12-(benzyloxy)abieta-8,11,13-trien-18-al | 62691-18-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 12-(benzyloxy)abieta-8,11,13-trien-18-al
• 英文别名: (1R,4aS,10aR)-1,4a-dimethyl-6-phenylmethoxy-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carbaldehyde
• CAS: 62691-18-3
• 化学式: C₂₇H₃₄O₂
• 分子量: 390.566
• InChiKey: SHSKMVWASIWRNY-GMQQYTKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  12-(benzyloxy)abieta-8,11,13-trien-18-al 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氢气 、 一水合肼 作用下， 以 氯仿 、 溶剂黄146 、 二乙二醇 为溶剂， 反应 2.0h， 生成 12-benzoyloxy-11-hydroxyabieta-8,11,13-triene
  参考文献：
  名称：

  Synthesis of Taxodione, Royleanone, Cryptojaponol, and Methyl 11-Hydroxy-12-methoxy-7-oxoabieta-8,11)13-trien-18-oate

  摘要：

  使用过氧化苯甲酰成功地对 12-hydroxyabieta-8,11,13-trien-18-oate (II) 和 ferruginol (XXXII) 进行了 C-11 位置的氧化、生成的苯酚（VII 和 XXXVII）被进一步转化为 taxodione（III）、royleanone（IV）、cryptojaponol（V）和 11-hydroxy-12-methoxy-7-oxoabieta-8,11,13-trien-18-oate （VI）甲基。

  DOI：

  10.1246/bcsj.50.266
• 作为产物：
  描述：

  12-Benzyloxyabieta-8,11,13-trien-18-saeuremethylester 生成 12-(benzyloxy)abieta-8,11,13-trien-18-al
  参考文献：
  名称：

  Synthesis of Taxodione, Royleanone, Cryptojaponol, and Methyl 11-Hydroxy-12-methoxy-7-oxoabieta-8,11)13-trien-18-oate

  摘要：

  使用过氧化苯甲酰成功地对 12-hydroxyabieta-8,11,13-trien-18-oate (II) 和 ferruginol (XXXII) 进行了 C-11 位置的氧化、生成的苯酚（VII 和 XXXVII）被进一步转化为 taxodione（III）、royleanone（IV）、cryptojaponol（V）和 11-hydroxy-12-methoxy-7-oxoabieta-8,11,13-trien-18-oate （VI）甲基。

  DOI：

  10.1246/bcsj.50.266

文献信息

• Synthesis of (+)-Hanagokenol A, (+)-Fortunins E, G, H, and (-)-Sugikurojin A from Abietic Acid
  作者：Enrique Alvarez-Manzaneda、Rachid Chahboun、Esteban Alvarez、Jose Ramos、Juan Guardia、Ibtissam Messouri、Ikram Chayboun、Ahmed Mansour、Abdelaziz Dahdouh

  DOI：10.1055/s-0030-1258226

  日期：2010.10

  A series of 12-hydroxy-substituted abietane diterpenes, functionalized on C19 or C18, have been synthesized starting from 18-hydroxyferruginol. The first synthesis of antibacterial hanagokenol A and fortunins E, G, and H, and a new procedure for preparing sugikurojin A and the immunosuppressive 19-hydroxy­-ferruginol are reported. antibiotics - diastereoselectivity - phenols - terpenoids - oxidation

  从18-羟基铁苦丁醇开始合成了一系列在C19或C18上官能化的12-羟基取代的枞豆二萜。据报道，抗菌素花粉酚A和fortunins E，G和H的首次合成，以及制备sugikurojin A和免疫抑制性19-羟基-铁粉酚的新方法。 抗生素-非对映选择性-酚类-萜类化合物-氧化
• 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.