phenyl 4-(4-butoxyphenylsulfanyl)-2'-[1-hydroxy-4-(9-hydroxynonyloxy)but-2-ynyl]biphenyl-3-sulfonate | 832726-53-1

• 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: phenyl 4-(4-butoxyphenylsulfanyl)-2'-[1-hydroxy-4-(9-hydroxynonyloxy)but-2-ynyl]biphenyl-3-sulfonate
• 英文别名: Phenyl 2-(4-butoxyphenyl)sulfanyl-5-[2-[1-hydroxy-4-(9-hydroxynonoxy)but-2-ynyl]phenyl]benzenesulfonate
• CAS: 832726-53-1
• 化学式: C₄₁H₄₈O₇S₂
• 分子量: 716.96
• InChiKey: DGEJBLZDQQENQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  50
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 4-(4-butoxyphenylsulfanyl)-2'-[1-hydroxy-4-(9-hydroxynonyloxy)but-2-ynyl]biphenyl-3-sulfonate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以33%的产率得到Sodium;2-(4-butoxyphenyl)sulfanyl-5-[2-[1-hydroxy-4-(9-hydroxynonoxy)but-2-ynyl]phenyl]benzenesulfonate
  参考文献：
  名称：

  Synthesis and SAR studies of a novel class of S1P1 receptor antagonists

  摘要：

  A series of Sodium 4-[(4-butoxyphenyl)thio]-2'-substituted-1,1'-biphenyl-3-sulfonates were identified as functional sphingosine- 1-phosphate (S1P) antagonists with selectivity for the S1P(1) receptor subtype starting from chemical lead 2, which was found while screening our in-house compound library. We performed chemical modifications on each regional structure of compound 2, for example, on the three ring compartments, the benzyl substituents, and the long alkyl chain part. The introduction of a biphenyl skeletal structure and the installation of a hydroxyl group onto the terminal carbon in the side-chain region resulted in the potent derivative 35c, which showed > 500-fold more potent S1P(1) inhibitory activity than lead compound 2. We report herein the synthesis and structure-activity relationships of structurally novel S1P(1) receptor antagonists. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.048
• 作为产物：
  描述：

  2,5-二溴苯磺酰氯 在 四(三苯基膦)钯 正丁基锂 、 potassium carbonate 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.17h， 生成 phenyl 4-(4-butoxyphenylsulfanyl)-2'-[1-hydroxy-4-(9-hydroxynonyloxy)but-2-ynyl]biphenyl-3-sulfonate
  参考文献：
  名称：

  Synthesis and SAR studies of a novel class of S1P1 receptor antagonists

  摘要：

  A series of Sodium 4-[(4-butoxyphenyl)thio]-2'-substituted-1,1'-biphenyl-3-sulfonates were identified as functional sphingosine- 1-phosphate (S1P) antagonists with selectivity for the S1P(1) receptor subtype starting from chemical lead 2, which was found while screening our in-house compound library. We performed chemical modifications on each regional structure of compound 2, for example, on the three ring compartments, the benzyl substituents, and the long alkyl chain part. The introduction of a biphenyl skeletal structure and the installation of a hydroxyl group onto the terminal carbon in the side-chain region resulted in the potent derivative 35c, which showed > 500-fold more potent S1P(1) inhibitory activity than lead compound 2. We report herein the synthesis and structure-activity relationships of structurally novel S1P(1) receptor antagonists. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.048