2-(2-methyl-1H-benzimidazol-1-yl)acetohydrazide | 97420-40-1

• 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: 2-(2-methyl-1H-benzimidazol-1-yl)acetohydrazide
• 英文别名: 2-(2-methylbenzimidazol-1-yl)acetohydrazide
• CAS: 97420-40-1
• 化学式: C₁₀H₁₂N₄O
• mdl: MFCD00227235
• 分子量: 204.231
• InChiKey: VUMSWGDUJKYNFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(2-methyl-1H-benzimidazol-1-yl)acetohydrazide 在 氢氧化钾 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 13.0h， 生成 4-amino-5-[(2-methyl-1H-benzimidazol-1-yl)methyl]-4H-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  Habib, Nargues S.; Soliman; Ashour, Pharmazie, 1997, vol. 52, # 11, p. 844 - 847

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2-(2-methyl-1H-benzimidazol-1-yl)acetate 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以92%的产率得到2-(2-methyl-1H-benzimidazol-1-yl)acetohydrazide
  参考文献：
  名称：

  Structure–Activity Studies of Divin: An Inhibitor of Bacterial Cell Division

  摘要：

  We describe the synthesis and structure activity relationship (SAR) studies of divin, a small molecule that blocks bacterial division by perturbing the assembly of proteins at the site of cell septation. The bacteriostatic mechanism of action of divin is distinct from other reported inhibitors of bacterial cell division and provides an opportunity for assessing the therapeutic value of a new class of antimicrobial agents. We demonstrate a convenient synthetic route to divin and its analogues, and describe compounds with a 10-fold increase in solubility and a 4-fold improvement in potency. Divin analogues produce a phenotype that is identical to divin, suggesting that their biological activity comes from a similar mechanism of action. Our studies indicate that the 2-hydroxynaphthalenyl hydrazide portion of divin is essential for its activity and that alterations and substitution to the benzimidazole ring can increase its potency. The SAR study provides a critical opportunity to isolate drug resistant mutants and synthesize photoaffinity probes to determine the cellular target and biomolecular mechanism of divin.

  DOI：

  10.1021/ml400234x

文献信息

• Synthesis and Antibacterial Activity of Some Derivatives of 2-Methylbenzimidazole Containing 1,3,4-Oxadiazole or 1,2,4-Triazole Heterocycle
  作者：Cong Nguyen Tien、Duc Tran Thi Cam、Ha Bui Manh、Dat Nguyen Dang

  DOI：10.1155/2016/1507049

  日期：——

  respectively. The structures of the compounds were elucidated on the basis of IR, MS, 1H-NMR, and 13C-NMR spectral data. The compounds containing 1,3,4-oxadiazole or 1,2,4-triazole heterocycle also were tested for their antimicrobial activity against bacteria, mold, and yeast.

  5-[(2-Methyl-1H-benzimidazol-1-yl)methyl]-1,3,4-oxadiazole-2-thiol or 5-[(2-methyl-1H-benzimidazol-1-yl)methyl]- 4-(4-甲基苯基)-1,2,4-三唑-3-硫醇以2-甲基苯并咪唑为原料，与合适的N-芳基-2-氯乙酰胺反应得到两个系列的N-芳基-2-5 -[(2-甲基-1H-苯并咪唑-1-基)甲基]-1,3,4-恶二唑-2-基硫烷基乙酰胺和N-芳基-2-5-[(2-甲基-1H-苯并咪唑-1-基)甲基]-4-(4-甲基苯基)-4H-1,2,4-三唑-3-基硫代乙酰胺。基于IR、MS、1H-NMR和13C-NMR光谱数据阐明了化合物的结构。还测试了含有 1,3,4-恶二唑或 1,2,4-三唑杂环的化合物对细菌、霉菌和酵母的抗菌活性。
• Synthesis and biological activity of some triazole-bearing benzimidazole derivatives
  作者：K.F. Ansari、C. Lal、R.K. Khitoliya

  DOI：10.2298/jsc100301029a

  日期：——

  A number of N'-[(aryl)methylidene]-2-(2-methyl-1H-benzimidazol- 1-yl)acetohydrazide and 4-(aryl)-5-[(2-methyl-1H-benzimidazol- 1-yl)methyl]-4H-1,2,4-triazole-3-thiol derivatives were synthesized by incorporating various aromatic and heterocyclic substituents on 2-methyl-1H-benzimidazole. The structures of all the synthesized compounds were elucidated based on their elemental analyses and spectral data. The in vitro activities of these compounds against bacteria and fungi were evaluated by the disc diffusion and the minimum inhibitory concentration (MIC) methods. Some of the synthesized derivatives were found to be as active as kanamycin (standard drug).

