methyl 14-hydroxyabieta-8,11,13-trien-18-oate | 57475-59-9

• 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: methyl 14-hydroxyabieta-8,11,13-trien-18-oate
• 英文别名: methyl (1R,4aS,10aR)-8-hydroxy-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate
• CAS: 57475-59-9
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: YDAATSHQUAMAPZ-DUXKGJEZSA-N

物化性质

• 沸点：
  421.6±45.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 14-hydroxyabieta-8,11,13-trien-18-oate 在 ruthenium trichloride 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 双氧水 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 26.0h， 生成 methyl 11,14-diacetoxyabieta-8,11,13-trien-18-oate
  参考文献：
  名称：

  由脱氢松香酸合成12-脱氧丙醛酮，隐醌，11,14-二羟基-8,11,13-松香三烯酮-7-及其相关衍生物

  摘要：

  天然存在的Abetanee醌和对苯二酚，即12-脱氧丙二酮（1a），隐醌（4a）和11,14-dihydroxyabieta- 8,11,13 -trien -7-one（5a）以及色氨酸醌D的差向异构体（2）和F（3）首先由脱氢松香酸（6）合成。

  DOI：

  10.1016/j.tetlet.2005.03.170
• 作为产物：
  描述：

  methyl 13β-hydroxy-14-oxoabieta-7-en-18-oate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以91%的产率得到methyl 14-hydroxyabieta-8,11,13-trien-18-oate
  参考文献：
  名称：

  向14-羟基枞烷二萜的区域选择性途径。由（+）-松香酸正式合成免疫抑制剂（-）-雷公藤甲素

  摘要：

  已经开发出两种方法，以将氧化官能团引入具有完全的区域选择性的abinetanee二萜的C-14中。利用这些，从（+）-松香油中合成抗衰老醌（-）-12-脱氧基丙酮（1）以及抗肿瘤和免疫抑制剂（-）-雷公藤酮（-7）和（-）-雷公藤甲素（8）的形式合成。已经进行了酸（13）。

  DOI：

  10.1016/j.tet.2007.07.088

文献信息

• Regioselective routes towards 14-hydroxyabietane diterpenes. A formal synthesis of immunosuppressant (−)-triptolide from (+)-abietic acid
  作者：Enrique Alvarez-Manzaneda、Rachid Chahboun、Faouzia Bentaleb、Esteban Alvarez、M. Angeles Escobar、Said Sad-Diki、Maria José Cano、Ibtissam Messouri

  DOI：10.1016/j.tet.2007.07.088

  日期：2007.11

  Two procedures to introduce an oxygenated function into the C-14 of abietane diterpenes with complete regioselectivity have been developed. Utilizing these, the synthesis of the antileishmanial quinone (−)-12-deoxyroyleanone (1) and a formal synthesis of antitumour and immunosuppressant (−)-triptonide (7) and (−)-triptolide (8) from (+)-abietic acid (13) have been carried out.

  已经开发出两种方法，以将氧化官能团引入具有完全的区域选择性的abinetanee二萜的C-14中。利用这些，从（+）-松香油中合成抗衰老醌（-）-12-脱氧基丙酮（1）以及抗肿瘤和免疫抑制剂（-）-雷公藤酮（-7）和（-）-雷公藤甲素（8）的形式合成。已经进行了酸（13）。
• Efficient synthesis of the key intermediate triptophenolide methyl ether for the synthesis of (−)-triptolide
  作者：Bing Zhou、Xiaomei Li、Huijin Feng、Yuanchao Li

  DOI：10.1016/j.tet.2010.05.035

  日期：2010.7

  An efficient synthesis of triptophenolide methyl ether 4 from the readily available abietic acid 3 in nine steps is described and successfully applied to the synthesis of (−)-triptolide 1. The route is of characteristic of low cost, high yield and easy operation. In addition, every reaction in this route has been successfully scaled-up to a 100 g substrate level without loss of yield.

