N-caproylhistamine | 103827-10-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-caproylhistamine
• 英文别名: N-[2-(1H-imidazol-5-yl)ethyl]hexanamide
• CAS: 103827-10-7
• 化学式: C₁₁H₁₉N₃O
• 分子量: 209.291
• InChiKey: POWCEFXIBWGZIW-UHFFFAOYSA-N

物化性质

• 熔点：
  128-129 °C(Solv: ethanol (64-17-5))
• 沸点：
  489.6±28.0 °C(Predicted)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-caproylhistamine 生成 (2-tert-Butoxycarbonylamino-4-hexanoylamino-butyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Altman, Janina; Schuhmann, Elfriede; Karaghiosoff, Konstantin, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1991, vol. 46, # 11, p. 1473 - 1488

  摘要：

  DOI：
• 作为产物：
  描述：

  histamine dichloride 、 2-methylpropoxycarbonyl hexanoate 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-caproylhistamine
  参考文献：
  名称：

  Congener derivatives and conjugates of histamine: synthesis and tissue and receptor selectivity of the derivatives

  摘要：

  A series of 19 congener derivatives and conjugates of histamine was synthesized and tested to determine whether the ligands would alter the conventional histamine activity in various tissues. The derivatives, which contained either branched or unbranched aliphatic groups, aromatic amide groups, or dipeptides, exhibited affinities for histamine type 1 and/or type 2 receptors that were widely different from the progenitor. The p-trifluoromethyl derivative of histamine with an intermediate chain length of four methylenes (compound 13) was the most potent lymphocytes H2 receptor agonist but was inactive on guinea pig myocardium H2 receptors. The deletion of a single methylene chain (compound 12) from this compound resulted in total loss of its H2 activity on lymphocytes and its H1 activity on aorta. Compound 12 became an exclusive H1 agonist on lymphocytes H1 receptors. The dipeptide conjugate (compound 17) and the aliphatic congener derivative (compound 18), both with four methylenes, retained some of the activity on guinea pig myocardium H2 receptors, but lost their activity on lymphocytes H2 receptors. Therefore, histamine can be modified at sites that are at a distance from the imidazole moiety, resulting in tissue selective histamine receptor agonists.

  DOI：

  10.1021/jm00394a031

文献信息

• Detection of Novel Cytotoxic Imidazole Alkaloids in Tomato Products by LC-MS/MS
  作者：Yannick Hövelmann、Maria Hahn、Florian Hübner、Hans-Ulrich Humpf

  DOI：10.1021/acs.jafc.9b00461

  日期：2019.4.3

  Imidazole alkaloids represent a rather small group of alkaloids and are assumed not to be of significance to the human food chain so far. In this study, novel imidazole alkaloids occurring in tomato products were synthesized and structurally characterized by nuclear-magnetic-resonance spectroscopy and high-resolution mass spectrometry. These alkaloids are amides of either histidinol or histamine and

  咪唑生物碱仅代表一小部分生物碱，到目前为止，对人类食物链没有重要意义。在这项研究中，合成了西红柿产品中出现的新型咪唑生物碱，并通过核磁共振光谱和高分辨率质谱对其结构进行了表征。这些生物碱是组氨醇或组胺和短链脂肪酸的酰胺，可使用新开发和验证的基于LC-MS / MS的方法在所有28种分析过的番茄产品中进行定量。所分析的番茄产品中的含量范围从大约5μg/ kg到几乎3 mg / kg，以及N辛酸-癸基组织醇及其推定的异构体的含量最高。因此，这些咪唑生物碱作为人类饮食的一部分被规律地摄入。在评估其对HT-29细胞活力的影响过程中，所有化合物均显示从100μM浓度开始显着降低细胞活力。
• KHAN, M. M.;MELMON, K. L.;MARR-LEISY, D.;VERLANDER, M. S.;EGLI, M.;LOK, S+, J. MED. CHEM., 30,(1987) N 11, 2115-2120
  作者：KHAN, M. M.、MELMON, K. L.、MARR-LEISY, D.、VERLANDER, M. S.、EGLI, M.、LOK, S+

  DOI：——

  日期：——