Methyl octadecanimidate;hydrochloride | 35378-90-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: Methyl octadecanimidate;hydrochloride
• CAS: 35378-90-6
• 化学式: C₁₉H₃₉NO*ClH
• 分子量: 333.986
• InChiKey: ULTUSAVGBNDAOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.29
• 重原子数：
  22
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  33.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Methyl octadecanimidate;hydrochloride 在 水 、 sodium ethanolate 、 三乙胺 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 (Z)-3-Amino-icos-2-enoic acid ethyl ester
  参考文献：
  名称：

  Imidate Chemistry: A General and Versatile Synthesis of β-Enaminoesters, β-Ketoesters, and Methyl Ketones from Nitriles

  摘要：

  DOI：

  10.1055/s-1981-29361
• 作为产物：
  描述：

  十八烷腈 、 甲醇 、 盐酸 生成 Methyl octadecanimidate;hydrochloride
  参考文献：
  名称：

  CELERIER J.-P.; DELOISY E.; KAPRON P.; LHOMMET G.; MAITTE P., SYNTHESIS, 1981, NO 2, 130-133

  摘要：

  DOI：

文献信息

• 2-Alkyl-substituted histamines and hydroxyethylimidazoles with G-protein-stimulatory activity
  作者：H Detert、C Leschke、W Tögel、R Seifert、W Schunacki

  DOI：10.1016/0223-5234(96)89166-5

  日期：1996.1

  Cationic-amphiphilic 2-substituted histamines activate pertussis toxin-sensitive guanine nucleotide-binding proteins (G-proteins) by a receptor-independent mechanism. From our recent studies it became apparent that lipophilicity is an important determinant for this G-protein activation, but the influence of basicity remained unknown. We prepared seven novel 2-alkyl-substituted histamines and five novel 2-alkyl-substituted hydroxyethylimidazoles and studied their effects on high-affinity guanosine triphosphate (GTP) hydrolysis in membranes of the human leukemia cell line, HL-60. 2-Octylhistamine was found to be the most effective GTPase activator among 2-substituted histamines presently available (150% stimulation above basal), and 2-tetradecylhistamine is the most potent substance in this regard (pEC(50) = 5.9). Branching of the alkyl chain and the introduction of an ether group adversely affected GTPase activation. Compared to a phenyl ring, a bulky adamantyl sphere enhanced G-protein-stimulatory activity. In the case of 2-(3-bromophenyl)histamine, 2-adamantylhistamine and 2-(3-phenylpropyl)histamine, replacement of the aminoethyl group by a hydroxyethyl group at the imidazole greatly reduced GTPase-activating properties, pointing to the importance of the basic domain in the activation process. Unexpectedly, however, in the case of a very lipophilic substituent (heptadecyl chain) the exchange of the aminoethyl group by a hydroxyethyl group had no substantial inhibitory effect, indicating that the presence of a primary amine is not a conditio sine qua non for a substance being a receptor-independent G-protein activator. Concerning histamine H-1-receptors the newly prepared compounds proved to be weak antagonists.