3-(naphthalen-2-yl)-N-(2-nitrophenyl)benzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(naphthalen-2-yl)-N-(2-nitrophenyl)benzamide
• 英文别名: 3-naphthalen-2-yl-N-(2-nitrophenyl)benzamide
• 化学式: C₂₃H₁₆N₂O₃
• 分子量: 368.392
• InChiKey: HHIFKRBLQVINTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(naphthalen-2-yl)-N-(2-nitrophenyl)benzamide 在 tin(II) chloride dihdyrate 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 以67%的产率得到N-(2-aminophenyl)-3-(naphthalen-2-yl)benzamide
  参考文献：
  名称：

  Design, synthesis and structure–activity relationship studies of novel sirtuin 2 (SIRT2) inhibitors with a benzamide skeleton

  摘要：

  Human sirtuin 2 (SIRT2) is an attractive target molecule for development of drugs to treat neurodegenerative diseases and cancer, because SIRT2 inhibitors have a protective effect against neurodegeneration and an anti-proliferative effect on cancer stem cells. We designed and synthesized a series of benzamide derivatives as SIRT2 inhibitor candidates. Among them, compound 17k showed the most potent SIRT2-inhibitory activity (IC50 = 0.60 mu M), with more than 150-fold selectivity over SIRT1 and SIRT3 isoforms (IC50 > 100 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.027
• 作为产物：
  描述：

  3-溴苯甲酸甲酯 在 四(三苯基膦)钯 、 草酰氯 、 lithium hydroxide monohydrate 、 水 、 sodium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 19.0h， 生成 3-(naphthalen-2-yl)-N-(2-nitrophenyl)benzamide
  参考文献：
  名称：

  Design, synthesis and structure–activity relationship studies of novel sirtuin 2 (SIRT2) inhibitors with a benzamide skeleton

  摘要：

  Human sirtuin 2 (SIRT2) is an attractive target molecule for development of drugs to treat neurodegenerative diseases and cancer, because SIRT2 inhibitors have a protective effect against neurodegeneration and an anti-proliferative effect on cancer stem cells. We designed and synthesized a series of benzamide derivatives as SIRT2 inhibitor candidates. Among them, compound 17k showed the most potent SIRT2-inhibitory activity (IC50 = 0.60 mu M), with more than 150-fold selectivity over SIRT1 and SIRT3 isoforms (IC50 > 100 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.027

文献信息

• Design, synthesis and structure–activity relationship studies of novel sirtuin 2 (SIRT2) inhibitors with a benzamide skeleton
  作者：Taki Sakai、Yotaro Matsumoto、Minoru Ishikawa、Kazuyuki Sugita、Yuichi Hashimoto、Nobuhiko Wakai、Akio Kitao、Era Morishita、Chikashi Toyoshima、Tomoatsu Hayashi、Tetsu Akiyama

  DOI：10.1016/j.bmc.2014.11.027

  日期：2015.1

  Human sirtuin 2 (SIRT2) is an attractive target molecule for development of drugs to treat neurodegenerative diseases and cancer, because SIRT2 inhibitors have a protective effect against neurodegeneration and an anti-proliferative effect on cancer stem cells. We designed and synthesized a series of benzamide derivatives as SIRT2 inhibitor candidates. Among them, compound 17k showed the most potent SIRT2-inhibitory activity (IC50 = 0.60 mu M), with more than 150-fold selectivity over SIRT1 and SIRT3 isoforms (IC50 > 100 mu M). (C) 2014 Elsevier Ltd. All rights reserved.