  从九个步骤中容易获得的松香酸3高效合成了雷公藤多酚甲醚4，并已成功应用于（-）-雷公藤内酯1的合成。该路线具有成本低，产量高，易于操作的特点。此外，此路线中的每个反应均已成功扩大规模至100 g底物水平，而没有损失收率。
• Collins Oxidation of Methyl (+)-13β-Abiet-8-en-18-oate and Absolute Configuration of Suaveolic Acid
  作者：Takashi Matsumoto、Sachihiko Imai、Shuhei Yuki、Arata Katayama、Manabu Furutani

  DOI：10.1246/bcsj.55.527

  日期：1982.2

  (15) (4%), and methyl (+)-7-oxo-13β-abiet-8-en-18-oate (23%) respectively. It is noteworthy that oxygenation occurs not only at the C-7 and C-11 positions but also at the C-14 position. The oxygenated products obtained in this studies could be useful intermediates for the synthesis of the oxidized diterpenoids of abietane skeleton. To exemplify this, 15 was converted to methyl suaveolate an...

  用柯林斯试剂氧化甲基 (+)-13β-abiet-8-en-18-oate 产生了九种氧化产物。根据光谱和化学数据阐明了它们的结构是甲基 (-)-14-羟基-7-oxoabieta-8,11,13-trien-18-oate (1% 产率), 甲基 (-)-11 ,14-dioxoabieta-8,12-dien-18-oate (1%),methyl (+)-11-oxo-13β-abiet-8-en-18-oate (18%),methyl (-)-8α ,9α-epoxy-7-oxo-13β-abietan-18-oate (2%),methyl (+)-7-oxoabieta-8,11,13-trien-18-oate (2%),methyl (+) -11,14-dihydroxy-7-oxoabieta-8,11,13-trien-18-oate (2%),methyl (+)-7
• Antiviral Profiling of C-18- or C-19-Functionalized Semisynthetic Abietane Diterpenoids
  作者：Miguel A. González-Cardenete、Damir Hamulić、Francisco J. Miquel-Leal、Natalia González-Zapata、Orlando J. Jimenez-Jarava、Yaneth M. Brand、Laura C. Restrepo-Mendez、Marlen Martinez-Gutierrez、Liliana A. Betancur-Galvis、Maria L. Marín

  DOI：10.1021/acs.jnatprod.2c00464

  日期：2022.8.26

  antiviral activities. In this study, a biological evaluation of a number of either C-18- or C-19-functionalized known semisynthetic abietanes against Zika virus, Dengue virus, Herpes virus simplextype 1, and Chikungunya virus are reported. Semisynthetic abietane ferruginol and its analogue 18-(phthalimid-2-yl)ferruginol displayed broad-spectrum antiviral properties. The scale-up synthesis of this analogue

  病毒感染每年影响数百万患者。尽管已知有数百种病毒具有致病性，但只有少数可以在临床上使用可用的抗病毒药物进行治疗。基于自然的药物疗法可能是治疗病毒性疾病的合适替代方案。几种天然和半合成的松香型二萜已显示出重要的抗病毒活性。在这项研究中，针对寨卡病毒、登革热病毒、单纯疱疹病毒1型和基孔肯雅病毒的许多 C-18 或 C-19 功能化的已知半合成松香的生物学评估被报道。半合成枞树烷 ferruginol 及其类似物 18-(phthalimid-2-yl)ferruginol 显示出广谱抗病毒特性。该类似物的放大合成已针对进一步研究和开发进行了优化。该分子对哥伦比亚寨卡病毒株的 EC 50介于 5.0 和 10.0 μM 之间，对基孔肯雅病毒的EC 50 = 9.8 μM。知道这种 ferruginol 类似物对2型登革热病毒（EC 50 = 1.4 μM，DENV-2）也有活性，我们可以得出结论
• 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.