1-[(4-甲基苯基)甲基]苯并咪唑-2-胺 | 37743-74-1

• 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-[(4-甲基苯基)甲基]苯并咪唑-2-胺
• 英文名称: 1-(4-methylbenzyl)-2-aminobenzimidazole
• 英文别名: 2-amino-1-(4-methylbenzyl)benzimidazole；1-(4-methyl-benzyl)-1H-benzoimidazol-2-ylamine；1-(4-Methyl-benzyl)-1H-benzoimidazol-2-ylamine；1-[(4-methylphenyl)methyl]benzimidazol-2-amine
• CAS: 37743-74-1
• 化学式: C₁₅H₁₅N₃
• mdl: MFCD01051390
• 分子量: 237.304
• InChiKey: HUXAXCIUQJSPOG-UHFFFAOYSA-N

物化性质

• 沸点：
  462.0±48.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于CHCl3、DCM、MeOH、丙酮、乙腈

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.133
• 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：

  溴代十二烷 、 1-[(4-甲基苯基)甲基]苯并咪唑-2-胺 以 丁酮 为溶剂， 反应 48.0h， 以95%的产率得到2-amino-3-dodecyl-1-(4-methylbenzyl)-1H-3,1-benzimidazole bromide
  参考文献：
  名称：

  杂环双阳离子是设计枯草芽孢杆菌双功能酶含组氨酸的蛋白激酶/磷酸酶抑制剂的起点。

  摘要：

  在低鸟嘌呤和低胞嘧啶革兰氏阳性细菌中碳分解代谢物阻遏/激活的主要机制似乎涉及到ATP依赖性HPr激酶在Ser-46处HPr（含组氨酸的蛋白）的磷酸化，该酶在枯草芽孢杆菌中，干酪乳杆菌和木糖葡萄球菌也具有磷酸酶活性，因此是一种双功能酶（HPrK / P）。由于木糖链球菌，干酪乳杆菌和枯草芽孢杆菌突变体中HPrK / P的缺乏会导致严重的生长缺陷，因此该酶的抑制剂可能会形成一个新的抗生素药物家族。这项研究的目的是筛选一个内部化学文库，以鉴定作为枯草芽孢杆菌中HPrK / P抑制剂的命中物，并使用放射性体外测定法从命中优化中进一步提取结构特征的其他信息。对称的双阳离子化合物LPS 02-10-L-D09（2a）具有桥接两个2-氨基苯并咪唑部分的12个碳原子的烷基连接基，被确定为具有10 microM的EC（50）值的非ATP模拟化合物在以HPr为底物的激酶测定中 该物质还抑制了添加无机磷酸盐后触发的HPrK

  DOI：

  10.1021/jm021043o
• 作为产物：
  描述：

  2-氨基苯并咪唑 、 4-甲基氯苄 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以53.4%的产率得到1-[(4-甲基苯基)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

• Regioselective N-Alkylation of 2-Aminoimidazoles with Alcohols to 2-(N-Alkylamino)imidazoles Catalyzed by the [Cp*IrCl2]2/K2CO3 System
  作者：Feng Li、Qikai Kang、Haixia Shan、Lin Chen、Jianjiang Xie

  DOI：10.1002/ejoc.201200698

  日期：2012.9

  The direct N-alkylation of 2-aminoimidazoles to give the corresponding 2-(N-alkylamino)imidazoles was accomplished using alcohols as alkylating agents in the presence of a [Cp*IrCl2]2/K2CO3 system. The iridium-catalyzed regioselective reaction is simple, efficient, general, and environmentally benign.

  在 [Cp*IrCl2]2/K2CO3 系统存在下，使用醇作为烷基化剂，完成 2-氨基咪唑的直接 N-烷基化以得到相应的 2-(N-烷基氨基)咪唑。铱催化的区域选择性反应简单、高效、通用且对环境无害。
• Generation of 500-Member Library of 10-Alkyl-2-R1,3-R2-4,10-Dihydrobenzo[4,5]imidazo[1,2-α]pyrimidin-4-ones
  作者：Svetlana Sirko、Nikolay Yu. Gorobets、Vladimir Musatov、Sergey Desenko

  DOI：10.3390/molecules14125223

  日期：——

  Representative benzimidazopyrimidinones were previously reported to be intercalating antitumor agents. In this work, we used 2-substituted 4,10-dihydrobenzo [4,5]imidazo[1,2-α]pyriminin-4-ones for their diversification by regioselective alkylation. Under the conditions established, the alkylation gave 10-alkyl derivatives which permitted the parallel generation of a 500-member library of the title compounds.

  代表性苯并咪唑吡啶酮之前被报道为插层抗肿瘤剂。在本研究中，我们使用了2取代的4,10-二氢苯并[4,5]咪唑[1,2-α]吡咯啉-4-酮，通过区域选择性烷基化进行多样化。在设定的条件下，烷基化生成的10-烷基衍生物使得能够并行生成一个500个成员的标题化合物库。
• 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：——
• 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：——