(1S,4aR,5S,8aR)-methyl 5-{2-[2-({2-[(1-methoxycarbonyl-3-methylbutan-2-yl)amino]acetylamino}methyl)furan-3-yl]ethyl}-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylate | 1369538-33-9

• 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: (1S,4aR,5S,8aR)-methyl 5-{2-[2-({2-[(1-methoxycarbonyl-3-methylbutan-2-yl)amino]acetylamino}methyl)furan-3-yl]ethyl}-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylate
• CAS: 1369538-33-9
• 化学式: C₃₀H₄₆N₂O₆
• 分子量: 530.705
• InChiKey: JMDGXQDBQJCCFA-WRPDNJHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  106.87
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  (1S,4aR,5S,8aR)-methyl 5-{2-[2-(aminomethyl)furan-3-yl]ethyl}-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylate 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 26.0h， 生成 (1S,4aR,5S,8aR)-methyl 5-{2-[2-({2-[(1-methoxycarbonyl-3-methylbutan-2-yl)amino]acetylamino}methyl)furan-3-yl]ethyl}-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  Synthetic transformations of higher terpenoids. XXVI. 16-acetylaminomethyllabdanoids and their cytotoxicity

  摘要：

  Coupling of methyl 16-aminomethyllambertianate with N-Boc-protected omega-amino acids resulted in 16-(N-Boc-aminononan)- and 16-(N-Boc-aminoundecan)amidomethyllabdanoids. Interaction of methyl aminomethyllambertianate with bicyclo[2.2.1]hept-5-en-2,3-dicarboxylic acid anhydride led to the amide of bicyclo[2.2.1]heptan-1,2-dicarboxylic acid with a labdanoid substituent. Reaction of methyl 16-aminomethyllambertianate with chloroacetyl chloride resulted in methyl 16-(chloroacetylaminomethyl)lambertianate; coupling of the latter with methyl esters of amino acids gave the corresponding amides of methyl lambertianate. The compounds obtained were more cytotoxic toward CEM-13, MT-4, and U-937 tumor cell lines as compared with lambertianic acid; the dose inhibiting tumor cell viability by 50% (CCID50) of the more active compounds was 3.9-9.9 mu M.

  DOI：

  10.1134/s1068162011060082