N-[4-{3-[(4-aminobutanoyl)amino]phenyl}-3-cyano-6-(2-hydroxyphenyl)pyridin-2-yl]thiophene-2-carboxamide hydrochloride | 1236299-05-0

• 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-[(4-aminobutanoyl)amino]phenyl}-3-cyano-6-(2-hydroxyphenyl)pyridin-2-yl]thiophene-2-carboxamide hydrochloride
• CAS: 1236299-05-0
• 化学式: C₂₇H₂₃N₅O₃S*ClH
• 分子量: 534.038
• InChiKey: HUOXYCKKGGYXDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  141.13
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  tert-butyl {4-[(3-{3-cyano-6-(2-hydroxyphenyl)-2-[(thiophen-2-ylcarbonyl)amino]pyridin-4-yl}phenyl)amino]-4-oxobutyl}carbamate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以41%的产率得到N-[4-{3-[(4-aminobutanoyl)amino]phenyl}-3-cyano-6-(2-hydroxyphenyl)pyridin-2-yl]thiophene-2-carboxamide hydrochloride
  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