R-(-)-2-α-hydroxybenzylbenzimidazole | 148-38-9

• 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: R-(-)-2-α-hydroxybenzylbenzimidazole
• 英文别名: D(-)-2-α-hydroxybenzylbenzimidazole；(R)-1H-benzimidazol-2-yl(phenyl)methanol
• CAS: 148-38-9
• 化学式: C₁₄H₁₂N₂O
• mdl: MFCD00159953
• 分子量: 224.262
• InChiKey: JEAWPIKEEQZLJQ-CYBMUJFWSA-N

物化性质

• 沸点：
  500.6±43.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氯化镓 、 R-(-)-2-α-hydroxybenzylbenzimidazole 以 乙醚 为溶剂， 以45%的产率得到dichloro-(2-α-oxybenzylbenzimidazolato-N,O)gallium(III)
  参考文献：
  名称：

  Synthesis and characterization of potential antitumour and antiviral gallium(III) complexes of N-heterocycles

  摘要：

  Ten water-soluble gallium(III) complexes of N-heterocycles were synthesized and characterized by elemental analysis, conductivity measurements, IR spectroscopy, H-1 NMR spectroscopy and optical activity measurements. Raman spectra were measured with two complexes and an X-ray single-crystal study performed with one complex-trans-dichlorotetrakis-(5-methylpyrazole)gallium(III)tetrachlorogallate(III). The gallium(III) complexes had the general formulae: [L4GaCl2]GaCl4 (L = ligand) (L = indazole, 1,2,3-benzotriazole, pyrazole, 5-methylpyrazole, 4-methylpyrazole), having a trans-octahedral structure (symmetry C(i)), [L4GaCl2]Cl (L = imidazole, benzimidazole), also with a trans-octahedral configuration, and LGaCl2 (L = 2-alpha-oxybenzylbenzimidazolato (HBB) and the respective enantiomers D(-)-HBB and L(+)-HBB) having a tetrahedral structure.So far, eight gallium(III) complexes have been tested in the in vitro anti-HIV test (HIV = human immunodeficiency virus) of the National Cancer Institute (NCI) in the U.S.A., and four of these were found to be moderately active: trans-dichlorotetrakis(5-methylpyrazole)gallium(III) tetrachlorogallate(III), trans-dichlorotetrakis-(4-methylpyrazole)gallium(III)tetrachlorogallate(III), dichloro-(2-alpha-oxybenzylbenzimidazolato-N,O) gallium (III) and trans-dichlorotetrakis(benzimidazole)gallium(III) chloride, the latter exhibiting the highest therapeutic index (TI) of 77. For comparison, the therapeutic index for 3'-azido-3'-deoxythymidine (AZT) ranges from TI = 1000 to 4000.

  DOI：

  10.1016/s0277-5387(00)83206-4
• 作为产物：
  描述：

  D-扁桃酸 、 邻苯二胺 在 盐酸 作用下， 反应 3.0h， 以45.86%的产率得到R-(-)-2-α-hydroxybenzylbenzimidazole
  参考文献：
  名称：

  Synthesis, in vitro cytotoxic and antiviral activity of cis-[Pt(R(–) and S(+)-2-α-hydroxybenzylbenzimidazole)2Cl2] complexes

  摘要：

  A pair of enantiomeric platinum(II) complexes of cis-[Pt(R(-) and S(+)-HBB)(2)Cl-2] (HBB = 2-alpha-hydroxybenzylbenzimidazole) was synthesized and evaluated for its preliminary in vitro cytotoxic activity on the human MCF-7 breast cancer and HeLa cervix cancer cell lines and antiherpes virus activity against bovine herpesvirus type 1 (BHV-1). In general, it was found that Pt(II) complexes were less cytotoxic on both cell lines than cisplatin and were comparable to carboplatin. There was no significant difference in cytotoxicity between two enantiomers, and the antiviral test results showed that the Pt(II) complexes and their carrier ligands R(-) and S(+) HBB had no effects inhibiting replication of BHV-1. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.09.017

文献信息

• Synthesis, in vitro cytotoxic and antiviral activity of cis-[Pt(R(–) and S(+)-2-α-hydroxybenzylbenzimidazole)2Cl2] complexes
  作者：M. Gökçe、S. Utku、S. Gür、A. Özkul、F. Gümüş

  DOI：10.1016/j.ejmech.2004.09.017

  日期：2005.2

  A pair of enantiomeric platinum(II) complexes of cis-[Pt(R(-) and S(+)-HBB)(2)Cl-2] (HBB = 2-alpha-hydroxybenzylbenzimidazole) was synthesized and evaluated for its preliminary in vitro cytotoxic activity on the human MCF-7 breast cancer and HeLa cervix cancer cell lines and antiherpes virus activity against bovine herpesvirus type 1 (BHV-1). In general, it was found that Pt(II) complexes were less cytotoxic on both cell lines than cisplatin and were comparable to carboplatin. There was no significant difference in cytotoxicity between two enantiomers, and the antiviral test results showed that the Pt(II) complexes and their carrier ligands R(-) and S(+) HBB had no effects inhibiting replication of BHV-1. (C) 2004 Elsevier SAS. All rights reserved.
• Synthesis and characterization of potential antitumour and antiviral gallium(III) complexes of N-heterocycles
  作者：F. Kratz、B. Nuber、J. Weiß、B.K. Keppler

  DOI：10.1016/s0277-5387(00)83206-4

  日期：1992.1

  Ten water-soluble gallium(III) complexes of N-heterocycles were synthesized and characterized by elemental analysis, conductivity measurements, IR spectroscopy, H-1 NMR spectroscopy and optical activity measurements. Raman spectra were measured with two complexes and an X-ray single-crystal study performed with one complex-trans-dichlorotetrakis-(5-methylpyrazole)gallium(III)tetrachlorogallate(III). The gallium(III) complexes had the general formulae: [L4GaCl2]GaCl4 (L = ligand) (L = indazole, 1,2,3-benzotriazole, pyrazole, 5-methylpyrazole, 4-methylpyrazole), having a trans-octahedral structure (symmetry C(i)), [L4GaCl2]Cl (L = imidazole, benzimidazole), also with a trans-octahedral configuration, and LGaCl2 (L = 2-alpha-oxybenzylbenzimidazolato (HBB) and the respective enantiomers D(-)-HBB and L(+)-HBB) having a tetrahedral structure.So far, eight gallium(III) complexes have been tested in the in vitro anti-HIV test (HIV = human immunodeficiency virus) of the National Cancer Institute (NCI) in the U.S.A., and four of these were found to be moderately active: trans-dichlorotetrakis(5-methylpyrazole)gallium(III) tetrachlorogallate(III), trans-dichlorotetrakis-(4-methylpyrazole)gallium(III)tetrachlorogallate(III), dichloro-(2-alpha-oxybenzylbenzimidazolato-N,O) gallium (III) and trans-dichlorotetrakis(benzimidazole)gallium(III) chloride, the latter exhibiting the highest therapeutic index (TI) of 77. For comparison, the therapeutic index for 3'-azido-3'-deoxythymidine (AZT) ranges from TI = 1000 to 4000.