2-[5-(prop-2-ynyloxy)heptyloxy]tetrahydro-2H-pyran | 832726-54-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-[5-(prop-2-ynyloxy)heptyloxy]tetrahydro-2H-pyran
• 英文别名: 2-({7-[(Prop-2-yn-1-yl)oxy]heptyl}oxy)oxane；2-(7-prop-2-ynoxyheptoxy)oxane
• CAS: 832726-54-2
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: TZMAJYSQYUYZLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  phenyl 4-(4-butoxyphenylsulfanyl)-2'-formylbiphenyl-3-sulfonate 、 2-[5-(prop-2-ynyloxy)heptyloxy]tetrahydro-2H-pyran 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.17h， 生成 phenyl 4-(4-butoxyphenylsulfanyl)-2'-[1-hydroxy-4-[7-(tetrahydro-2H-pyran-2-yloxy)heptyloxy]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-[(7-溴庚基)氧基]四氢-2H-吡喃 、 2-丙炔-1-醇 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-[5-(prop-2-ynyloxy)heptyloxy]tetrahydro-2H-pyran
  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

• Synthesis and SAR studies of a novel class of S1P1 receptor antagonists
  作者：Tsuyoshi Nakamura、Kiyoaki Yonesu、Yumiko Mizuno、Chie Suzuki、Yuki Sakata、Yoh Takuwa、Futoshi Nara、Susumu Satoh

  DOI：10.1016/j.bmc.2007.02.048

  日期：2007.5

  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.