4-{[4-(3,4-Dimethoxy-phenyl)-pyrimidin-2-ylamino]-methyl}-benzoic acid | 645401-62-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-{[4-(3,4-Dimethoxy-phenyl)-pyrimidin-2-ylamino]-methyl}-benzoic acid
• 英文别名: 4-({[4-(3,4-Dimethoxyphenyl)pyrimidin-2-yl]amino}methyl)benzoic acid；4-[[[4-(3,4-dimethoxyphenyl)pyrimidin-2-yl]amino]methyl]benzoic acid
• CAS: 645401-62-3
• 化学式: C₂₀H₁₉N₃O₄
• 分子量: 365.389
• InChiKey: OVWPGZOZZVKWNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  93.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-{[4-(3,4-Dimethoxy-phenyl)-pyrimidin-2-ylamino]-methyl}-benzoic acid 、 邻苯二胺 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(2-Amino-phenyl)-4-{[4-(3,4-dimethoxy-phenyl)-pyrimidin-2-ylamino]-methyl}-benzamide
  参考文献：
  名称：

  Design and synthesis of 4-[(s-triazin-2-ylamino)methyl]-N-(2-aminophenyl)-benzamides and their analogues as a novel class of histone deacetylase inhibitors

  摘要：

  Inhibition of histone deacetylases (HDAC) is emerging as a new strategy in human cancer therapy. The synthesis and biological evaluation of a variety of 4-(heteroaryl aminomethyl)-N-(2-aminophenyl)-benzamides is presented herein. From the different series bearing a six-membered heteroaromatic ring studied, the s-triazine series showed the best HDAC1 enzyme and in vitro anti-proliferative activities with IC50 values below micromolar range. Some of these compounds can also significantly reduce tumor growth in human tumor xenograft models in mice. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.009
• 作为产物：
  描述：

  在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 4-{[4-(3,4-Dimethoxy-phenyl)-pyrimidin-2-ylamino]-methyl}-benzoic acid
  参考文献：
  名称：

  Design and synthesis of 4-[(s-triazin-2-ylamino)methyl]-N-(2-aminophenyl)-benzamides and their analogues as a novel class of histone deacetylase inhibitors

  摘要：

  Inhibition of histone deacetylases (HDAC) is emerging as a new strategy in human cancer therapy. The synthesis and biological evaluation of a variety of 4-(heteroaryl aminomethyl)-N-(2-aminophenyl)-benzamides is presented herein. From the different series bearing a six-membered heteroaromatic ring studied, the s-triazine series showed the best HDAC1 enzyme and in vitro anti-proliferative activities with IC50 values below micromolar range. Some of these compounds can also significantly reduce tumor growth in human tumor xenograft models in mice. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.009

文献信息

• Methods for specifically inhibiting histone deacetylase-7 and 8
  申请人：——

  公开号：US20040072770A1

  公开（公告）日：2004-04-15

  This invention relates to the inhibition of histone deacetylase (HDAC) expression and enzymatic activity. The invention provides methods and reagents for inhibiting HDAC-7 and HDAC-8 by inhibiting expression at the nucleic acid level or inhibiting enzymatic activity at the protein level.

  本发明涉及抑制组蛋白去乙酰化酶（HDAC）表达和酶活性的方法。本发明提供了通过在核酸水平抑制表达或在蛋白质水平抑制酶活性来抑制HDAC-7和HDAC-8的方法和试剂。
• [EN] METHODS FOR SPECIFICALLY INHIBITING HISTONE DEACETYLASE-7 AND 8<br/>[FR] PROCEDE D'INHIBITION SPECIFIQUE DE L'HISTONE DEACETYLASE-7 ET 8
  申请人：METHYLGENE INC

  公开号：WO2004005513A2

  公开（公告）日：2004-01-15

  This invention relates to the inhibition of histone deacetylase (HDAC) expression and enzymatic activity. The invention provides methods and reagents for inhibiting HDAC-7 and HDAC-8 by inhibiting expression at the nucleic acid level or inhibiting enzymatic activity at the protein level.
• Design and synthesis of 4-[(s-triazin-2-ylamino)methyl]-N-(2-aminophenyl)-benzamides and their analogues as a novel class of histone deacetylase inhibitors
  作者：Isabelle Paquin、Stéphane Raeppel、Silvana Leit、Frédéric Gaudette、Nancy Zhou、Oscar Moradei、Oscar Saavedra、Naomy Bernstein、Franck Raeppel、Giliane Bouchain、Sylvie Fréchette、Soon H. Woo、Arkadii Vaisburg、Marielle Fournel、Ann Kalita、Marie-France Robert、Aihua Lu、Marie-Claude Trachy-Bourget、Pu Theresa Yan、Jianhong Liu、Jubrail Rahil、A. Robert MacLeod、Jeffrey M. Besterman、Zuomei Li、Daniel Delorme

  DOI：10.1016/j.bmcl.2007.12.009

  日期：2008.2

  Inhibition of histone deacetylases (HDAC) is emerging as a new strategy in human cancer therapy. The synthesis and biological evaluation of a variety of 4-(heteroaryl aminomethyl)-N-(2-aminophenyl)-benzamides is presented herein. From the different series bearing a six-membered heteroaromatic ring studied, the s-triazine series showed the best HDAC1 enzyme and in vitro anti-proliferative activities with IC50 values below micromolar range. Some of these compounds can also significantly reduce tumor growth in human tumor xenograft models in mice. (C) 2007 Elsevier Ltd. All rights reserved.