Butyl-carbamic acid 4-[2-(3,4-dihydroxy-phenyl)-2-hydroxy-ethylamino]-pentyl ester | 88719-67-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Butyl-carbamic acid 4-[2-(3,4-dihydroxy-phenyl)-2-hydroxy-ethylamino]-pentyl ester
• 英文别名: 4-[[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]amino]pentyl N-butylcarbamate
• CAS: 88719-67-9
• 化学式: C₁₈H₃₀N₂O₅
• 分子量: 354.447
• InChiKey: NTIKQHXVJFNSPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  111
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  DL-去甲肾上腺素 、 Butyl-carbamic acid 4-oxo-pentyl ester 在 platinum(IV) oxide 氢气 、 溶剂黄146 作用下， 反应 10.0h， 生成 Butyl-carbamic acid 4-[2-(3,4-dihydroxy-phenyl)-2-hydroxy-ethylamino]-pentyl ester
  参考文献：
  名称：

  Conjugates of Catecholamines. 6. Synthesis and β-Adrenergic Activity of N - (Hydroxyalkyl)catecholamine Derivatives

  摘要：

  A new series of catecholamines has been prepared in which the N-alkyl substituent of dl-epinephrine or dl-isoproterenol has been extended by a methylene chain terminated by a hydroxyl group or derived functionality (e.g., carbamate or ester). These functionalized catecholamines (congeners) and model compounds were prepared with the goal of eventual attachment to polymeric carrier molecules. The beta-adrenergic agonist activity of the derivatives was evaluated in vitro by measuring the intracellular accumulation of cyclic AMP in S49 mouse lymphoma cells and by the displacement of iodocyanopindolol (ICYP). A n-butylcarbamate derivative (compound 15) was the most active compound in this series with a potency 190 times greater than dl-isoproterenol in the S49 assay. The biological results indicate that minor modifications in structure in the N-alkyl substituent of the catecholamine can influence the pharmacologic activity.

  DOI：

  10.1021/jm50001a018

文献信息

• Conjugates of Catecholamines. 6. Synthesis and β-Adrenergic Activity of N - (Hydroxyalkyl)catecholamine Derivatives
  作者：Allen B. Reitz、Mitchell A. Avery、Roberto P. Rosenkranz、Michael S. Verlander、Kenneth L. Melmon、Brian B. Hoffman、Yasio Akita、Neal Castagnoli、Murry Goodman

  DOI：10.1021/jm50001a018

  日期：1985.5

  A new series of catecholamines has been prepared in which the N-alkyl substituent of dl-epinephrine or dl-isoproterenol has been extended by a methylene chain terminated by a hydroxyl group or derived functionality (e.g., carbamate or ester). These functionalized catecholamines (congeners) and model compounds were prepared with the goal of eventual attachment to polymeric carrier molecules. The beta-adrenergic agonist activity of the derivatives was evaluated in vitro by measuring the intracellular accumulation of cyclic AMP in S49 mouse lymphoma cells and by the displacement of iodocyanopindolol (ICYP). A n-butylcarbamate derivative (compound 15) was the most active compound in this series with a potency 190 times greater than dl-isoproterenol in the S49 assay. The biological results indicate that minor modifications in structure in the N-alkyl substituent of the catecholamine can influence the pharmacologic activity.