4-[(1H-benzimidazol-2-ylamino)methyl]benzoic acid | 110581-88-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-[(1H-benzimidazol-2-ylamino)methyl]benzoic acid
• CAS: 110581-88-9
• 化学式: C₁₅H₁₃N₃O₂
• 分子量: 267.287
• InChiKey: GCPHQBOYRDAMAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  78
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[(1H-benzimidazol-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 4-((1H-benzo[d]imidazol-2-ylamino)methyl)-N-(2-aminophenyl)benzamide
  参考文献：
  名称：

  4-(Heteroarylaminomethyl)-N-(2-aminophenyl)-benzamides and their analogs as a novel class of histone deacetylase inhibitors

  摘要：

  The synthesis and biological evaluation of a variety of 4-(heteroarylaminomethyl)-N-(2-aminophenyl)-benzamides and their analogs is described. Some of these compounds were shown to inhibit HDAC1 with IC50 values below the micromolar range, induce hyperacetylation of histones, upregulate expression of the tumor suppressor p21(WAF1/Cip1), and inhibit proliferation of human cancer cells. In addition, certain compounds of this class were active in several human tumor xenograft models in vivo. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.057
• 作为产物：
  描述：

  methyl 4-(1H-benzimidazol-2-yl-aminomethyl)benzoate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 4-[(1H-benzimidazol-2-ylamino)methyl]benzoic acid
  参考文献：
  名称：

  4-(Heteroarylaminomethyl)-N-(2-aminophenyl)-benzamides and their analogs as a novel class of histone deacetylase inhibitors

  摘要：

  The synthesis and biological evaluation of a variety of 4-(heteroarylaminomethyl)-N-(2-aminophenyl)-benzamides and their analogs is described. Some of these compounds were shown to inhibit HDAC1 with IC50 values below the micromolar range, induce hyperacetylation of histones, upregulate expression of the tumor suppressor p21(WAF1/Cip1), and inhibit proliferation of human cancer cells. In addition, certain compounds of this class were active in several human tumor xenograft models in vivo. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.057

文献信息

• 4-(Heteroarylaminomethyl)-N-(2-aminophenyl)-benzamides and their analogs as a novel class of histone deacetylase inhibitors
  作者：Sylvie Fréchette、Silvana Leit、Soon Hyung Woo、Guillaume Lapointe、Guillaume Jeannotte、Oscar Moradei、Isabelle Paquin、Giliane Bouchain、Stéphane Raeppel、Frédéric Gaudette、Nancy Zhou、Arkadii Vaisburg、Marielle Fournel、Pu Theresa Yan、Marie-Claude Trachy-Bourget、Ann Kalita、Marie-France Robert、Aihua Lu、Jubrail Rahil、A. Robert MacLeod、Jeffrey M. Besterman、Zuomei Li、Daniel Delorme

  DOI：10.1016/j.bmcl.2007.12.057

  日期：2008.2

  The synthesis and biological evaluation of a variety of 4-(heteroarylaminomethyl)-N-(2-aminophenyl)-benzamides and their analogs is described. Some of these compounds were shown to inhibit HDAC1 with IC50 values below the micromolar range, induce hyperacetylation of histones, upregulate expression of the tumor suppressor p21(WAF1/Cip1), and inhibit proliferation of human cancer cells. In addition, certain compounds of this class were active in several human tumor xenograft models in vivo. (c) 2008 Elsevier Ltd. All rights reserved.