(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 | 146269-39-8

• 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
• 中文名称: (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
• 英文名称: (E)-Caracasanamide
• 英文别名: Caracasanamide；(E)-3-(3,4-dimethoxyphenyl)-N-[4-[[N'-(3-methylbut-2-enyl)carbamimidoyl]amino]butyl]prop-2-enamide
• CAS: 146269-39-8
• 化学式: C₂₁H₃₂N₄O₃
• 分子量: 388.51
• InChiKey: SZQNZZPMXSFUDT-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  98
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基肉桂酰氯 以 四氢呋喃 、 苯 为溶剂， 生成 (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：

  Crombie, Leslie; Jarrett, Sandra R. M., Journal of the Chemical Society. Perkin transactions I, 1992, # 23, p. 3179 - 3184

  摘要：

  DOI：

文献信息

• Guanidine derivatives having hypotensive activity, composition containing them, and process for obtaining them
  申请人：CONSIGLIO NAZIONALE DELLE RICERCHE

  公开号：EP0330629A2

  公开（公告）日：1989-08-30

  Guanidine derivatives of the following formulas (1) and (2): R¹-NH-(CH₂)NH-NH-R²      (1) wherein: R¹ is hydrogen or optionally substituted cinnamoyl, R² is hydrogen, alkyl or alkenyl, with the proviso that R¹ and R² cannot be both hydrogen, n is an integer from 1 to 8, or: wherein: R³ is truxinoyl or a truxilloyl each optionally substi­tuted, and R² and n are as defined above; pharmaceutical compositions containing such compounds and a process for their extraction and purification from plant material, in particular from Verbesina caracasana.

  下列式子(1)和(2)的胍衍生物： R¹-NH-(CH₂)NH-NH-R² (1) 其中 R¹ 是氢或任选取代的肉桂酰基、 R² 是氢、烷基或烯基，但 R¹ 和 R² 不能都是氢、 n 是 1 至 8 的整数，或 其中 R³ 是 truxinoyl 或 truxilloyl，各自任选被取代，以及 R² 和 n 如上文所定义； 含有此类化合物的药物组合物，以及从植物材料，特别是从 Verbesina caracasana 中提取和纯化此类化合物的工艺。
• 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.
• Crombie, Leslie; Jarrett, Sandra R. M., Journal of the Chemical Society. Perkin transactions I, 1992, # 23, p. 3179 - 3184
  作者：Crombie, Leslie、Jarrett, Sandra R. M.

  DOI：——

  日期：——