2-(1-benzylpiperidin-4-ylamino)nicotinic acid | 1421000-06-7

• 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)nicotinic acid
• 英文别名: 2-(1-Benzylpiperidin-4-ylamino)nicotinic acid；2-[(1-benzylpiperidin-4-yl)amino]pyridine-3-carboxylic acid
• CAS: 1421000-06-7
• 化学式: C₁₈H₂₁N₃O₂
• 分子量: 311.384
• InChiKey: YPLHKSQHGXSTKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  65.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(1-benzylpiperidin-4-ylamino)nicotinic acid 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 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：

  4-氨基-1-苄基哌啶 在 potassium carbonate 、 potassium hydroxide 作用下， 以 邻二甲苯 、 异丙醇 为溶剂， 反应 16.0h， 生成 2-(1-benzylpiperidin-4-ylamino)nicotinic acid
  参考文献：
  名称：

  US2014/256711

  摘要：

  公开号：

文献信息

• Compound having angiogenesis inhibitory activity, method for preparing same, and pharmaceutical composition comprising same
  申请人：Kim Ji Han

  公开号：US09227955B2

  公开（公告）日：2016-01-05

  Disclosed are an anti-angiogenic compound, represented by Chemical Formula I, or a pharmaceutically acceptable salt thereof, a preparation method thereof, and a pharmaceutically acceptable composition including the same. Because the compound of Chemical Formula I potently suppresses the angiogenesis, the compound of Chemical Formula I is applicable to the prevention and treatment of diseases caused by aberrant activity of vascular endothelial growth factor, and available as an anti-angiogenic agent.

  本发明公开了一种抗血管生成化合物，其化学式为I，或其药学上可接受的盐，以及其制备方法和包括其的药学上可接受的组合物。由于化合物I的强效抑制血管生成作用，化合物I可用于预防和治疗由血管内皮生长因子异常活动引起的疾病，并可作为抗血管生成剂。
• EP2754655
  申请人：——

  公开号：——

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

  公开号：——

  公开（公告）日：——
• US9227955B2
  申请人：——

  公开号：US9227955B2

  公开（公告）日：2016-01-05