N-[4-(3-aminophenyl)-6-(2-{[tert-butyl(dimethyl)silyl]-oxy}phenyl)-3-cyanopyridin-2-yl]thiophene-2-carboxamide | 925921-62-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-[4-(3-aminophenyl)-6-(2-{[tert-butyl(dimethyl)silyl]-oxy}phenyl)-3-cyanopyridin-2-yl]thiophene-2-carboxamide
• 英文别名: N-[4-(3-aminophenyl)-6-[2-[tert-butyl(dimethyl)silyl]oxyphenyl]-3-cyanopyridin-2-yl]thiophene-2-carboxamide
• CAS: 925921-62-6
• 化学式: C₂₉H₃₀N₄O₂SSi
• 分子量: 526.734
• InChiKey: XUZKTRICTFEWHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.57
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[4-(3-aminophenyl)-6-(2-{[tert-butyl(dimethyl)silyl]-oxy}phenyl)-3-cyanopyridin-2-yl]thiophene-2-carboxamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以17%的产率得到N-[4-(3-aminophenyl)-3-cyano-6-(2-hydroxyphenyl)-pyridin-2-yl]thiophene-2-carboxamide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 2-acylamino-4,6-diphenylpyridine derivatives as novel antagonists of GPR54

  摘要：

  GPR54 is a G protein-coupled receptor (GPCR) which was formerly an orphan receptor. Recent functional study of GPR54 revealed that the receptor has an essential role to modulate sex-hormones including GnRH. Though antagonists of GPR54 are expected to be novel drugs for sex-hormone dependent diseases such as prostate cancer or endometriosis, small molecule GPR54 antagonists have not been reported. We have synthesized a series of 2-acylamino-4,6-diphenylpyridines to identify potent GPR54 antagonists. Detailed structure-activity relationship studies led to compound 9l with an IC50 value of 3.7 nM in a GPR54 binding assay, and apparent antagonistic activity in a cellular functional assay. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.036
• 作为产物：
  描述：

  N-[6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-cyano-4-(3-nitrophenyl)pyridin-2-yl]thiophene-2-carboxamide 在 水 、 铁粉 、 氯化铵 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以95%的产率得到N-[4-(3-aminophenyl)-6-(2-{[tert-butyl(dimethyl)silyl]-oxy}phenyl)-3-cyanopyridin-2-yl]thiophene-2-carboxamide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 2-acylamino-4,6-diphenylpyridine derivatives as novel antagonists of GPR54

  摘要：

  GPR54 is a G protein-coupled receptor (GPCR) which was formerly an orphan receptor. Recent functional study of GPR54 revealed that the receptor has an essential role to modulate sex-hormones including GnRH. Though antagonists of GPR54 are expected to be novel drugs for sex-hormone dependent diseases such as prostate cancer or endometriosis, small molecule GPR54 antagonists have not been reported. We have synthesized a series of 2-acylamino-4,6-diphenylpyridines to identify potent GPR54 antagonists. Detailed structure-activity relationship studies led to compound 9l with an IC50 value of 3.7 nM in a GPR54 binding assay, and apparent antagonistic activity in a cellular functional assay. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.036

文献信息

• EP1921066
  申请人：——

  公开号：——

  公开（公告）日：——