(1S,4aR,5S,8aR)-5-[2'-(5'',8''-diacetoxy-naphthalen-2''-yl)-ethyl]-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylic acid methyl ester | 177327-09-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S,4aR,5S,8aR)-5-[2'-(5'',8''-diacetoxy-naphthalen-2''-yl)-ethyl]-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylic acid methyl ester
• 英文别名: 6-[14-methoxy-14-oxo-drim-8(12)-en-11-yl-methyl]-naphthalene-1,4-diol diacetate；methyl (1S,4aR,5S,8aR)-5-[2-(5,8-diacetyloxynaphthalen-2-yl)ethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
• CAS: 177327-09-2
• 化学式: C₃₁H₃₈O₆
• 分子量: 506.639
• InChiKey: QHOFXURIEDCCOX-YXWCJEOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,4aR,5S,8aR)-5-[2'-(5'',8''-diacetoxy-naphthalen-2''-yl)-ethyl]-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylic acid methyl ester 在 氢碘酸 作用下， 以 水 、 苯 为溶剂， 反应 0.17h， 以98%的产率得到methyl (1S,4aS,8aR)-5-[2-(5,8-diacetyloxynaphthalen-2-yl)ethyl]-1,4a,6-trimethyl-2,3,4,7,8,8a-hexahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  New cytotoxic diterpenylnaphthohydroquinone derivatives obtained from a natural diterpenoid

  摘要：

  Diterpenylquinone/hydroquinone derivatives were prepared through Diels-Alder cycloaddition between natural myrcecommunic acid or its methyl ester and p-benzoquinone (p-BQ), using BF3 center dot Et2O as catalyst or under microwave (Mw) irradiation. Acetyl, methyl and benzyl derivatives of several diterpenyinaplithohydroquinone were prepared from cycloadducts following two basic synthetic strategies, either protection before aromatisation or viceversa. Some of them were further functionalised at the B-ring of the decaline core. Most of the new compounds were evaluated and some of them resulted cytotoxic against several tumour cell lines with IC50 values tinder the mu M level. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.005
• 作为产物：
  描述：

  (1S,4aR,5S,8aR)-5-[2'-(5'',8''-dihydroxy-1'',4''-dihydronaphthalen-2''-yl)-ethyl]-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylic acid methyl ester 在 吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醚 为溶剂， 生成 (1S,4aR,5S,8aR)-5-[2'-(5'',8''-diacetoxy-naphthalen-2''-yl)-ethyl]-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  新的选择性细胞毒性二萜烯醌和二萜烯对苯二酚。

  摘要：

  通过在三个拉丹二萜类化合物（肉豆蔻酸，甲基肉豆蔻酸甲酯和肉豆蔻酸乙酸酯）和对苯醌或1,4-萘醌之间的狄尔斯-阿尔德环加成反应制备了一系列新的二萜烯醌/对苯二酚。考虑到对肿瘤细胞的细胞毒性以及这些二萜烯基萘醌/对苯二酚和蒽醌的选择性，考虑了醌/对苯二酚片段和其他结构特征（如萜烯核中不同功能）的影响。几种化合物在微摩尔水平下显示出IC50值，在NCI筛选小组中评估了其中的四种衍生物。结果显示出对肾癌细胞系的重要选择性，将这些化合物鉴定为非常有希望的抗肿瘤药。

  DOI：

  10.1021/jm001048q

文献信息

• New Antineoplastic Naphthohydroquinones Attached to Labdane and Rearranged Diterpene Skeletons
  作者：Ángela P. Hernández、Pablo Chamorro、Mª Lucena Rodríguez、José M. Miguel del Corral、Pablo A. García、Andrés Francesch、Arturo San Feliciano、Mª Ángeles Castro

  DOI：10.3390/molecules26020474

  日期：——

  through induction of biomimetic breaks and rearrangements of the diterpene skeleton. All the isomers generated were completely characterized by spectroscopic procedures. The resulting compounds have been tested in vitro on cultured cancer cells, showing their relevant antineoplastic cytotoxicity, with GI50 values in the μM and sub-μM range. The rearranged compound 8 showed the best cytotoxic results

