2-amino-6-(2-methoxyphenyl)-4-(3-nitrophenyl)-pyridine-3-carbonitrile | 642040-15-1

• 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: 2-amino-6-(2-methoxyphenyl)-4-(3-nitrophenyl)-pyridine-3-carbonitrile
• 英文别名: 2-Amino-6-(2-methoxyphenyl)-4-(3-nitrophenyl)pyridine-3-carbonitrile
• CAS: 642040-15-1
• 化学式: C₁₉H₁₄N₄O₃
• 分子量: 346.345
• InChiKey: DSKAVBHSVWGYGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-6-(2-methoxyphenyl)-4-(3-nitrophenyl)-pyridine-3-carbonitrile 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Discovery of novel and selective IKK-β serine-threonine protein kinase inhibitors. Part 1

  摘要：

  IkappaB kinase beta (IKK-beta) is a serine-threonine protein kinase critically involved in the activation of the transcription factor Nuclear Factor kappa B (NF-kappaB) in response to various inflammatory stimuli. We have identified a small molecule inhibitor of IKK-beta. Optimization of the lead compound resulted in improvements in both in vitro and in vivo potency, and provided IKK-beta inhibitors exhibiting potent activity in an acute cytokine release model (LPS-induced TNFalpha). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01046-6
• 作为产物：
  描述：

  2'-甲氧基苯乙酮 、 间硝基苯甲醛 、 丙二腈 在 ammonium acetate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以10%的产率得到2-amino-6-(2-methoxyphenyl)-4-(3-nitrophenyl)-pyridine-3-carbonitrile
  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.
• Discovery of novel and selective IKK-β serine-threonine protein kinase inhibitors. Part 1
  作者：Toshiki Murata、Mitsuyuki Shimada、Sachiko Sakakibara、Takashi Yoshino、Hiroshi Kadono、Tsutomu Masuda、Makoto Shimazaki、Takuya Shintani、Kinji Fuchikami、Katsuya Sakai、Hisayo Inbe、Keisuke Takeshita、Toshiro Niki、Masaomi Umeda、Kevin B. Bacon、Karl B. Ziegelbauer、Timothy B. Lowinger

  DOI：10.1016/s0960-894x(02)01046-6

  日期：2003.3

  IkappaB kinase beta (IKK-beta) is a serine-threonine protein kinase critically involved in the activation of the transcription factor Nuclear Factor kappa B (NF-kappaB) in response to various inflammatory stimuli. We have identified a small molecule inhibitor of IKK-beta. Optimization of the lead compound resulted in improvements in both in vitro and in vivo potency, and provided IKK-beta inhibitors exhibiting potent activity in an acute cytokine release model (LPS-induced TNFalpha). (C) 2003 Elsevier Science Ltd. All rights reserved.