4-(5methoxy-1H-benzimidazol-2-yl-sulfanylmethyl)-benzoic acid | 398472-14-5

• 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-(5methoxy-1H-benzimidazol-2-yl-sulfanylmethyl)-benzoic acid
• 英文别名: 4-[(6-methoxy-1H-benzimidazol-2-yl)sulfanylmethyl]benzoic acid
• CAS: 398472-14-5
• 化学式: C₁₆H₁₄N₂O₃S
• 分子量: 314.365
• InChiKey: IEQJLSGPTIUFRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(5methoxy-1H-benzimidazol-2-yl-sulfanylmethyl)-benzoic acid 、 4-溴甲基苯甲酸甲酯 在 盐酸 、 glacial AcOH 、 sodium methylate 作用下， 以 乙酰丙酮 为溶剂， 以80%的产率得到4-(3-oxobutyl)benzoic acid
  参考文献：
  名称：

  Inhibitors of histone deacetylase

  摘要：

  本发明涉及组蛋白去乙酰化酶的抑制。本发明提供了用于抑制组蛋白去乙酰化酶酶活性的化合物和方法。本发明还提供了用于治疗细胞增殖性疾病和状况的药物组合物和方法。

  公开号：

  US06897220B2
• 作为产物：
  描述：

  Methyl-4-(5-methoxy-1H-benzimidazol-2-yl-sulfanylmethyl)-benzoate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 4-(5methoxy-1H-benzimidazol-2-yl-sulfanylmethyl)-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

• [EN] INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] INHIBITEURS DE L'HISTONE DEACETYLASE
  申请人：METHYLGENE INC

  公开号：WO2004069823A1

  公开（公告）日：2004-08-19

  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.

  该发明涉及抑制组蛋白去乙酰化酶的技术。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。该发明还提供了治疗细胞增殖性疾病和病症的组合物和方法。
• Inhibitors of Histone Deacetylase
  申请人：Delorme Daniel

  公开号：US20070213330A1

  公开（公告）日：2007-09-13

  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.

  本发明涉及抑制组蛋白去乙酰化酶的技术。本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。本发明还提供了治疗细胞增殖性疾病和病况的组合物和方法。
• Ligand-Based Design of a Potent and Selective Inhibitor of Cytochrome P450 2C19
  作者：Robert S. Foti、Dan A. Rock、Xiaogang Han、Robert A. Flowers、Larry C. Wienkers、Jan L. Wahlstrom

  DOI：10.1021/jm201346g

  日期：2012.2.9

  A series of omeprazole-based analogues was synthesized and assessed for inhibitory activity against CYP2C19. The data was used to build a CYP2C19 inhibition pharmacophore model for the series. The model was employed to design additional analogues with inhibitory potency against CYP2C19. Upon identifying inhibitors of CYP2C19, ligand-based design shifted to attenuating the rapid clearance observed for many of the inhibitors. While most analogues underwent metabolism on their aliphatic side chain, metabolite identification indicated that for analogues such as compound 30 which contain a heterocycle adjacent to the sulfur moiety, metabolism primarily occurred on the benzimidazole moiety. Compound 30 exhibited improved metabolic stability (Cl-int = 12.4 mL/min/nmol) and was selective in regard to inhibition of CYP2C19-catalyzed (S)-mephenytoin hydroxylation in human liver microsomes. Finally, representative compounds were docked into a homology model of CYP2C19 in an effort to understand the favorable inhibition or metabolism properties.
• INHIBITORS OF HISTONE DEACETYLASE
  申请人：Methylgene, Inc.

  公开号：EP1429765A2

  公开（公告）日：2004-06-23
• US6897220B2
  申请人：——

  公开号：US6897220B2

  公开（公告）日：2005-05-24