1-苯基-5-羟基苯并咪唑 | 69445-45-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1-苯基-5-羟基苯并咪唑
• 英文名称: 1-phenyl-1H-benzo[d]imidazol-5-ol
• 英文别名: 1-phenyl-1H-benzimidazol-5-ol；5-hydroxy-1-phenylbenzimidazole；1-Phenyl-5-hydroxybenzimidazole；1-phenylbenzimidazol-5-ol
• CAS: 69445-45-0
• 化学式: C₁₃H₁₀N₂O
• 分子量: 210.235
• InChiKey: OQAPWZCMAFFBBL-UHFFFAOYSA-N

物化性质

• 沸点：
  430.7±37.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-苯基-5-羟基苯并咪唑 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以75%的产率得到4-Bromo-5-hydroxy-1-phenylbenzimidazole
  参考文献：
  名称：

  Structure−Activity Relationships for 5-Substituted 1-Phenylbenzimidazoles as Selective Inhibitors of the Platelet-Derived Growth Factor Receptor

  摘要：

  Following an earlier discovery of 1-phenylbenzimidazoles as ATP-site inhibitors of the platelet-derived growth factor receptor (PDGFR), further structure-activity relationships for analogues (particularly 5-substituted derivatives) are reported. The data are consistent with a binding model (constructed from the homology-modeled structure of the catalytic subunit of the PDGFR using protein kinase A as the template) in which the ligand binds in the relatively narrow ATP site, with the phenyl ring pointing toward the interior of the pocket and the 5-position of the benzimidazole ring toward the mouth of the pocket. The narrow binding pocket allows a maximum torsion angle between the phenyl and benzimidazole rings of about 40 degrees, consistent with that calculated (43.6 degrees) for the minimum-energy conformation of the unsubstituted free ligand. The inactivity of 7- or 2'-substituted analogues is consistent with the greater torsion angle (and thus larger ligand cross-section) of such substituted analogues. There is substantial bulk tolerance for 5-substituents, which protrude out of the mouth of the hydrophobic pocket, with the most effective analogues being those bearing weak bases. On the basis of this model, 5-OR derivatives bearing cationic side chains were prepared as soluble analogues, and these showed sub-micromolar potencies against the isolated PDGFR enzyme. They were also moderately effective inhibitors of autophosphorylation of PDGFR in rat aortic vascular smooth muscle cells, with IC(50)s in the range 0.1-1 mu 1M.

  DOI：

  10.1021/jm980658b
• 作为产物：
  描述：

  4-methoxy-2-nitro-N-phenylaniline 在 palladium 10% on activated carbon 、 氢气 、 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 、 乙二醇甲醚 为溶剂， -78.0~80.0 ℃ 、101.33 kPa 条件下， 反应 17.0h， 生成 1-苯基-5-羟基苯并咪唑
  参考文献：
  名称：

  新型雷帕霉素哺乳动物雷帕霉素靶标抑制剂的鉴定

  摘要：

  我们使用内部小分子文库对mTOR进行了生化筛选。确定了两个新颖的，结构上不同的命中。其中，新型的恶二唑支架化合物（2）抑制了HeLa细胞中S6K1和Akt1的磷酸化。对接研究表明2具有ATP竞争性，并显示与Trp2239的pi-pi相互作用以及与Trp2239和Thr2245的氢键。通过衍生化，鉴定出稍微更有效的类似物（2a），IC 50为9.6μM。我们的研究为发现新型有效的mTOR抑制剂提供了一个起点。

  DOI：

  10.1002/bkcs.11965

文献信息

• Benzimidazoles for inhibiting protein tyrosine kinase mediated cellular
  申请人：Warner-Lambert Company

  公开号：US05990146A1

  公开（公告）日：1999-11-23

  Benzimidazoles of Formula I below are inhibitors of protein tyrosine kinases, and are useful in treating cellular proliferation. ##STR1## The compounds are especially useful in treating cancer, atherosclerosis, restenosis, and psoriasis.

  下面的I式苯并咪唑是蛋白酪氨酸激酶的抑制剂，对治疗细胞增殖很有用。这些化合物在治疗癌症、动脉粥样硬化、再狭窄和牛皮癣方面特别有效。
• Benzimidazoles for inhibiting protein tyrosine kinase mediated cellular proliferation
  申请人：Warner-Lambert Company

  公开号：US06218388B1

  公开（公告）日：2001-04-17

  Benzimidazoles of Formula I below are inhibitors of protein tyrosine kinases, and are useful in treating cellular proliferation. The compounds are especially useful in treating cancer, atherosclerosis, restenosis, and psoriasis.

  以下式I的苯并咪唑化合物是蛋白质酪氨酸激酶的抑制剂，可用于治疗细胞增殖。这些化合物在治疗癌症、动脉粥样硬化、再狭窄和银屑病方面特别有用。
• NOVEL MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS REPLICATION
  申请人：Buckman Brad

  公开号：US20110081315A1

  公开（公告）日：2011-04-07

  The embodiments provide compounds of the general Formulae I, Ia, II, III, IV, V, VI-1, VI-2, VII, VIII, IX, X, XI, and XII, as well as compositions, including pharmaceutical compositions, comprising a subject compound. The embodiments further provide treatment methods, including methods of treating a hepatitis C virus infection and methods of treating liver fibrosis, the methods generally involving administering to an individual in need thereof an effective amount of a subject compound or composition.

  本实施例提供了一般式I、Ia、II、III、IV、V、VI-1、VI-2、VII、VIII、IX、X、XI和XII的化合物，以及包括药物组合物在内的组合物。本实施例还提供了治疗方法，包括治疗丙型肝炎病毒感染的方法和治疗肝纤维化的方法，这些方法通常涉及向需要该化合物或组合物的个体施用有效量的该化合物或组合物。
• Tyrosine Kinase Inhibitors
  申请人：Dinsmore Christopher J.

  公开号：US20090149467A1

  公开（公告）日：2009-06-11

  The present invention relates to pyridinyloxy- and pyrimidinyloxyindole derivatives, that are useful for treating cellular proliferative diseases, for treating disorders associated with MET activity, and for inhibiting the receptor tyrosine kinase MET. The invention also related to compositions which comprise these compounds, and methods of using them to treat cancer in mammals.

  本发明涉及吡啶氧基和嘧啶氧基吲哚衍生物，其用于治疗细胞增殖性疾病，用于治疗与MET活性相关的疾病，并用于抑制受体酪氨酸激酶MET。本发明还涉及包含这些化合物的组合物和使用它们治疗哺乳动物癌症的方法。
• Fries, Justus Liebigs Annalen der Chemie, 1927, vol. 454, p. 204
  作者：Fries

  DOI：——

  日期：——