(1S,4aR,5S,8aR)-5-[2'-(5'',8''-dioxo-5'',8''-dihydronaphthalen-2''-yl)-ethyl]-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylic acid methyl ester | 177326-94-2

• 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''-dioxo-5'',8''-dihydronaphthalen-2''-yl)-ethyl]-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylic acid methyl ester
• 英文别名: methyl (1S,4aR,5S,8aR)-5-[2-(5,8-dioxonaphthalen-2-yl)ethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
• CAS: 177326-94-2
• 化学式: C₂₇H₃₂O₄
• 分子量: 420.549
• InChiKey: RVNDPBRBSHYELR-MPYVGDORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  31
• 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：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 (1S,4aR,5S,8aR)-5-[2'-(5'',8''-dioxo-5'',8''-dihydronaphthalen-2''-yl)-ethyl]-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylic acid methyl ester 在 sodium dithionite 、 sodium hydride 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以67%的产率得到methyl (1S,4aR,5S,8aR)-5-[2-[5,8-bis(phenylmethoxy)naphthalen-2-yl]ethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-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：

  在 manganese(IV) oxide 作用下， 以 苯 为溶剂， 反应 16.0h， 以86%的产率得到(1S,4aR,5S,8aR)-5-[2'-(5'',8''-dioxo-5'',8''-dihydronaphthalen-2''-yl)-ethyl]-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylic acid methyl ester
  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

文献信息

• 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。
• 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.