4-[[(2,6-Dichlorophenyl)carbonyl]amino]-N-[[2,6-bis-(1-methylethyl)phenyl]carbonyl]-L-phenylalanine methyl ester | 220848-19-1

• 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-[[2,6-bis-(1-methylethyl)phenyl]carbonyl]-L-phenylalanine methyl ester
• 英文别名: methyl (2S)-3-[4-[(2,6-dichlorobenzoyl)amino]phenyl]-2-[[2,6-di(propan-2-yl)benzoyl]amino]propanoate
• CAS: 220848-19-1
• 化学式: C₃₀H₃₂Cl₂N₂O₄
• 分子量: 555.501
• InChiKey: XKYCEBZXANPPAU-VWLOTQADSA-N

物化性质

• 沸点：
  624.3±55.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[[(2,6-Dichlorophenyl)carbonyl]amino]-N-[[2,6-bis-(1-methylethyl)phenyl]carbonyl]-L-phenylalanine methyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (S)-3-[4-(2,6-Dichloro-benzoylamino)-phenyl]-2-(2,6-diisopropyl-benzoylamino)-propionic acid
  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
• 作为产物：
  描述：

  2,6-二氯苯甲酰氯 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 4-[[(2,6-Dichlorophenyl)carbonyl]amino]-N-[[2,6-bis-(1-methylethyl)phenyl]carbonyl]-L-phenylalanine methyl ester
  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.

  公式为的化合物已经被披露，具有作为VCAM-1和表达VLA-4的细胞之间结合抑制剂的活性。这样的化合物对于治疗症状和/或损伤与VCAM-1与表达VLA-4的细胞之间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：EP1005445B1

  公开（公告）日：2004-05-26
• US6229011B1
  申请人：——

  公开号：US6229011B1

  公开（公告）日：2001-05-08
• N-Aroyl-l-Phenylalanine Derivatives as VCAM/VLA-4 Antagonists
  作者：Achyutharao Sidduri、Jefferson W. Tilley、Jian Ping Lou、Li Chen、Gerry Kaplan、Frank Mennona、Robert Campbell、Robert Guthrie、Tai-Nan Huang、Karen Rowan、Virginia Schwinge、Louis M. Renzetti

  DOI：10.1016/s0960-894x(02)00387-6

  日期：2002.9

  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.