  萜烯醌是自然界中广泛存在的混合生物发生初级或次级代谢物，具有许多生物活性，包括抗肿瘤细胞毒性，激发了这项工作。在这里，我们提出了几种二萜氢醌 (DTHQ) 衍生物的细胞毒性结构-活性关系，这些衍生物是从用作起始材料的天然拉丹二萜类 myrceocommunic 酸中获得的。通过环氧化、臭氧分解或脱羧，以及通过诱导二萜骨架的仿生断裂和重排，在双环核心上实施了不同的结构修饰，改变了十氢化萘的功能和立体化学。所有产生的异构体都通过光谱程序完全表征。所得化合物已在体外培养的癌细胞上进行了测试，显示其相关的抗肿瘤细胞毒性，GI50 值在 μM 和亚 μM 范围内。重排的化合物 8 显示出最好的细胞毒性结果，GI50 在亚微摩尔范围内，保留了母体化合物的细胞毒性水平。在这份报告中，证明了拉丹烷骨架在化学转化方面的多功能性以及继续使用结构修饰来获得新的生物活性化合物的兴趣。
• New cytotoxic diterpenylnaphthohydroquinone derivatives obtained from a natural diterpenoid
  作者：José M. Miguel del Corral、M. Angeles Castro、M. Lucena Rodrı´guez、Pablo Chamorro、Carmen Cuevas、Arturo San Feliciano

  DOI：10.1016/j.bmc.2007.06.005

  日期：2007.9.1

  Diterpenylquinone/hydroquinone derivatives were prepared through Diels-Alder cycloaddition between natural myrcecommunic acid or its methyl ester and p-benzoquinone (p-BQ), using BF3 center dot Et2O as catalyst or under microwave (Mw) irradiation. Acetyl, methyl and benzyl derivatives of several diterpenyinaplithohydroquinone were prepared from cycloadducts following two basic synthetic strategies, either protection before aromatisation or viceversa. Some of them were further functionalised at the B-ring of the decaline core. Most of the new compounds were evaluated and some of them resulted cytotoxic against several tumour cell lines with IC50 values tinder the mu M level. (c) 2007 Elsevier Ltd. All rights reserved.
• New Selective Cytotoxic Diterpenylquinones and Diterpenylhydroquinones
  作者：José M Miguel del Corral、Marina Gordaliza、M Angeles Castro、M Mar Mahiques、Pablo Chamorro、Aurora Molinari、M Dolores García-Grávalos、Howard B. Broughton、Arturo San Feliciano

  DOI：10.1021/jm001048q

  日期：2001.4.1

  considered in relation to the cytotoxicity toward neoplastic cells and the selectivity of these diterpenylnaphthoquinones/hydroquinones and anthraquinones. Several compounds showed IC50 values under the micromolar level, and four of these derivatives were evaluated at the NCI screening panel. The results showed an important selectivity toward renal cancer lines, identifying these compounds as a very promising

  通过在三个拉丹二萜类化合物（肉豆蔻酸，甲基肉豆蔻酸甲酯和肉豆蔻酸乙酸酯）和对苯醌或1,4-萘醌之间的狄尔斯-阿尔德环加成反应制备了一系列新的二萜烯醌/对苯二酚。考虑到对肿瘤细胞的细胞毒性以及这些二萜烯基萘醌/对苯二酚和蒽醌的选择性，考虑了醌/对苯二酚片段和其他结构特征（如萜烯核中不同功能）的影响。几种化合物在微摩尔水平下显示出IC50值，在NCI筛选小组中评估了其中的四种衍生物。结果显示出对肾癌细胞系的重要选择性，将这些化合物鉴定为非常有希望的抗肿瘤药。
• An easy route to pentacyclic terpenylquinones
  作者：M. Angeles Castro、José M. Miguel del Corral、M. Lucena Rodríguez、Arturo San Feliciano

  DOI：10.1016/j.tetlet.2011.11.080

  日期：2012.2

  Cyclisation of terpenylnaphthohydroquinone derivatives or terpenylquinone cycloadducts, obtained from methyl myrcecommunate, was performed in the presence of HI, I-2 or BF3 center dot OEt2 and provides efficient synthetic strategies for the preparation of pentacyclic terpenylquinones. (C) 2011 Elsevier Ltd. All rights reserved.