1-(3-Chloro-benzyl)-5,6-dimethyl-1H-benzoimidazole | 141211-38-3

• 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: 1-(3-Chloro-benzyl)-5,6-dimethyl-1H-benzoimidazole
• 英文别名: 1-[(3-Chlorophenyl)methyl]-5,6-dimethylbenzimidazole
• CAS: 141211-38-3
• 化学式: C₁₆H₁₅ClN₂
• 分子量: 270.762
• InChiKey: JVUNQCQURGBZTF-UHFFFAOYSA-N

物化性质

• 沸点：
  448.6±47.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-Chloro-benzyl)-5,6-dimethyl-1H-benzoimidazole 在 palladium diacetate 、 copper (I) acetate 、 copper(II) acetate monohydrate 、 cesium pivalate 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以24%的产率得到2-chloro-7,8-dimethyl-11H-isoindolo[2,1-a]benzimidazole
  参考文献：
  名称：

  Intramolecular arylation of benzimidazoles via Pd(II)/Cu(I) catalyzed cross-dehydrogenative coupling

  摘要：

  Electron poor benzimidazole substrates were arylated via an intramolecular cross-dehydrogenative coupling (CDC) reaction. These CDC reactions were catalyzed by a Pd(II)/Cu(I) catalyst system, capable of producing moderate yields on a large library of substrates. The substrate scope consisted of tethered arene-benzimidazoles that upon coupling, produced a fused polycyclic motif. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.103
• 作为产物：
  描述：

  5,6-二甲基苯并咪唑 、 3-氯苄溴 在 sodium hydride 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 1-(3-Chloro-benzyl)-5,6-dimethyl-1H-benzoimidazole
  参考文献：
  名称：

  The benzimidazole based drugs show good activity against T. gondii but poor activity against its proposed enoyl reductase enzyme target

  摘要：

  The enoyl acyl-carrier protein reductase (ENR) enzyme of the apicomplexan parasite family has been intensely studied for antiparasitic drug design for over a decade, with the most potent inhibitors targeting the NAD(+) bound form of the enzyme. However, the higher affinity for the NADH co-factor over NAD(+) and its availability in the natural environment makes the NADH complex form of ENR an attractive target. Herein, we have examined a benzimidazole family of inhibitors which target the NADH form of Francisella ENR, but despite good efficacy against Toxoplasma gondii, the IC50 for T. gondii ENR is poor, with no inhibitory activity at 1 μM. Moreover similar benzimidazole scaffolds are potent against fungi which lack the ENR enzyme and as such we believe that there may be significant off target effects for this family of inhibitors.

  DOI：

  10.1016/j.bmcl.2013.12.066

文献信息

• Vlaovic, Djordje; Canadanovic-Brunet, Jasna; Balaz, Jelica, Bioscience, Biotechnology and Biochemistry, 1992, vol. 56, # 2.3.4., p. 199 - 206
  作者：Vlaovic, Djordje、Canadanovic-Brunet, Jasna、Balaz, Jelica、Juranic, Ivan、Djokovic, Dejan、Mackenzie, Kenneth

  DOI：——

  日期：——
• Intramolecular arylation of benzimidazoles via Pd(II)/Cu(I) catalyzed cross-dehydrogenative coupling
  作者：Kyle C. Pereira、Ashley L. Porter、Brenton DeBoef

  DOI：10.1016/j.tetlet.2014.01.103

  日期：2014.3

  Electron poor benzimidazole substrates were arylated via an intramolecular cross-dehydrogenative coupling (CDC) reaction. These CDC reactions were catalyzed by a Pd(II)/Cu(I) catalyst system, capable of producing moderate yields on a large library of substrates. The substrate scope consisted of tethered arene-benzimidazoles that upon coupling, produced a fused polycyclic motif. (C) 2014 Elsevier Ltd. All rights reserved.
• The benzimidazole based drugs show good activity against T. gondii but poor activity against its proposed enoyl reductase enzyme target
  作者：Craig Wilkinson、Martin J. McPhillie、Ying Zhou、Stuart Woods、Gustavo A. Afanador、Shaun Rawson、Farzana Khaliq、Sean T. Prigge、Craig W. Roberts、David W. Rice、Rima McLeod、Colin W. Fishwick、Stephen P. Muench

  DOI：10.1016/j.bmcl.2013.12.066

  日期：2014.2

  The enoyl acyl-carrier protein reductase (ENR) enzyme of the apicomplexan parasite family has been intensely studied for antiparasitic drug design for over a decade, with the most potent inhibitors targeting the NAD(+) bound form of the enzyme. However, the higher affinity for the NADH co-factor over NAD(+) and its availability in the natural environment makes the NADH complex form of ENR an attractive target. Herein, we have examined a benzimidazole family of inhibitors which target the NADH form of Francisella ENR, but despite good efficacy against Toxoplasma gondii, the IC50 for T. gondii ENR is poor, with no inhibitory activity at 1 μM. Moreover similar benzimidazole scaffolds are potent against fungi which lack the ENR enzyme and as such we believe that there may be significant off target effects for this family of inhibitors.