2-(1-benzylpiperidin-4-ylamino)nicotinonitrile | 918535-88-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-(1-benzylpiperidin-4-ylamino)nicotinonitrile
• 英文别名: 2-[(1-Benzylpiperidin-4-yl)amino]pyridine-3-carbonitrile
• CAS: 918535-88-3
• 化学式: C₁₈H₂₀N₄
• mdl: MFCD09935539
• 分子量: 292.384
• InChiKey: BIWCHTNDZQRMSV-UHFFFAOYSA-N

物化性质

• 沸点：
  470.6±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  52
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-benzylpiperidin-4-ylamino)nicotinonitrile 在 氯化亚砜 、 potassium hydroxide 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 21.0h， 生成 2-(1-benzylpiperidin-4-ylamino)nicotinyl chloride
  参考文献：
  名称：

  Synthesis and evaluation of nicotinamide derivative as anti-angiogenic agents

  摘要：

  Previously, we have found that BRN-103, a nicotinamide derivative, inhibits vascular endothelial growth factor (VEGF)-mediated angiogenesis signaling in human endothelial cells. During our continuous efforts to identify more potent anti-angiogenic agents, we synthesized various nicotinamide derivatives and evaluated their anti-angiogenic effects. We found that 2-{1[1-(6-chloro-5-fluoropyrimidin-4-yl)ethyl]piperidin-4-ylamino}-N-(3-chlorophenyl) pyridine-3-carboxamide (BRN-250) significantly inhibited human umbilical vascular endothelial cells (HUVECs) proliferation, migration, tube formation, and microvessel growth in a concentration range of 10-100 nM. Furthermore, BRN-250 inhibited the VEGF-induced phosphorylation and intracellular tyrosine kinase activity of VEGF receptor 2 (VEGFR2) and the activation of its downstream AKT pathway. Taken together, these findings suggest that BRN-250 be considered a potential lead compound for cancer therapy. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.125
• 作为产物：
  描述：

  2-氯-3-氰基吡啶 、 4-氨基-1-苄基哌啶 在 potassium carbonate 作用下， 以 邻二甲苯 为溶剂， 反应 4.0h， 以71.5%的产率得到2-(1-benzylpiperidin-4-ylamino)nicotinonitrile
  参考文献：
  名称：

  US2014/256711

  摘要：

  公开号：

文献信息

• WO2007/1975
  申请人：——

  公开号：——

  公开（公告）日：——
• EP2754655
  申请人：——

  公开号：——

  公开（公告）日：——
• US20140256711A1
  申请人：——

  公开号：——

  公开（公告）日：——
• Heteroatom-linked substituted piperidines and derivatives thereof useful as histamine H3 antagonists
  申请人：Aslanian G. Robert

  公开号：US20070015807A1

  公开（公告）日：2007-01-18

  Disclosed are novel compounds of the formula or a pharmaceutically acceptable salt thereof, wherein: M 1 and M 3 are CH or N; M 2 is CH, CF or N; Y is —C(═O)—, —C(═S)—, —(CH 2 ) q —, —C(═NOR 7 )— or —SO 1-2 —; Z is a bond or optionally substituted alkylene or alkenylene; R 1 is H, or alkyl, cycloalkyl, aryl, heteroaryl, heterocycloalkyl, all optionally substituted, or a group of the formula: where ring A is a heteroaryl ring; R 2 is optionally substituted alkyl, alkenyl, aryl, heteroaryl, cycloalkyl or heterocycloalkyl; R 3 is H, —C(O)NH 2 , or alkyl, aryl, cycloalkyl, heterocycloalkyl or heteroaryl, all optionally substituted; and the remaining variables are as defined in the specification; compositions and methods of treating allergy-induced airway responses, congestion, obesity, metabolic syndrome, alcoholic fatty liver disease, hepatic steatosis, nonalcoholic steatohepatitis, cirrhosis, hepatacellular carcinoma and cognition deficit disorders using said compounds, alone or in combination with other agents.
• HETEROATOM-LINKED SUBSTITUTED PIPERIDINES AND DERIVATIVES THEREOF USEFUL AS HISTAMINE H3 ANTAGONISTS
  申请人：Aslanian Robert G.

  公开号：US20090286830A1

  公开（公告）日：2009-11-19

  Disclosed are novel compounds of the formula or a pharmaceutically acceptable salt thereof, wherein: M 1 and M 3 are CH or N; M 2 is CH, CF or N; Y is —C(═O)—, —C(═S)—, —(CH 2 ) q —, —C(═NOR 7 )— or —SO 1-2 —; Z is a bond or optionally substituted alkylene or alkenylene; R 1 is H, or alkyl, cycloalkyl, aryl, heteroaryl, heterocycloalkyl, all optionally substituted, or a group of the formula: where ring A is a heteroaryl ring; R 2 is optionally substituted alkyl, alkenyl, aryl, heteroaryl, cycloalkyl or heterocycloalkyl; R 3 is H, —C(O)NH 2 , or alkyl, aryl, cycloalkyl, heterocycloalkyl or heteroaryl, all optionally substituted; and the remaining variables are as defined in the specification; compositions and methods of treating allergy-induced airway responses, congestion, obesity, metabolic syndrome, alcoholic fatty liver disease, hepatic steatosis, nonalcoholic steatohepatitis, cirrhosis, hepatacellular carcinoma and cognition deficit disorders using said compounds, alone or in combination with other agents.