4-[[2-(3,4-Dihydroxyphenyl)-2-hydroxyethyl]amino]pentyl 4-methylbenzoate | 95483-05-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[[2-(3,4-Dihydroxyphenyl)-2-hydroxyethyl]amino]pentyl 4-methylbenzoate
• CAS: 95483-05-9；95483-36-6
• 化学式: C₂₁H₂₇NO₅
• 分子量: 373.449
• InChiKey: NSVXVUGAGGSSJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  99
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-羟基-2-戊酮 在 platinum(IV) oxide 吡啶 、 氢气 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 23.0 ℃ 、101.33 kPa 条件下， 反应 10.5h， 生成 4-[[2-(3,4-Dihydroxyphenyl)-2-hydroxyethyl]amino]pentyl 4-methylbenzoate
  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.