4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]sulfonyl]phenyl]carbonyl]-L-phenylalanine

• 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: 4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]sulfonyl]phenyl]carbonyl]-L-phenylalanine
• 英文别名: (2S)-2-[[2-chloro-4-[(3-hydroxyphenyl)methylsulfamoyl]benzoyl]amino]-3-[4-[(2,6-dichlorobenzoyl)amino]phenyl]propanoic acid
• 化学式: C₃₀H₂₄Cl₃N₃O₇S
• 分子量: 676.961
• InChiKey: IOGXXTUITAJELB-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  170
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,6-二氯苯甲酰氯 在 盐酸 、 sodium hydroxide 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]sulfonyl]phenyl]carbonyl]-L-phenylalanine
  参考文献：
  名称：

  N-Aroyl-l-Phenylalanine Derivatives as VCAM/VLA-4 Antagonists

  摘要：

  A series of N-benzoyl-4-[(2,6-dichlorobenzoyl)amino]-L-phenylalanine derivatives was prepared in order to optimize the substitution on the N-benzoyl moiety for VCAM/VLA-4 antagonist activity. Disubstitution in the 2- and 6-positions is favored and a range of small alkyl and halogen are tolerated. A model of the bioactive conformation of these compounds is proposed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00387-6

文献信息

• N-aroylphenylalanine derivative VCAM-1 inhibitors
  申请人：Hoffman-La Roche Inc.

  公开号：US06229011B1

  公开（公告）日：2001-05-08

  Compounds of the formula: are disclosed 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.

  揭示了具有以下化学式的化合物，这些化合物具有作为VCAM-1和表达VLA-4的细胞之间结合抑制剂的活性。这些化合物对于治疗症状和/或损害与VCAM-1与表达VLA-4的细胞结合有关的疾病是有用的。
• 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
• 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.