5-Cyclohexyl-2-methyl-pentanoic acid amide | 1379365-22-6

• 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: 5-Cyclohexyl-2-methyl-pentanoic acid amide
• 英文别名: Cyclohexanepentanamide, I+/--methyl-；5-cyclohexyl-2-methylpentanamide
• CAS: 1379365-22-6
• 化学式: C₁₂H₂₃NO
• 分子量: 197.321
• InChiKey: SYKLNPOWYRJPQQ-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  5-Cyclohexyl-2-methyl-pentanoic acid amide 在 phosphorus pentoxide 作用下， 生成 5-Cyclohexyl-2-methyl-pentanenitrile
  参考文献：
  名称：

  2-Substituted histamines with G-protein-stimulatory activity

  摘要：

  The cationic-amphiphilic 2-substituted histamines, 2-(3-chlorophenyl)histamine (2-[2-(3-chlorophenyl)-1H-imidazol-4-yl]ethanamine) and 2-(2-cyclohexylethyl)histamine, activate pertussis toxin-sensitive guanine nucleotide-binding proteins (G-proteins) of the G(i)-subfamily by a receptor-independent mechanism. We studied structure-activity relationships of 2-substituted histamine derivatives for this G-protein activation using six known and 12 newly synthesized compounds. Elongation of the alkyl chain between imidazole and the ring system enhanced the potency and efficiency of substances in activating high-affinity GTP hydrolysis, ie the enzymatic activity of G-protein alpha-subunits, in membranes of HL-60 leukemic cells. Cyclopentyl-, cyclohexyl- and norbornyl-substituted histamines were more effective and potent than phenyl-substituted histamines in mediating G-protein activation in HL-60 membranes and in activating reconstituted bovine brain G(i)/G(o)-proteins. Our data show that the chain length and the type of ring system are important determinants for receptor-independent G-protein activation by 2-substituted histamines. With respect to histamine H-1-receptors, most of the substances studied displayed weak antagonistic activity.

  DOI：

  10.1016/0223-5234(96)88235-3
• 作为产物：
  描述：

  5-Cyclohexyl-2-methyl-pentanoyl chloride 在 ammonium hydroxide 作用下， 生成 5-Cyclohexyl-2-methyl-pentanoic acid amide
  参考文献：
  名称：

  2-Substituted histamines with G-protein-stimulatory activity

  摘要：

  The cationic-amphiphilic 2-substituted histamines, 2-(3-chlorophenyl)histamine (2-[2-(3-chlorophenyl)-1H-imidazol-4-yl]ethanamine) and 2-(2-cyclohexylethyl)histamine, activate pertussis toxin-sensitive guanine nucleotide-binding proteins (G-proteins) of the G(i)-subfamily by a receptor-independent mechanism. We studied structure-activity relationships of 2-substituted histamine derivatives for this G-protein activation using six known and 12 newly synthesized compounds. Elongation of the alkyl chain between imidazole and the ring system enhanced the potency and efficiency of substances in activating high-affinity GTP hydrolysis, ie the enzymatic activity of G-protein alpha-subunits, in membranes of HL-60 leukemic cells. Cyclopentyl-, cyclohexyl- and norbornyl-substituted histamines were more effective and potent than phenyl-substituted histamines in mediating G-protein activation in HL-60 membranes and in activating reconstituted bovine brain G(i)/G(o)-proteins. Our data show that the chain length and the type of ring system are important determinants for receptor-independent G-protein activation by 2-substituted histamines. With respect to histamine H-1-receptors, most of the substances studied displayed weak antagonistic activity.

  DOI：

  10.1016/0223-5234(96)88235-3