dl-7-O-Benzyl-4'-O-methyl-coclaurin | 50300-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: dl-7-O-Benzyl-4'-O-methyl-coclaurin
• 英文别名: 7-benzyloxy-6-methoxy-1-(4-methoxy-benzyl)-1,2,3,4-tetrahydro-isoquinoline；7-Benzyloxy-6-methoxy-1-(4-methoxy-benzyl)-1,2,3,4-tetrahydro-isochinolin；7-O-benzyl-12-O-methylcoclaurine；6-methoxy-1-[(4-methoxyphenyl)methyl]-7-phenylmethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS: 50300-13-5
• 化学式: C₂₅H₂₇NO₃
• 分子量: 389.494
• InChiKey: CMIGKYDKJFFFHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(4-methoxybenzyl)-7-benzyloxy-6-methoxy-3,4-dihydroisoquinoline 在 sodium tetrahydroborate 作用下， 以75%的产率得到dl-7-O-Benzyl-4'-O-methyl-coclaurin
  参考文献：
  名称：

  Simplified Tetrandrine Congeners as Possible Antihypertensive Agents with a Dual Mechanism of Action

  摘要：

  A series of O- and/or N-substituted derivatives of (+/-)-coclaurine (1a) were synthesized as simplified structural mimics of the antihypertensive alkaloid tetrandrine (2) and assayed for binding to brain cortical sites labeled with the alpha(1)-adrenergic radioligand [H-3]prazosin or the calcium channel radioligand [H-3]-diltiazem. The introduction of O-benzyl groups on the coclaurine molecule, which exhibits only adrenergic antagonist activity, led to the appearance of calcium channel blocking activity comparable to that of tetrandrine while retaining adrenolytic activity in the same concentration range. Contraction of aortal rings with noradrenaline or KCl was relaxed more potently by some of these coclaurine derivatives than by tetrandrine, suggesting leads for the development of novel antihypertensive drugs with a dual mechanism of action.

  DOI：

  10.1021/np030022+

文献信息

• Tomita et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1950, vol. 70, p. 152
  作者：Tomita et al.

  DOI：——

  日期：——
• Simplified Tetrandrine Congeners as Possible Antihypertensive Agents with a Dual Mechanism of Action
  作者：Patricio Iturriaga-Vásquez、Raquel Miquel、M. Dolores Ivorra、M. Pilar D'Ocon、Bruce K. Cassels

  DOI：10.1021/np030022+

  日期：2003.7.1

  A series of O- and/or N-substituted derivatives of (+/-)-coclaurine (1a) were synthesized as simplified structural mimics of the antihypertensive alkaloid tetrandrine (2) and assayed for binding to brain cortical sites labeled with the alpha(1)-adrenergic radioligand [H-3]prazosin or the calcium channel radioligand [H-3]-diltiazem. The introduction of O-benzyl groups on the coclaurine molecule, which exhibits only adrenergic antagonist activity, led to the appearance of calcium channel blocking activity comparable to that of tetrandrine while retaining adrenolytic activity in the same concentration range. Contraction of aortal rings with noradrenaline or KCl was relaxed more potently by some of these coclaurine derivatives than by tetrandrine, suggesting leads for the development of novel antihypertensive drugs with a dual mechanism of action.