N-(1-benzylpiperidin-4-ylmethyl)-N-pentylamine | 920463-20-3

• 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: N-(1-benzylpiperidin-4-ylmethyl)-N-pentylamine
• 英文别名: N-[(1-benzylpiperidin-4-yl)methyl]pentan-1-amine
• CAS: 920463-20-3
• 化学式: C₁₈H₃₀N₂
• 分子量: 274.45
• InChiKey: WUQVBJLYXJCPBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1-benzylpiperidin-4-ylmethyl)-N-pentylamine 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 N-(piperidin-4-ylmethyl)pentan-1-amine
  参考文献：
  名称：

  [35S]GTPγS binding studies of amphiphilic drugs-activated Gi proteins: A caveat

  摘要：

  This paper documents a serious problem met during the testing of Gi protein-activating properties of a new series of synthetic compounds by measuring the induced binding of [(35)S]GTP gamma S to different subtypes of Gi protein. The problem arose from the strong affinity between [(35)S]GTP gamma S and the tested compounds, that are characterized by several (2-4) positive charges and high lipophilicity. Apparently, such affinity yields insoluble, labelled complexes that, also in the absence of Gi protein, are retained on the filters and give rise to false positive results. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.097
• 作为产物：
  描述：

  4-氨甲基哌啶 在 sodium tetrahydroborate 、 potassium carbonate 、 sodium sulfate 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 10.0h， 生成 N-(1-benzylpiperidin-4-ylmethyl)-N-pentylamine
  参考文献：
  名称：

  新的基于哌啶的衍生物作为sigma受体配体。合成与药理评价

  摘要：

  长期以来，人们一直认为sigma受体（σR）家族是神秘的。实际上，σ2R亚型直到最近才被克隆，揭示了其与TMEM97的同一性，TMEM97是一种NPC1结合蛋白，参与胆固醇的生物合成，并与癌症和神经系统疾病的发病机理有关。为了开发具有σR亲和力的新化学实体，我们在此报告了对σ1和σ2R亚型具有混合亲和力的新哌啶基烷基乙酰胺衍生物的设计和合成。

  DOI：

  10.1016/j.bmcl.2018.08.016

文献信息

• [35S]GTPγS binding studies of amphiphilic drugs-activated Gi proteins: A caveat
  作者：Dina Manetti、Lorenzo Di Cesare Mannelli、Silvia Dei、Luca Guandalini、Elisabetta Martini、Martina Banchelli、Carla Ghelardini

  DOI：10.1016/j.bmcl.2009.02.097

  日期：2009.4

  This paper documents a serious problem met during the testing of Gi protein-activating properties of a new series of synthetic compounds by measuring the induced binding of [(35)S]GTP gamma S to different subtypes of Gi protein. The problem arose from the strong affinity between [(35)S]GTP gamma S and the tested compounds, that are characterized by several (2-4) positive charges and high lipophilicity. Apparently, such affinity yields insoluble, labelled complexes that, also in the absence of Gi protein, are retained on the filters and give rise to false positive results. (c) 2009 Elsevier Ltd. All rights reserved.
• New piperidine-based derivatives as sigma receptor ligands. Synthesis and pharmacological evaluation
  作者：Daniele Zampieri、Maurizio Romano、Renzo Menegazzi、Maria Grazia Mamolo

  DOI：10.1016/j.bmcl.2018.08.016

  日期：2018.10

  involved in cholesterol biosynthesis and implicated in the pathogenesis of cancer and neurologic disorders. With the aim of developing new chemical entities gifted with σR affinity, herein we report the design and synthesis of new piperidine-based alkylacetamide derivatives with mixed affinity towards both σ1 and σ2R subtypes.

  长期以来，人们一直认为sigma受体（σR）家族是神秘的。实际上，σ2R亚型直到最近才被克隆，揭示了其与TMEM97的同一性，TMEM97是一种NPC1结合蛋白，参与胆固醇的生物合成，并与癌症和神经系统疾病的发病机理有关。为了开发具有σR亲和力的新化学实体，我们在此报告了对σ1和σ2R亚型具有混合亲和力的新哌啶基烷基乙酰胺衍生物的设计和合成。