2-(1-Diethoxyphosphoryl-2-phenylethyl)-3-methyl-1-benzothiophene | 1372151-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-(1-Diethoxyphosphoryl-2-phenylethyl)-3-methyl-1-benzothiophene
• CAS: 1372151-82-0
• 化学式: C₂₁H₂₅O₃PS
• 分子量: 388.467
• InChiKey: VZXCBYCDPRUZAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲基苯并[B]噻吩-2-羰醛 在 sodium tetrahydroborate 、 正丁基锂 、 三溴化磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 38.0h， 生成 2-(1-Diethoxyphosphoryl-2-phenylethyl)-3-methyl-1-benzothiophene
  参考文献：
  名称：

  The design and synthesis of novel, phosphonate-containing transient receptor potential melastatin 8 (TRPM8) antagonists

  摘要：

  A series of benzothiophene-based phosphonates was synthesized and many analogs within the series were shown to be potent antagonists of the TRPM8 channel. The compounds were obtained as a racemic mixture in 5 synthetic steps, and were tested for TRPM8 antagonist activity in a recombinant, canine TRPM8-expressing cell line using a fluorometric imaging plate reader (FLIPR) assay. Structure-activity relationships were developed initially by modification of the core structure and subsequently by variation of the aromatic substituents and the phosphonate ester. Compound 9l was administered intraperitoneally to rats and demonstrated engagement of the TRPM8 target in both prevention and reversalmodes in an icilin-induced 'wet-dog' shake model. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.02.060

文献信息

• The design and synthesis of novel, phosphonate-containing transient receptor potential melastatin 8 (TRPM8) antagonists
  作者：Jay M. Matthews、Ning Qin、Raymond W. Colburn、Scott L. Dax、Mike Hawkins、James J. McNally、Laura Reany、Mark A. Youngman、Judith Baker、Tasha Hutchinson、Yi Liu、Mary Lou Lubin、Michael Neeper、Michael R. Brandt、Dennis J. Stone、Christopher M. Flores

  DOI：10.1016/j.bmcl.2012.02.060

  日期：2012.4

  A series of benzothiophene-based phosphonates was synthesized and many analogs within the series were shown to be potent antagonists of the TRPM8 channel. The compounds were obtained as a racemic mixture in 5 synthetic steps, and were tested for TRPM8 antagonist activity in a recombinant, canine TRPM8-expressing cell line using a fluorometric imaging plate reader (FLIPR) assay. Structure-activity relationships were developed initially by modification of the core structure and subsequently by variation of the aromatic substituents and the phosphonate ester. Compound 9l was administered intraperitoneally to rats and demonstrated engagement of the TRPM8 target in both prevention and reversalmodes in an icilin-induced 'wet-dog' shake model. (C) 2012 Published by Elsevier Ltd.