tert-butyl {3-[(3-{6-[5-chloro-2-(methoxymethoxy)-phenyl]-3-cyano-2-[(thiophen-2-ylcarbonyl)amino]pyridin-4-yl}phenyl)amino]-3-oxopropyl}carbamate | 925922-16-3

• 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-[5-chloro-2-(methoxymethoxy)-phenyl]-3-cyano-2-[(thiophen-2-ylcarbonyl)amino]pyridin-4-yl}phenyl)amino]-3-oxopropyl}carbamate
• 英文别名: tert-butyl {3-[(3-{6-[5-chloro-2-(methoxymethoxy)phenyl]-3-cyano-2-[(2-thienylcarbonyl) amino]pyridin-4-yl}phenyl)amino]-3-oxopropyl}carbamate；tert-butyl N-[3-[3-[6-[5-chloro-2-(methoxymethoxy)phenyl]-3-cyano-2-(thiophene-2-carbonylamino)pyridin-4-yl]anilino]-3-oxopropyl]carbamate
• CAS: 925922-16-3
• 化学式: C₃₃H₃₂ClN₅O₆S
• 分子量: 662.166
• InChiKey: FRJFIYZLFULFRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  180
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl {3-[(3-{6-[5-chloro-2-(methoxymethoxy)-phenyl]-3-cyano-2-[(thiophen-2-ylcarbonyl)amino]pyridin-4-yl}phenyl)amino]-3-oxopropyl}carbamate 、 三氟乙酸 反应 1.5h， 以95%的产率得到N-{4-[3-(β-alanylamino)phenyl]-6-(5-chloro-2-hydroxyphenyl)-3-cyanopyridin-2-yl}thiophene-2-carboxamide trifluoroacetate
  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-{4-(3-aminophenyl)-6-[5-chloro-2-(methoxymethoxy)-phenyl]-3-cyanopyridin-2-yl}thiophene-2-carboxamide 、 Boc-beta-丙氨酸 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69%的产率得到tert-butyl {3-[(3-{6-[5-chloro-2-(methoxymethoxy)-phenyl]-3-cyano-2-[(thiophen-2-ylcarbonyl)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

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.