4-<(2'-thiobenzimidazol)methyl>benzoic acid | 194479-08-8

• 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-<(2'-thiobenzimidazol)methyl>benzoic acid
• 英文别名: 4-((1H-benzo[d]imidazol-2-ylthio)methyl)benzoic acid；4-(2-benzimidazolethiomethyl)benzoic acid；BI-87D4；Hbitmb；2-(4-Carboxybenzylthio)benzimidazole；4-[(1H-1,3-benzodiazol-2-ylsulfanyl)methyl]benzoic acid；4-(1H-benzimidazol-2-ylsulfanylmethyl)benzoic acid
• CAS: 194479-08-8
• 化学式: C₁₅H₁₂N₂O₂S
• mdl: MFCD05263787
• 分子量: 284.338
• InChiKey: HSDSEYKDYSEFBN-UHFFFAOYSA-N

物化性质

• 沸点：
  562.2±60.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)
• 溶解度：
  39.2 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  91.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙醇 、 4-<(2'-thiobenzimidazol)methyl>benzoic acid 在 硫酸 作用下， 生成 ethyl 4-<(2'-thiobenzimidazol)methyl>benzoate
  参考文献：
  名称：

  Benzimidazol-2-yl or benzimidazol-2-ylthiomethyl benzoylguanidines as novel Na+/H+ exchanger inhibitors, synthesis and protection against ischemic-reperfusion injury

  摘要：

  A novel series of benzimidazol-2-yl or benzimidazol-2-ylthiomethyl benzoylguanidines were designed and synthesized as Na+/H(+)exchanger inhibitors. Most of them were found to inhibit NHE1-mediated platelet swelling in a concentration-dependent manner, and to have significant cardioprotective effect against myocardial ischemic-reperfusion injury, among which compounds 10a and 34 were more potent than cariporide in both in vivo and in vitro tests. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.035
• 作为产物：
  描述：

  methyl 4-(((1H-benzo[d]imidazol-2-yl)thio)methyl)benzoate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 4-<(2'-thiobenzimidazol)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

• BENZIMIDAZOLE DERIVATIVES AS MITOCHONDRIAL FUNCTION MODULATORS
  申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY

  公开号：US20140114067A1

  公开（公告）日：2014-04-24

  Provided are a benzimidazole derivative modulating mitochondrial functions and having pharmaceutical activity as a neuro-protective agent, and a pharmaceutical composition including the compound as an active ingredient.

  提供了一种调节线粒体功能并具有药用活性作为神经保护剂的苯并咪唑衍生物，以及包含该化合物作为活性成分的药物组合物。
• 1,3-thiazoles and their use as immunomodulators
  申请人：Hoechst Aktiengesellschaft

  公开号：US04762848A1

  公开（公告）日：1988-08-09

  Heterocyclic sulfides of the general formula heterocycle-S-R, a process for their preparation and, in particular, their use for immunostimulation, immunorestoration and cytostatic treatment, and pharmaceutical agents, which contain a sulfide of this type, for these indications.

  本发明涉及一般式为杂环-S-R的杂环硫化物的制备方法，特别是它们用于免疫刺激、免疫恢复和细胞毒素治疗的用途，以及含有此类硫化物的药物制剂，用于上述适应症。
• Heterocyclische Sulfide, Verfahren zu ihrer Herstellung und pharmazeutische Mittel, die diese Verbindungen enthalten
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0194572A1

  公开（公告）日：1986-09-17

  Heterocyclische Sulfide der allgemeinen Formel Heterocyclus-S-R, Verfahren zu ihrer Herstellung und insbesondere ihre Verwendung zur Immunstimulation, Immunrestauration und zytostatischen Behandlung, sowie pharmazeutische Mittel für diese Indikationen, die ein solches Sulfid enthalten.

  通式为 Heterocyclus-S-R 的杂环硫化物，其制备工艺，特别是其在免疫刺激、免疫增强和细胞抑制治疗中的用途，以及用于这些适应症的含有此类硫化物的药物组合物。
• El-Bardan, Ali A.; Hamed, Ezzat A.; Aboul-Ela, Salah L., Journal of the Indian Chemical Society, 1997, vol. 74, # 7, p. 575 - 578
  作者：El-Bardan, Ali A.、Hamed, Ezzat A.、Aboul-Ela, Salah L.、Moussa, Adel M.

  DOI：——

  日期：——
• Luminescent 2D supramolecular network constructed from tubular coordination polymer based on H-bonding and π–π interactions
  作者：Lei Han、Yaqiong Gong、Daqiang Yuan、Maochun Hong

  DOI：10.1016/j.molstruc.2005.12.032

  日期：2006.5

  A novel cadmium(H) coordination polymers, [Cd(bitmb)(2)center dot H2O], (1) (Hbitmb=4-(2-benzimidazolethiomethyl)benzoic acid) has been synthesized under hydrothermal conditions, and characterized by elemental analysis and IR spectra. X-ray diffraction analyses show that 1 is a 1D tubular structure, which is further assembled to 2D supramolecular network by H-bonding and pi-pi interactions. I is luminescent and displays an emissive maximum at 450 nm in the solid state at room temperature. (c) 2006 Elsevier B.V. All rights reserved.