4-(1-Methyl-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl)-benzoic Acid | 503039-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-(1-Methyl-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl)-benzoic Acid
• 英文别名: 4-[(1-Methyl-2,4-dioxoquinazolin-3-yl)methyl]benzoic acid
• CAS: 503039-60-9
• 化学式: C₁₇H₁₄N₂O₄
• 分子量: 310.309
• InChiKey: PESQDBIERGWUGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  77.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(1-Methyl-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl)-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-(1-methyl-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl)-benzamide
  参考文献：
  名称：

  N-(2-Amino-phenyl)-4-(heteroarylmethyl)-benzamides as new histone deacetylase inhibitors

  摘要：

  A variety of N-(2-amino-phenyl)-4-(heteroarylmethyl)-benzamides were designed and synthesized. These compounds were shown to inhibit recombinant human HDAC I with IC50 values in the sub-micromolar range. In human cancer cells growing in culture these compounds induced hyperacetylation of histones, induced the expression of the tumor suppressor protein p21(WAF1/Cip1), and inhibited cellular proliferation. Certain compounds of this class also showed in vivo activity in various human tumor xenograft models in mice. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.050
• 作为产物：
  描述：

  4-((2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl)methyl)benzoic acid 、 碘甲烷 在 potassium carbonate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 四氢呋喃 为溶剂， 生成 4-(1-Methyl-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl)-benzoic Acid
  参考文献：
  名称：

  N-(2-Amino-phenyl)-4-(heteroarylmethyl)-benzamides as new histone deacetylase inhibitors

  摘要：

  A variety of N-(2-amino-phenyl)-4-(heteroarylmethyl)-benzamides were designed and synthesized. These compounds were shown to inhibit recombinant human HDAC I with IC50 values in the sub-micromolar range. In human cancer cells growing in culture these compounds induced hyperacetylation of histones, induced the expression of the tumor suppressor protein p21(WAF1/Cip1), and inhibited cellular proliferation. Certain compounds of this class also showed in vivo activity in various human tumor xenograft models in mice. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.050

文献信息

• Inhibitors of histone deacetylase
  申请人：MethylGene, Inc.

  公开号：US20040142953A1

  公开（公告）日：2004-07-22

  The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

  这项发明涉及抑制组蛋白去乙酰化酶。该发明提供了抑制组蛋白去乙酰化酶酶活性的化合物和方法。该发明还提供了用于治疗细胞增殖性疾病和病况的组合物和方法。
• US6897220B2
  申请人：——

  公开号：US6897220B2

  公开（公告）日：2005-05-24
• US7595343B2
  申请人：——

  公开号：US7595343B2

  公开（公告）日：2009-09-29
• US7838520B2
  申请人：——

  公开号：US7838520B2

  公开（公告）日：2010-11-23
• N-(2-Amino-phenyl)-4-(heteroarylmethyl)-benzamides as new histone deacetylase inhibitors
  作者：Arkadii Vaisburg、Isabelle Paquin、Naomy Bernstein、Sylvie Frechette、Frederic Gaudette、Silvana Leit、Oscar Moradei、Stephane Raeppel、Nancy Zhou、Giliane Bouchain、Soon Hyung Woo、Zhiyun Jin、Jeff Gillespie、James Wang、Marielle Fournel、Pu Theresa Yan、Marie-Claude Trachy-Bourget、Marie-France Robert、Aihua Lu、Jimmy Yuk、Jubrail Rahil、A. Robert MacLeod、Jeffrey M. Besterman、Zuomei Li、Daniel Delorme

  DOI：10.1016/j.bmcl.2007.10.050

  日期：2007.12

  A variety of N-(2-amino-phenyl)-4-(heteroarylmethyl)-benzamides were designed and synthesized. These compounds were shown to inhibit recombinant human HDAC I with IC50 values in the sub-micromolar range. In human cancer cells growing in culture these compounds induced hyperacetylation of histones, induced the expression of the tumor suppressor protein p21(WAF1/Cip1), and inhibited cellular proliferation. Certain compounds of this class also showed in vivo activity in various human tumor xenograft models in mice. (c) 2007 Elsevier Ltd. All rights reserved.