phenyl 4-(4-butoxyphenylsulfanyl)-2'-formylbiphenyl-3-sulfonate | 832726-12-2

• 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'-formylbiphenyl-3-sulfonate
• 英文别名: phenyl4-(4-butoxyphenylthio)-2'-formyl-1,1'-biphenyl-3-sulfonate；Phenyl 2-(4-butoxyphenyl)sulfanyl-5-(2-formylphenyl)benzenesulfonate
• CAS: 832726-12-2
• 化学式: C₂₉H₂₆O₅S₂
• 分子量: 518.654
• InChiKey: UGGZJGYWPSPTMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 4-(4-butoxyphenylsulfanyl)-2'-formylbiphenyl-3-sulfonate 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 2.17h， 生成 phenyl 4-(4-butoxyphenylsulfanyl)-2'-[1-hydroxy-4-(11-hydroxyundecyloxy)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
• 作为产物：
  描述：

  2,5-二溴苯磺酰氯 在 四(三苯基膦)钯 potassium carbonate 、 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 乙二醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 phenyl 4-(4-butoxyphenylsulfanyl)-2'-formylbiphenyl-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

文献信息

• ＥＤＧ受容体拮抗作用を有するアルキレン誘導体
  申请人：三共株式会社

  公开号：JP2005120047A

  公开（公告）日：2005-05-12

  PROBLEM TO BE SOLVED: To provide novel compounds having EDG (endothelial differentiation gene) receptor antagonism which are useful as active components of drugs for preventing and/or treating inflammatory diseases or the like.

  SOLUTION: The compounds are represented by formula (I) (wherein R1is hydrogen or an alkyl group; R2is hydrogen present at any substitutable position on ring C or a substituent such as a hydroxy group, a carboxy group, and a nitro group; R3is hydrogen present at any substitutable position on ring D or a substitutent such as a hydroxy group and an aralkyloxy group; X is an alkylamino group, an amino group or the like; Y is a carboxy group, a sulfo group or a phosphono group; Z is oxygen, sulfur or the like; a ring represented by A is a 5- or 6-membered saturated or unsaturated hydrocarbon ring; and a ring represented by B is a 4- or 7-membered saturated or unsaturated hydrocarbon ring containing one -C=C- as a partial structure shown in the above formula) and include their salts and their esters.

  COPYRIGHT: (C)2005,JPO&NCIPI

  要解决的问题：提供具有EDG（内皮分化基因）受体拮抗作用的新化合物，这些化合物可作为预防和/或治疗炎症性疾病等药物的活性成分。 解决方案：这些化合物由式（I）表示（其中R1是氢或烷基；R2是存在于环C上的任何可取代位置的氢或取代基，如羟基、羧基和硝基；R3是存在于环D上的任何可取代位置的氢或取代基，如羟基和芳基氧基；X是烷基氨基团、氨基团或类似物；Y是羧基、磺酰基或膦酸基；Z是氧、硫或类似物；由A表示的环是5-或6-成员饱和或不饱和碳氢环；由B表示的环是含有一个-C=C-作为上述式中部分结构的4-或7-成员饱和或不饱和碳氢环），包括它们的盐和酯。 版权所有：（C）2005，JPO&NCIPI