methyl 2-(2-methyl-1H-benzimidazol-1-yl)acetate | 2033-54-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(2-methyl-1H-benzimidazol-1-yl)acetate
• 英文别名: Methyl-<2-methyl-1-benzimidazolyl>-acetat；(2-methyl-benzoimidazol-1-yl)-acetic acid methyl ester；methyl (2-methyl-1H-benzimidazol-1-yl)acetate；methyl 2-(2-methylbenzimidazol-1-yl)acetate
• CAS: 2033-54-7
• 化学式: C₁₁H₁₂N₂O₂
• mdl: MFCD05997543
• 分子量: 204.228
• InChiKey: MAUWOBKXBDKYQX-UHFFFAOYSA-N

物化性质

• 熔点：
  117-119 °C
• 沸点：
  362.5±25.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-甲基苯并咪唑 、 溴乙酸甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以43%的产率得到methyl 2-(2-methyl-1H-benzimidazol-1-yl)acetate
  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

• [EN] SUBSTITUTED BENZIMIDAZOLIUM, PYRIDO-IMIDAZOLIUM, OR PYRAZINO-IMIDAZOLIUM COMPOUNDS AS CHEMOTHERAPEUTICS<br/>[FR] COMPOSÉS DE BENZIMIDAZOLIUM, PYRIDO-IMIDAZOLIUM OU PYRAZINO-IMIDAZOLIUM SUBSTITUÉS UTILISÉS COMME AGENTS CHIMIOTHÉRAPEUTIQUES
  申请人：UNIV TEXAS

  公开号：WO2017100525A1

  公开（公告）日：2017-06-15

  Provided herein are compounds of the formula:(I) wherein: R1, R2, R3, R4, R5, X, A1, A2, A3, and A4 are as defined herein. In some aspects, these compounds may be used to treat cancer and other hyperproliferative disease. In some aspects, compositions, methods of treatment, and methods of synthesis are also provided herein.

  本文提供了以下公式的化合物：(I)其中：R1、R2、R3、R4、R5、X、A1、A2、A3和A4的定义如本文所述。在某些方面，这些化合物可用于治疗癌症和其他过度增殖性疾病。在某些方面，本文还提供了组合物、治疗方法和合成方法。
• IMIDAZO[1,2-a]PYRIDINE COMPOUNDS
  申请人：Fang Qun Kevin

  公开号：US20110166146A1

  公开（公告）日：2011-07-07

  Imidazo[1,2-a]pyridines are disclosed. Compounds of the invention are useful therapeutic agents and their inclusion in pharmaceutical formulations and use in methods of treatment are disclosed.

  本发明揭示了咪唑并[1,2-a]吡啶类化合物。该发明的化合物是有用的治疗剂，揭示了它们在制药配方中的包含以及在治疗方法中的使用。
• Research in the imidazole series. 93. Synthesis of derivatives of benzimidazolyl-1-acetic acid
  作者：P. M. Kochergin、R. M. Palei、S. A. Chernyak

  DOI：10.1007/bf00534469

  日期：1993.5
• Research in the imidazole series. 94. Synthesis of derivatives of pyrrolo[1,2a]benzimidazolyl-4-acetic acid
  作者：P. M. Kochergin、R. M. Palei、S. A. Chernyak

  DOI：10.1007/bf00534470

  日期：1993.5
• US8497278B2
  申请人：——

  公开号：US8497278B2

  公开（公告）日：2013-07-30