tert-butyl (3-{[3-(6-{2-[(tert-butoxycarbonyl)amino]-phenyl}-3-cyano-2-[(phenylcarbonyl)amino]pyridin-4-yl)-phenyl]amino}-3-oxopropyl)carbamate | 1236299-49-2

• 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: tert-butyl (3-{[3-(6-{2-[(tert-butoxycarbonyl)amino]-phenyl}-3-cyano-2-[(phenylcarbonyl)amino]pyridin-4-yl)-phenyl]amino}-3-oxopropyl)carbamate
• CAS: 1236299-49-2
• 化学式: C₃₈H₄₀N₆O₆
• 分子量: 676.772
• InChiKey: XEQRBMQTVSNWII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.74
• 重原子数：
  50.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  171.54
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (3-{[3-(6-{2-[(tert-butoxycarbonyl)amino]-phenyl}-3-cyano-2-[(phenylcarbonyl)amino]pyridin-4-yl)-phenyl]amino}-3-oxopropyl)carbamate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以78%的产率得到N-{4-[3-(β-alanylamino)phenyl]-6-(2-aminophenyl)-3-cyanopyridin-2-yl}benzamide dihydrochloride
  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：

  Boc-beta-丙氨酸 、 tert-butyl (2-{4-(3-aminophenyl)-5-cyano-6-[(phenyl-carbonyl)amino]pyridin-2-yl}phenyl)carbamate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以100%的产率得到tert-butyl (3-{[3-(6-{2-[(tert-butoxycarbonyl)amino]-phenyl}-3-cyano-2-[(phenylcarbonyl)amino]pyridin-4-yl)-phenyl]amino}-3-oxopropyl)carbamate
  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