(1-苄基苯并咪唑-2-基)肼 | 14180-45-1

• 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-苄基苯并咪唑-2-基)肼
• 英文名称: (1-benzyl-2-benzimidazolyl)hydrazine
• 英文别名: 1-benzyl-2-benzimidazolylhydrazine；1-benzyl-2-hydrazinobenzimidazole；1-benzyl-2-hydrazino-1H-benzoimidazole；1-Benzyl-2-hydrazino-benzimidazol；2-Hydrazino-1-benzyl-benzimidazol；(1-benzylbenzimidazol-2-yl)hydrazine
• CAS: 14180-45-1
• 化学式: C₁₄H₁₄N₄
• mdl: MFCD00514559
• 分子量: 238.292
• InChiKey: WOMDKZPPJCZPCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  55.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1-苄基苯并咪唑-2-基)肼 在 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 (10-Benzyl-3,4-dioxo-3,4-dihydro-10H-benzo[4,5]imidazo[2,1-c][1,2,4]triazin-2-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  [1,2,4]Triazino[4,3-a]benzimidazole Acetic Acid Derivatives:  A New Class of Selective Aldose Reductase Inhibitors

  摘要：

  Acetic acid derivatives of [1,2,4]triazino[4,3-alpha ]benzimidazole (TBI) were synthesized and tested in vitro and in vivo as a novel class of aldose reductase (ALR2) inhibitors. Compound 3, (10-benzyl[1,2,4]triazino[4,3-alpha ]benzimidazol-3,4(10H)-dion-2-yl)acetic acid, displayed the highest inhibitory activity (IC50 = 0.36 muM) and was found to be effective in preventing cataract development in severely galactosemic rats when administered as an eyedrop solution. All the compounds investigated were selective for ALR2, since none of them inhibited appreciably aldehyde reductase, sorbitol dehydrogenase, or glutathione reductase. The activity of 3 was lowered by inserting various substituents on the pendant phenyl ring, by shifting the acetic acid moiety from the 2 to the 3 position of the TBI nucleus, or by cleaving the TBI system to yield benzimidazolylidenehydrazines as open-chain analogues. A three-dimensional model of human ALR2 was built, taking into account the conformational. changes induced by the binding of inhibitors such as zopolrestat, to simulate the docking of 3 into the enzyme active site. The theoretical binding mode of 3 was fully consistent with the structure-activity relationships in the TBI series and will guide the design of novel ALR2 inhibitors.

  DOI：

  10.1021/jm0109210
• 作为产物：
  描述：

  1-苄基-2-氯苯并咪唑 在 一水合肼 作用下， 反应 5.0h， 生成 (1-苄基苯并咪唑-2-基)肼
  参考文献：
  名称：

  RETRACTED: Synthesis and biological evaluation of [1,2,4]triazino[4,3-a] benzimidazole acetic acid derivatives as selective aldose reductase inhibitors

  摘要：

  The acetic acid derivatives of [1,2,4]triazino[4,3-a]benzimidazole (TBI) were synthesized and tested in vitro and in vivo as selective aldose reductase (ALR2) inhibitors. Compound PS11 showed highest inhibitory activity (IC50) 0.32 mu M and was found to be effective in preventing cataract development in severely galactosemic rats when administered as an eyedrop solution. All the compounds investigated were selective for ALR2, since none of them inhibited appreciably aldehyde reductase, sorbitol dehydrogenase, or glutathione reductase. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.11.031

文献信息

• Synthesis and anti-influenzaactivity of N-substituted-2-benzazol-2-ylhydrazinocarbothioamides
  作者：G. N. Tyurenkova、V. I. Il'enko、N. V. Serebryakova、V. G. Platonov、G. A. Mokrushina、I. I. Mudretsova

  DOI：10.1007/bf00758277

  日期：1988.3

  Scientific Fundamentals of Antibiotics [in Russian], 3rd edition, Moscow (1979), pp. 46-47~ V. I. ll'enko, Methods of Testing and Assessment of the Antiviral Activity of Chemical Compounds against Influenze Virus. Methodology [in Russian], Leningrad (1977). G. A. Mokrushina, S. K. Kotovskaya, and G. A. Yurchenko, Conference on the Chemistry and Technology of Organic Sulfur Compounds and Sulfur-Containing

  NS Egorov，抗生素科学基础 [俄文]，第 3 版，莫斯科（1979 年），第 46-47 页~ VI ll'enko，化合物抗流感病毒抗病毒活性的测试和评估方法。方法论[俄语]，列宁格勒（1977 年）。GA Mokrushina、SK Kotovskaya 和 GA Yurchenko，有机硫化合物和含硫石油化学与技术会议。第 16 号：论文摘要 [俄文]，里加，1984 年，第 1 页。187. GA Mokrushina、SK Kotovskaya、GN Tyurenkova 等人，Khim.-farm。Zh., No. 2, 195 (1988).
• One-Pot Green Synthesis of 3'-(2-Aminobenzimidazolyl)-2-Phenyl Spiro[4H-Benzopyran-4,2'-Thiazolidin]-4-Ones and Acylation Using Trifluoroacetic Anhydride
  作者：Kanti Sharma、Renuka Jain

  DOI：10.1080/10426507.2011.557574

  日期：2011.10

  Excellent yields (85%–90%) and higher purity are obtained in the ionic-liquid-mediated synthesis as compared with the conventional procedure (55%–60%). Further, these compounds were acylated with trifluoroacetic anhydride. The structures of the compounds were confirmed by IR, 1H NMR, 13C NMR, mass spectral data, and elemental analysis. The compounds, upon evaluation for their antibacterial, antifungal, and

  摘要 通过缩合取代的肼基苯并咪唑实现了一种新型杂环体系 3'-(2-氨基苯并咪唑基)-2-苯基螺[4H-苯并吡喃-4,2'-噻唑烷]-4-酮的快速一锅合成。 、黄烷酮和巯基乙酸通过在乙醇或甲苯中以及在离子液体中常规加热，即六氟磷酸 1-丁基-3-甲基-咪唑鎓。与传统方法 (55%–60%) 相比，离子液体介导的合成获得了优异的产率 (85%–90%) 和更高的纯度。此外，这些化合物用三氟乙酸酐酰化。化合物的结构经IR、1H NMR、13C NMR、质谱数据和元素分析确证。这些化合物在评价其抗菌、抗真菌和杀虫活性时表现出优异的效果。[本文有补充材料。访问出版商的在线版磷、硫和硅及相关元素，获取以下免费补充资源：表 S1、S2 和 S3] 图形摘要
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.7.2.3, page 244 - 263
  作者：

  DOI：——

  日期：——
• Kharchuk, V. G.; Petrov, L. A., Zhurnal Obshchei Khimii, 1978, vol. 48, p. 418 - 419
  作者：Kharchuk, V. G.、Petrov, L. A.

  DOI：——

  日期：——
• Synthesis and structures of alkyl (aryl) benzazolylazoketoximes
  作者：L. I. Medvedeva、G. N. Lipunova、N. P. Bednyagina、I. I. Mudretsova、E. O. Sidorov

  DOI：10.1007/bf00513171

  日期：1980.8