  一些 N'-[（芳基）亚甲基]-2-（2-甲基-1H-苯并咪唑- 1-基)乙酰肼和 4-(芳基)-5-[(2-甲基-1H-苯并咪唑- 1-基)甲基]-4H-1,2,4-三唑-3-硫醇衍生物的合成。 在 2-甲基-1H-苯并咪唑-1-基上加入各种芳香族和杂环取代基，合成了 2-甲基-1H-苯并咪唑。所有合成化合物的结构 根据元素分析和光谱数据阐明了所有合成化合物的结构。这些化合物的 对细菌和真菌的体外活性进行了评估。 盘扩散法和最低抑菌浓度 (MIC) 法评估了这些化合物对细菌和真菌的体外活性。 发现一些合成衍生物的活性与卡那霉素（标准药物）相当。 (标准药物）一样有效。
• Synthesis, physicochemical properties and antimicrobial activity of some new benzimidazole derivatives
  作者：K.F. Ansari、C. Lal

  DOI：10.1016/j.ejmech.2009.04.037

  日期：2009.10

  spectral and elemental methods of analyses. All the synthesized compounds were screened for their antimicrobial activities. All of the derivatives showed good activity towards Gram-positive bacteria and negligible activity towards Gram-negative bacteria. Some of the synthesized compounds showed moderate activity against tested fungi.

  苯并咪唑的一些衍生物是通过2-取代-1 H-苯并咪唑的亲核取代反应合成的。将得到的乙基（2-取代- 1 ħ苯并咪唑-1-基）乙酸甲酯与水合肼处理，得到2-（2-取代的-1- ħ苯并咪唑-1-基）乙酰肼，其在进一步的反应与一当量的在磷酰氯存在下，用不同的脂族或芳族羧酸制得相应的目标化合物2-取代的-1-[（（5-取代的烷基/芳基）-1,3,4-恶二唑-2-基}甲基]- 1小时-苯并咪唑。通过光谱和元素分析法评估了合成化合物的结构。筛选所有合成的化合物的抗菌活性。所有的衍生物对革兰氏阳性菌均表现出良好的活性，而对革兰氏阴性菌则表现为微不足道的活性。一些合成的化合物显示出对测试真菌的中等活性。
• Synthesis of benzimidazole based thiadiazole and carbohydrazide conjugates as glycogen synthase kinase-3β inhibitors with anti-depressant activity
  作者：Imran Khan、Mushtaq A. Tantray、Hinna Hamid、Mohammad Sarwar Alam、Abul Kalam、Abhijeet Dhulap

  DOI：10.1016/j.bmcl.2016.06.084

  日期：2016.8

  A series of benzimidazole based thiadiazole and carbohydrazide conjugates have been synthesized and evaluated for inhibition of glycogen synthase kinase-3β and anti-depressant effect. Compounds 4f, 4j, 5b, 5g and 5i were found to be the most potent inhibitors of GSK-3β in vitro amongst the twenty-five benzimidazole based thiadiazole and carbohydrazide conjugates synthesized. Compound 5i was also found

  已经合成了一系列基于苯并咪唑的噻二唑和碳酰肼共轭物，并评估了其对糖原合酶激酶-3β的抑制作用和抗抑郁作用。在合成的二十五种基于苯并咪唑的噻二唑和碳酰肼共轭物中，发现化合物4f，4j，5b，5g和5i是体外最有效的GSK-3β抑制剂。化合物5i当与已知的抗抑郁药氟西汀相比时，氟吡西汀还被发现在50 mg / kg的体内具有显着的抗抑郁活性。分子对接研究揭示了合成的化合物与多种氨基酸残基（即GSK-3β上的ASP-133，LYS-183，PRO-136，VAL-135，TYR-134或LYS-60）的多个氢键相互作用。受体部位。
• Shetgiri; Kokitkar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 2, p. 163 - 166
  作者：Shetgiri、Kokitkar

  DOI：——

  日期：——