(4aR,10bR)-4a-Hydroxy-8-isopropyl-9-methoxy-4,4,10b-trimethyl-1,2,3,4,4a,10b-hexahydro-benzo[c]chromen-6-one | 54868-50-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (4aR,10bR)-4a-Hydroxy-8-isopropyl-9-methoxy-4,4,10b-trimethyl-1,2,3,4,4a,10b-hexahydro-benzo[c]chromen-6-one
• 英文别名: Cupresol；(4aR,10bR)-4a-hydroxy-9-methoxy-4,4,10b-trimethyl-8-propan-2-yl-2,3-dihydro-1H-benzo[c]chromen-6-one
• CAS: 54868-50-7
• 化学式: C₂₀H₂₈O₄
• 分子量: 332.44
• InChiKey: MCRAIDDVIKPKMP-WOJBJXKFSA-N

物化性质

• LogP：
  5.752 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  sugiol methylether 在 potassium tert-butylate 、 氧气 作用下， 以 叔丁醇 为溶剂， 生成 (4aR,10bR)-4a-Hydroxy-8-isopropyl-9-methoxy-4,4,10b-trimethyl-1,2,3,4,4a,10b-hexahydro-benzo[c]chromen-6-one
  参考文献：
  名称：

  Interconversions of some diterpenic constituents of Podocarpus ferrugineus

  摘要：

  DOI：

  10.1021/jo00832a075

文献信息

• Unprecedented Elimination Reactions of Cyclic Aldols: A New Biosynthetic Pathway toward the Taiwaniaquinoid Skeleton
  作者：Juan J. Guardia、Antonio Fernández、José Justicia、Houda Zentar、Ramón Alvarez-Manzaneda、Enrique Alvarez-Manzaneda、Rachid Chahboun

  DOI：10.3390/molecules28041524

  日期：——

  The acid treatment of 6,7-seco-abietane dialdehydes gives, in high yield, the corresponding derivatives with the 4a-methyltetrahydrofluorene skeleton of taiwaniaquinoids. A mechanism involving the elimination of formic acid from the cyclic aldol intermediate is proposed here. This process can be postulated as a new biogenetic pathway from abietane diterpenes to taiwaniaquinoids. Using this novel reaction

  6,7-seco-abietane 二醛的酸处理以高收率得到具有 taiwaniaquinoids 的 4a-甲基四氢芴骨架的相应衍生物。这里提出了一种涉及从环状羟醛中间体中消除甲酸的机制。这个过程可以假设为从松香二萜到台湾醌的新的生物遗传途径。利用这一新反应，首次获得了具有生物活性的天然铜酚和紫杉醇的对映体特异性合成。
• In Vivo Biological Evaluation of a Synthetic Royleanone Derivative as a Promising Fast-Acting Trypanocidal Agent by Inducing Mitochondrial-Dependent Necrosis
  作者：Rubén Martín-Escolano、Juan J. Guardia、Javier Martín-Escolano、Nuria Cirauqui、Antonio Fernández、Maria J. Rosales、Rachid Chahboun、Manuel Sánchez-Moreno、Enrique Alvarez-Manzaneda、Clotilde Marín

  DOI：10.1021/acs.jnatprod.0c00651

  日期：2020.12.24

  The life-long and life-threatening Chagas disease is one of the most neglected tropical diseases caused by the protozoan parasite Trypanosoma cruzi. It is a major public health problem in Latin America, as six to seven million people are infected, being the principal cause of mortality in many endemic regions. Moreover, Chagas disease has become widespread due to migrant populations. Additionally, there are no vaccines nor effective treatments to fight the disease because of its long-term nature and complex pathology. Therefore, these facts emphasize how crucial the international effort for the development of new treatments against Chagas disease is. Here, we present the in vitro and in vivo trypanocidal activity of some oxygenated abietane diterpenoids and related compounds. The 1,4-benzoquinone 15, not yet reported, was identified as a fast-acting trypanocidal drug with efficacy against different strains in vitro and higher activity and lower toxicity than benznidazole in both phases of murine Chagas disease. The mode of action was also evaluated, suggesting that quinone 15 kills T. cruzi by inducing mitochondrion-dependent necrosis through a bioenergetics collapse caused by a mitochondrial membrane depolarization and iron-containing superoxide dismutase inhibition. Therefore, the abietane 1,4-benzoquinone 15 can be considered as a new candidate molecule for the development of an appropriate and commercially accessible anti-Chagas drug.