1-[(3-氯苯基)甲基]苯并咪唑-2-胺 | 141472-88-0

• 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-[(3-氯苯基)甲基]苯并咪唑-2-胺
• 英文名称: 1-(3-chlorobenzyl)- 2-aminobenzimidazole
• 英文别名: 1-[(3-Chlorophenyl)methyl]-1H-benzimidazol-2-amine；1-[(3-chlorophenyl)methyl]benzimidazol-2-amine
• CAS: 141472-88-0
• 化学式: C₁₄H₁₂ClN₃
• mdl: MFCD17527312
• 分子量: 257.722
• InChiKey: VXCWJWHHHGVVFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(3-氯苯基)甲基]苯并咪唑-2-胺 、 氯甲酸苯酯 在 potassium iodide 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以64%的产率得到
  参考文献：
  名称：

  Kranthi Kumar; Laxminarayana; Thirupathaiah, Indian Journal of Heterocyclic Chemistry, 2013, vol. 23, # 2, p. 125 - 128

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基苯并咪唑 、 间氯氯苄 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以60.6%的产率得到1-[(3-氯苯基)甲基]苯并咪唑-2-胺
  参考文献：
  名称：

  A novel 2‐aminobenzimidazole‐based compound Jzu 17 exhibits anti‐angiogenesis effects by targeting VEGFR‐2 signalling

  摘要：

  Background and PurposeRecent development in drug discovery have shown benzimidazole to be an important pharmacophore,. Benzimidazole derivatives exhibit broad‐spectrum pharmacological properties including anti‐microbial, anti‐diabetic and anti‐tumour activity. However, whether benzimidazole derivatives are effective in suppressing angiogenesis and its underlying mechanisms remain incompletely understood. In this study, we aim to characterize the anti‐angiogenic mechanisms of a novel 2‐aminobenzimidazole‐based compound, Jzu 17, in an effort to develop novel angiogenesis inhibitor.Experimental ApproachEffects of Jzu 17 on endothelial cell proliferation, migration, invasion, and activation of signalling molecules induced by VEGF‐A, were analysed by immunoblotting, MTT, BrdU, migration, and invasion assays. We performed tube formation assay, aorta ring sprouting assay, matrigel plug assay, and a mouse model of metastasis to evaluate ex vivo and in vivo anti‐angiogenic effects of Jzu 17.Key ResultsJzu 17 inhibited VEGF‐A‐induced cell proliferation, migration, invasion, and endothelial tube formation of HUVECs. Jzu 17 suppressed VEGF‐A‐induced microvessel sprouting ex vivo and attenuated VEGF‐A‐ or tumour cell‐induced neovascularization in vivo. Jzu 17 also reduced B16F10 melanoma lung metastasis. In addition, Jzu 17 inhibited the phosphorylation of VEGFR‐2 and its downstream signalling molecules in VEGF‐A‐stimulated HUVECs. Results from computer modelling further showed that Jzu 17 binds to VEGFR‐2 with high affinity.Conclusions and ImplicationsJzu 17 may inhibit endothelial remodelling and suppress angiogenesis through targeting VEGF‐A‐VEGFR‐2 signalling. These results also suggest Jzu 17 as a potential lead compound and warrant the clinical development of similar agents in the treatment of cancer and angiogenesis‐related diseases.

  DOI：

  10.1111/bph.14813

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：——
• A novel 2‐aminobenzimidazole‐based compound Jzu 17 exhibits anti‐angiogenesis effects by targeting VEGFR‐2 signalling
  作者：Jin‐Cherng Lien、Chi‐Li Chung、Tur‐Fu Huang、Tsung‐Chia Chang、Kuan‐Chung Chen、Ging‐Yan Gao、Ming‐Jen Hsu、Shiu‐Wen Huang

  DOI：10.1111/bph.14813

  日期：2019.10

  Background and PurposeRecent development in drug discovery have shown benzimidazole to be an important pharmacophore,. Benzimidazole derivatives exhibit broad‐spectrum pharmacological properties including anti‐microbial, anti‐diabetic and anti‐tumour activity. However, whether benzimidazole derivatives are effective in suppressing angiogenesis and its underlying mechanisms remain incompletely understood. In this study, we aim to characterize the anti‐angiogenic mechanisms of a novel 2‐aminobenzimidazole‐based compound, Jzu 17, in an effort to develop novel angiogenesis inhibitor.Experimental ApproachEffects of Jzu 17 on endothelial cell proliferation, migration, invasion, and activation of signalling molecules induced by VEGF‐A, were analysed by immunoblotting, MTT, BrdU, migration, and invasion assays. We performed tube formation assay, aorta ring sprouting assay, matrigel plug assay, and a mouse model of metastasis to evaluate ex vivo and in vivo anti‐angiogenic effects of Jzu 17.Key ResultsJzu 17 inhibited VEGF‐A‐induced cell proliferation, migration, invasion, and endothelial tube formation of HUVECs. Jzu 17 suppressed VEGF‐A‐induced microvessel sprouting ex vivo and attenuated VEGF‐A‐ or tumour cell‐induced neovascularization in vivo. Jzu 17 also reduced B16F10 melanoma lung metastasis. In addition, Jzu 17 inhibited the phosphorylation of VEGFR‐2 and its downstream signalling molecules in VEGF‐A‐stimulated HUVECs. Results from computer modelling further showed that Jzu 17 binds to VEGFR‐2 with high affinity.Conclusions and ImplicationsJzu 17 may inhibit endothelial remodelling and suppress angiogenesis through targeting VEGF‐A‐VEGFR‐2 signalling. These results also suggest Jzu 17 as a potential lead compound and warrant the clinical development of similar agents in the treatment of cancer and angiogenesis‐related diseases.
• Kranthi Kumar; Laxminarayana; Thirupathaiah, Indian Journal of Heterocyclic Chemistry, 2013, vol. 23, # 2, p. 125 - 128
  作者：Kranthi Kumar、Laxminarayana、Thirupathaiah、Thirumala Chary

  DOI：——

  日期：——