N-(toluene-4-sulfonyl)-L-prolyl-4-(4-(2-cyanophenyl)piperazin-1-yl)-L-phenylalanine tert-butyl ester | 618452-91-8

• 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: N-(toluene-4-sulfonyl)-L-prolyl-4-(4-(2-cyanophenyl)piperazin-1-yl)-L-phenylalanine tert-butyl ester
• 英文别名: tert-butyl (2S)-3-[4-[4-(2-cyanophenyl)piperazin-1-yl]phenyl]-2-[[(2S)-1-(4-methylphenyl)sulfonylpyrrolidine-2-carbonyl]amino]propanoate
• CAS: 618452-91-8
• 化学式: C₃₆H₄₃N₅O₅S
• 分子量: 657.834
• InChiKey: BWTKZXHHTRDDCQ-WEZIJMHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  47
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-(toluene-4-sulfonyl)-L-prolyl-4-(4-(2-cyanophenyl)piperazin-1-yl)-L-phenylalanine tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以71%的产率得到N-(toluene-4-sulfonyl)-L-prolyl-4-(4-(2-cyanophenyl)piperazin-1-yl)-L-phenylalanine
  参考文献：
  名称：

  Synthetic study of VLA-4/VCAM-1 inhibitors: Synthesis and structure–activity relationship of piperazinylphenylalanine derivatives

  摘要：

  To improve the poor pharmacokinetic characteristics of VLA-4 inhibitors, novel piperazinylphenylalanine derivatives were designed. This structure is expected to improve physicochemical properties by increasing overall basicity. By changing components at the 4-position of piperazine and the terminal group of the amido bond, 12t was found to be the most potent of this series of compounds. In addition, dichlorobenzoyl derivative 12aa exhibited better oral availability and showed efficacy in an in vivo model after oral administration. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.014
• 作为产物：
  描述：

  N-(toluene-4-sulfonyl)-L-prolyl-O-(trifluoromethanesulfonyl)-L-tyrosine tert-butyl ester 、 1-(2-苯甲腈)哌嗪 在 palladium diacetate caesium carbonate 、 2-(二叔丁基膦)联苯 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以35%的产率得到N-(toluene-4-sulfonyl)-L-prolyl-4-(4-(2-cyanophenyl)piperazin-1-yl)-L-phenylalanine tert-butyl ester
  参考文献：
  名称：

  Synthetic study of VLA-4/VCAM-1 inhibitors: Synthesis and structure–activity relationship of piperazinylphenylalanine derivatives

  摘要：

  To improve the poor pharmacokinetic characteristics of VLA-4 inhibitors, novel piperazinylphenylalanine derivatives were designed. This structure is expected to improve physicochemical properties by increasing overall basicity. By changing components at the 4-position of piperazine and the terminal group of the amido bond, 12t was found to be the most potent of this series of compounds. In addition, dichlorobenzoyl derivative 12aa exhibited better oral availability and showed efficacy in an in vivo model after oral administration. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.014