1,2-Benzenediol, 4-[2-[(5-amino-1-methylpentyl)amino]-1-hydroxyethyl]-,dihydrochloride | 88719-37-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1,2-Benzenediol, 4-[2-[(5-amino-1-methylpentyl)amino]-1-hydroxyethyl]-,dihydrochloride
• 英文别名: 4-[2-(5-Amino-1-methyl-pentylamino)-1-hydroxy-ethyl]-benzene-1,2-diol; hydrochloride
• CAS: 88719-37-3；95483-76-4；95484-37-0
• 化学式: C₁₄H₂₄N₂O₃*2ClH
• 分子量: 341.278
• InChiKey: ZLAPADDNCDVDNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  98.74
• 氢给体数：
  5.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  6-异氰酸-2-己酮 在 氢溴酸 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 苯 为溶剂， 反应 17.5h， 生成 1,2-Benzenediol, 4-[2-[(5-amino-1-methylpentyl)amino]-1-hydroxyethyl]-,dihydrochloride
  参考文献：
  名称：

  Conjugates of Catecholamines. 5. Synthesis and β-Adrenergic Activity of N-(Aminoalkyl)norepinephrine Derivatives

  摘要：

  A novel series of N-aminoalkyl congeners and model derivatives of norepinephrine has been synthesized. Compounds that were structurally related to epinephrine were prepared from fully protected intermediates. Alternatively, isoproterenol-related compounds were synthesized via reductive amination of preformed methyl ketone derivatives with norepinephrine. The beta-adrenergic activities of these new compounds were assessed through measurement of intracellular cyclic AMP accumulation in S49 mouse lymphoma cells and displacement of iodocyanopindolol (ICYP) from membrane preparations. Congeners that contained an underivatized primary amine function exhibited virtually no activity in these assays. However, when this amine function was acylated (e.g., to an amide, carbamate, urea, sulfonamide, etc.), the products exhibited generally increased beta-adrenergic activity, which was, however, strongly dependent on the nature of the acylating group and also the length of the spacer. In particular, a benzyl carbamate derivative containing a branched, seven-carbon spacer group was 40 times more potent than isoproterenol in the in vitro S49 assay.

  DOI：

  10.1021/jm50001a017