N-(2-chlorohomoveratryl)propanamide | 99318-58-8

• 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: N-(2-chlorohomoveratryl)propanamide
• 英文别名: N-(2-chloro-3,4-dimethoxyphenethyl)propionamide；N-[2-(2-chloro-3,4-dimethoxyphenyl)ethyl]propanamide
• CAS: 99318-58-8
• 化学式: C₁₃H₁₈ClNO₃
• 分子量: 271.744
• InChiKey: WVUDASJWTRHHTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-chlorohomoveratryl)propanamide 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以79%的产率得到N-(n-propyl)-2-(2-chloro-3,4-dimethoxyphenyl)ethylamine
  参考文献：
  名称：

  Synthesis and renal vasodilator activity of 2-chlorodopamine and N-substituted derivatives

  摘要：

  A four-step synthesis of 2-chlorodopamine (2b) is presented as well as methods for the syntheses of the N-methyl, ethyl, and n-propyl analogues (2c-e). Compounds 2b and 2c were essentially equipotent to dopamine for increasing renal blood flow in anesthetized dogs that had been treated with the alpha-adrenergic antagonist phenoxybenzamine. The increases in renal blood flow were blocked by the DA1 antagonist (R)-(+)-8-chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepine. Compounds 2d and 2e were significantly less potent than dopamine in the same model; the increases in renal blood flow were attenuated by propranolol and blocked by a combination of propranolol and (R)-(+)-8-chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepine. The significance of an o-chloro substituent on dopamine analogues for the activation of the DA1 receptor is briefly discussed.

  DOI：

  10.1021/jm00159a005
• 作为产物：
  描述：

  2-氯-1-(氯甲基)-3,4-二甲氧基苯 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 18-冠醚-6 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 171.0h， 生成 N-(2-chlorohomoveratryl)propanamide
  参考文献：
  名称：

  Synthesis and renal vasodilator activity of 2-chlorodopamine and N-substituted derivatives

  摘要：

  A four-step synthesis of 2-chlorodopamine (2b) is presented as well as methods for the syntheses of the N-methyl, ethyl, and n-propyl analogues (2c-e). Compounds 2b and 2c were essentially equipotent to dopamine for increasing renal blood flow in anesthetized dogs that had been treated with the alpha-adrenergic antagonist phenoxybenzamine. The increases in renal blood flow were blocked by the DA1 antagonist (R)-(+)-8-chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepine. Compounds 2d and 2e were significantly less potent than dopamine in the same model; the increases in renal blood flow were attenuated by propranolol and blocked by a combination of propranolol and (R)-(+)-8-chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepine. The significance of an o-chloro substituent on dopamine analogues for the activation of the DA1 receptor is briefly discussed.

  DOI：

  10.1021/jm00159a005

文献信息

• N,N-Di-(n-Propyl)dopamine derivatives
  申请人：SmithKline Beckman Corporation

  公开号：US04529604A1

  公开（公告）日：1985-07-16

  N,N-Di-(n-propyl)dopamine derivatives having peripheral dopamine receptor agonist activity prepared by synthetic routes known for phenethylamines. The renal vasodilator effect of 3,4-dihydroxy-N,N-di(n-propyl)-phenethylamine is potentiated by the concomitant administration of the .beta.-blocker propranolol.

  N,N-二(正丙基)多巴胺衍生物具有外周多巴胺受体激动剂活性，通过已知的苯乙胺合成途径制备。3,4-二羟基-N,N-二(正丙基)-苯乙胺的肾血管扩张作用通过同时给予β受体阻滞剂普萘洛尔而增强。
• MCCARTHY J. R.; MCCOWAN J.; ZIMMERMAN M. B.; WENGER M. A.; EMMERT L. W., J. MED. CHEM., 29,(1986) N 9, 1586-1590
  作者：MCCARTHY J. R.、 MCCOWAN J.、 ZIMMERMAN M. B.、 WENGER M. A.、 EMMERT L. W.

  DOI：——

  日期：——
• US4529604A
  申请人：——

  公开号：US4529604A

  公开（公告）日：1985-07-16
• Synthesis and renal vasodilator activity of 2-chlorodopamine and N-substituted derivatives
  作者：James R. McCarthy、Jefferson McCowan、Mark B. Zimmerman、Marcia A. Wenger、Lee W. Emmert

  DOI：10.1021/jm00159a005

  日期：1986.9

  A four-step synthesis of 2-chlorodopamine (2b) is presented as well as methods for the syntheses of the N-methyl, ethyl, and n-propyl analogues (2c-e). Compounds 2b and 2c were essentially equipotent to dopamine for increasing renal blood flow in anesthetized dogs that had been treated with the alpha-adrenergic antagonist phenoxybenzamine. The increases in renal blood flow were blocked by the DA1 antagonist (R)-(+)-8-chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepine. Compounds 2d and 2e were significantly less potent than dopamine in the same model; the increases in renal blood flow were attenuated by propranolol and blocked by a combination of propranolol and (R)-(+)-8-chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepine. The significance of an o-chloro substituent on dopamine analogues for the activation of the DA1 receptor is briefly discussed.