  申请人：——

  公开号：WO1999010312A1

  公开（公告）日：1999-03-04

  [EN] Compounds of formula (1) as well as their salts and esters are disclosed wherein X, X', Z and Y are as described in the specification and which have activity as inhibitors of binding between VCAM-1 and cells expressing VLA-4. Such compounds are useful for treating diseases whose symptoms and/or damage are related to the binding of VCAM-1 to cells expressing VLA-4.
  [FR] La présente invention concerne des composés représentés par la formule générale (1), ainsi que leurs sels et esters. En l'occurrence, X, X', Z et Y, qui sont conformes aux descriptions des spécifications de la présente demande, présentent une activité d'inhibition de la liaison entre le VCAM-1 et les cellules à expression de VLA-4. De tels composés conviennent pour le traitement d'affections dont les symptômes et/ou les atteintes sont en relation avec la liaison entre VCAM-1 et les cellules à expression de VLA-4.