3-{3-cyano-6-(2-hydroxyphenyl)-2-[(thiophen-2-ylcarbonyl)amino]pyridin-4-yl}benzoic acid | 1236299-10-7

• 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: 3-{3-cyano-6-(2-hydroxyphenyl)-2-[(thiophen-2-ylcarbonyl)amino]pyridin-4-yl}benzoic acid
• 英文别名: 3-{3-Cyano-6-(2-hydroxyphenyl)-2-[(thiophen-2-ylcarbonyl)amino]pyridin-4-yl}benzoic acid；3-[3-cyano-6-(2-hydroxyphenyl)-2-(thiophene-2-carbonylamino)pyridin-4-yl]benzoic acid
• CAS: 1236299-10-7
• 化学式: C₂₄H₁₅N₃O₄S
• 分子量: 441.467
• InChiKey: RKYNKGUMMZZWOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  152
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-{3-cyano-6-[2-(methoxymethoxy)phenyl]-2-[(thiophen-2-ylcarbonyl)amino]pyridin-4-yl}benzoic acid 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以84%的产率得到3-{3-cyano-6-(2-hydroxyphenyl)-2-[(thiophen-2-ylcarbonyl)amino]pyridin-4-yl}benzoic acid
  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

• Synthesis and structure–activity relationships of 2-acylamino-4,6-diphenylpyridine derivatives as novel antagonists of GPR54
  作者：Toshitake Kobayashi、Satoshi Sasaki、Naoki Tomita、Seiji Fukui、Noritaka Kuroda、Masaharu Nakayama、Atsushi Kiba、Yoshihiro Takatsu、Tetsuya Ohtaki、Fumio Itoh

  DOI：10.1016/j.bmc.2010.04.036

  日期：2010.6.1

  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.