(E)-4-2,N³-bis(tert-butoxycarbonyl)-N³-(γ,γ-dimethylallyl)guanidino>-1-<(3,4-dimethoxycinnamoyl)amino>butane | 150785-46-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-4-2,N³-bis(tert-butoxycarbonyl)-N³-(γ,γ-dimethylallyl)guanidino>-1-<(3,4-dimethoxycinnamoyl)amino>butane
• 英文别名: (E)-4-[N²,N³-bis(tert-butoxycarbonyl)-N³-(γ,γ-dimethylallyl)guanidino]-1-[(3,4-dimethoxycinnamoyl)amino]butane；tert-butyl N-[N'-[4-[[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]amino]butyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-N-(3-methylbut-2-enyl)carbamate
• CAS: 150785-46-9
• 化学式: C₃₁H₄₈N₄O₇
• 分子量: 588.745
• InChiKey: PKBOWXKOWODFFW-JQIJEIRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  42
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-4-2,N³-bis(tert-butoxycarbonyl)-N³-(γ,γ-dimethylallyl)guanidino>-1-<(3,4-dimethoxycinnamoyl)amino>butane 在 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以60%的产率得到(E)-3-(3,4-二甲氧基苯基)-N-[4-[(N'-(3-甲基丁-2-烯基)甲脒基)氨基]丁基]丙-2-烯酰胺
  参考文献：
  名称：

  Novel hypotensive agents from Verbesina caracasana. 2. Synthesis and pharmacology of caracasanamide

  摘要：

  Caracasanamide, one of the hypotensive agents isolated from Verbesina caracasana, is a mixture of (Z)-1a and (E)-lb forms of 1-[(3,4-dimethoxycinnamoyl)amino]-4-[(3-methyl-2-butenyl)-guanidino]butane.1 The structure of (E)-caracasanamide (1b) was confirmed by high-yielding synthesis starting from N,N'-bis(tert-butoxycarbonyl)-S-methylisothiourea. The water-soluble Z-form of 1a, assayed by iv route in anesthetized rats at doses ranging from 50 to 1600 mug/kg body weight, was found to decrease blood pressure, to increase cardiac inotropism, respiratory frequency, and tidal volume, and to induce a very slight and not significant tachycardia. Higher doses determined respiratory depression and, in some cases, consequent cardiac arrest. The compound was shown to affect cardiovascular function by acting at the vascular level in inducing arterial vasodilation, by determining sympathetic hypotone through central neurogenic mechanisms, and by interacting with the cardiac beta1-adrenoreceptors. The respiratory effects were independent of the cardiovascular ones. In lowering blood pressure, the compound was more potent than guanethidine and not less potent than reserpine and papaverine. (Z)-Caracasanamide may therefore be useful in the treatment of arterial hypertension of moderate degree.

  DOI：

  10.1021/jm00072a016
• 作为产物：
  描述：

  N,N'-bis(tert-butoxycarbonyl)-N-(γ,γ-dimethylallyl)-S-methylisothiourea 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 (E)-4-2,N³-bis(tert-butoxycarbonyl)-N³-(γ,γ-dimethylallyl)guanidino>-1-<(3,4-dimethoxycinnamoyl)amino>butane
  参考文献：
  名称：

  Novel hypotensive agents from Verbesina caracasana. 2. Synthesis and pharmacology of caracasanamide

  摘要：

  Caracasanamide, one of the hypotensive agents isolated from Verbesina caracasana, is a mixture of (Z)-1a and (E)-lb forms of 1-[(3,4-dimethoxycinnamoyl)amino]-4-[(3-methyl-2-butenyl)-guanidino]butane.1 The structure of (E)-caracasanamide (1b) was confirmed by high-yielding synthesis starting from N,N'-bis(tert-butoxycarbonyl)-S-methylisothiourea. The water-soluble Z-form of 1a, assayed by iv route in anesthetized rats at doses ranging from 50 to 1600 mug/kg body weight, was found to decrease blood pressure, to increase cardiac inotropism, respiratory frequency, and tidal volume, and to induce a very slight and not significant tachycardia. Higher doses determined respiratory depression and, in some cases, consequent cardiac arrest. The compound was shown to affect cardiovascular function by acting at the vascular level in inducing arterial vasodilation, by determining sympathetic hypotone through central neurogenic mechanisms, and by interacting with the cardiac beta1-adrenoreceptors. The respiratory effects were independent of the cardiovascular ones. In lowering blood pressure, the compound was more potent than guanethidine and not less potent than reserpine and papaverine. (Z)-Caracasanamide may therefore be useful in the treatment of arterial hypertension of moderate degree.

  DOI：

  10.1021/jm00072a016

文献信息

• Novel hypotensive agents from Verbesina caracasana. 2. Synthesis and pharmacology of caracasanamide
  作者：Giuliano Delle Monache、Bruno Botta、Franco Delle Monache、Romulo Espinal、Stella C. De Bonnevaux、Carlo De Luca、Maurizio Botta、Federico Corelli、Marco Carmignani

  DOI：10.1021/jm00072a016

  日期：1993.10

  Caracasanamide, one of the hypotensive agents isolated from Verbesina caracasana, is a mixture of (Z)-1a and (E)-lb forms of 1-[(3,4-dimethoxycinnamoyl)amino]-4-[(3-methyl-2-butenyl)-guanidino]butane.1 The structure of (E)-caracasanamide (1b) was confirmed by high-yielding synthesis starting from N,N'-bis(tert-butoxycarbonyl)-S-methylisothiourea. The water-soluble Z-form of 1a, assayed by iv route in anesthetized rats at doses ranging from 50 to 1600 mug/kg body weight, was found to decrease blood pressure, to increase cardiac inotropism, respiratory frequency, and tidal volume, and to induce a very slight and not significant tachycardia. Higher doses determined respiratory depression and, in some cases, consequent cardiac arrest. The compound was shown to affect cardiovascular function by acting at the vascular level in inducing arterial vasodilation, by determining sympathetic hypotone through central neurogenic mechanisms, and by interacting with the cardiac beta1-adrenoreceptors. The respiratory effects were independent of the cardiovascular ones. In lowering blood pressure, the compound was more potent than guanethidine and not less potent than reserpine and papaverine. (Z)-Caracasanamide may therefore be useful in the treatment of arterial hypertension of moderate degree.