5-(aminomethyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride | 903558-72-5

• 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: 5-(aminomethyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride
• 英文别名: 5-(aminomethyl)-1,3-dihydrobenzimidazol-2-one;hydrochloride
• CAS: 903558-72-5
• 化学式: C₈H₉N₃O*ClH
• mdl: MFCD13186035
• 分子量: 199.64
• InChiKey: NQLRPHFCKRGDGL-UHFFFAOYSA-N

物化性质

• 溶解度：
  >29.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0.27
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  74.67
• 氢给体数：
  3.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+/-)-3-苯基丁酸 、 5-(aminomethyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride 在 N,N'-羰基二咪唑 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以78%的产率得到N-((2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)methyl)-3-phenylbutanamide
  参考文献：
  名称：

  Development of alkyl glycerone phosphate synthase inhibitors: Structure-activity relationship and effects on ether lipids and epithelial-mesenchymal transition in cancer cells

  摘要：

  In aggressive tumors, alkylglyceronephosphate synthase (AGPS) controls cellular ether phospholipid utilization and metabolism to promote cancer cell proliferation and motility. SAR studies on the first-in-class AGPS inhibitor 1, discovered by our group, led to the 2,6-difluoro analog 2i which showed higher binding affinity than 1 in vitro. In 231MFP cancer cells, 2i reduced ether lipids levels and cell migration rate. When tested in PC-3 and MDA-MB-231 cancer cells, 2i specifically impaired epithelial to mesenchymal transition (EMT) by modulating E-cadherin, Snail and MMP2 expression levels. Moreover, the combination of siRNAs against AGPS and 2i provided no additive effect, confirming that the modulation of 2i on EMT specifically relies on AGPS inhibition. Finally, this compound also affected cancer cell proliferation especially in MDA-MB-231 cells expressing higher AGPS level, whereas it provided negligible effects on MeT5A, a non-tumorigenic cell line, thus showing cancer specificity. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.11.050
• 作为产物：
  描述：

  2,3-二氢-2-氧代-1H-苯并咪唑-5-腈 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以74%的产率得到5-(aminomethyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride
  参考文献：
  名称：

  Development of alkyl glycerone phosphate synthase inhibitors: Structure-activity relationship and effects on ether lipids and epithelial-mesenchymal transition in cancer cells

  摘要：

  In aggressive tumors, alkylglyceronephosphate synthase (AGPS) controls cellular ether phospholipid utilization and metabolism to promote cancer cell proliferation and motility. SAR studies on the first-in-class AGPS inhibitor 1, discovered by our group, led to the 2,6-difluoro analog 2i which showed higher binding affinity than 1 in vitro. In 231MFP cancer cells, 2i reduced ether lipids levels and cell migration rate. When tested in PC-3 and MDA-MB-231 cancer cells, 2i specifically impaired epithelial to mesenchymal transition (EMT) by modulating E-cadherin, Snail and MMP2 expression levels. Moreover, the combination of siRNAs against AGPS and 2i provided no additive effect, confirming that the modulation of 2i on EMT specifically relies on AGPS inhibition. Finally, this compound also affected cancer cell proliferation especially in MDA-MB-231 cells expressing higher AGPS level, whereas it provided negligible effects on MeT5A, a non-tumorigenic cell line, thus showing cancer specificity. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.11.050

文献信息

• HETEROCYCLIC COMPOUND HAVING ANTI-HIV ACTIVITY
  申请人：Toyama Chemical Co., Ltd.

  公开号：EP2810944A1

  公开（公告）日：2014-12-10

  A heterocyclic compound represented by the general formula (in the formula, R1, R2 and R3 may be the same or different, and each represents a hydrogen atom, a halogen atom, or this general formula (X1-Y1-R4) (in the formula: X1 represents this general formula (NR5) (in the formula, R5 represents a hydrogen atom, etc.) or the like; Y1 represents an optionally substituted C1-6 alkylene group or the like; and R4 represents an optionally substituted aryl group or the like), and Z represents a nitrogen atom or this general formula (CR6) (in the formula, R6 represents a hydrogen atom, a halogen atom, or an optionally substituted C1-12 alkyl group or the like)), or a salt thereof, exhibits excellent anti-HIV activity and is useful as an anti-HIV agent.

  由一般公式表示的杂环化合物（在公式中，R1、R2和R3可以相同也可以不同，每个表示氢原子、卤原子或这一般式（X1-Y1-R4）（在公式中：X1表示这一般式（NR5）（在公式中，R5表示氢原子等）或类似物；Y1表示可选择地取代的C1-6烷基链或类似物；R4表示可选择地取代的芳基或类似物），Z表示氮原子或这一般式（CR6）（在公式中，R6表示氢原子、卤原子或可选择地取代的C1-12烷基链或类似物）），或其盐，表现出优异的抗HIV活性，并可用作抗HIV剂。
• Development of alkyl glycerone phosphate synthase inhibitors: Structure-activity relationship and effects on ether lipids and epithelial-mesenchymal transition in cancer cells
  作者：Giulia Stazi、Cecilia Battistelli、Valentina Piano、Roberta Mazzone、Biagina Marrocco、Sara Marchese、Sharon M. Louie、Clemens Zwergel、Lorenzo Antonini、Alexandros Patsilinakos、Rino Ragno、Monica Viviano、Gianluca Sbardella、Alessia Ciogli、Giancarlo Fabrizi、Roberto Cirilli、Raffaele Strippoli、Alessandra Marchetti、Marco Tripodi、Daniel K. Nomura、Andrea Mattevi、Antonello Mai、Sergio Valente

  DOI：10.1016/j.ejmech.2018.11.050

  日期：2019.2

  In aggressive tumors, alkylglyceronephosphate synthase (AGPS) controls cellular ether phospholipid utilization and metabolism to promote cancer cell proliferation and motility. SAR studies on the first-in-class AGPS inhibitor 1, discovered by our group, led to the 2,6-difluoro analog 2i which showed higher binding affinity than 1 in vitro. In 231MFP cancer cells, 2i reduced ether lipids levels and cell migration rate. When tested in PC-3 and MDA-MB-231 cancer cells, 2i specifically impaired epithelial to mesenchymal transition (EMT) by modulating E-cadherin, Snail and MMP2 expression levels. Moreover, the combination of siRNAs against AGPS and 2i provided no additive effect, confirming that the modulation of 2i on EMT specifically relies on AGPS inhibition. Finally, this compound also affected cancer cell proliferation especially in MDA-MB-231 cells expressing higher AGPS level, whereas it provided negligible effects on MeT5A, a non-tumorigenic cell line, thus showing cancer specificity. (C) 2018 Elsevier Masson SAS. All rights reserved.