(1S,4aR,5S,8aR)-methyl 5-(2-{2-[2-(2-chloroacetyl)aminomethyl]furan-3-yl}ethyl)-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylate | 1369538-20-4

• 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-(2-chloroacetyl)aminomethyl]furan-3-yl}ethyl)-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylate
• 英文别名: methyl 16-(chloroacetylaminomethyl)lambertianate
• CAS: 1369538-20-4
• 化学式: C₂₄H₃₄ClNO₄
• 分子量: 435.991
• InChiKey: YHNYLZCMHYLWBB-LTLLVOOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  68.54
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,4aR,5S,8aR)-methyl 5-(2-{2-[2-(2-chloroacetyl)aminomethyl]furan-3-yl}ethyl)-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylate 、 3-苯基-3-氨基丙酸甲酯盐酸盐 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以67%的产率得到(1S,4aR,5S,8aR)-methyl 5-{2-[2-({2-[(3-methoxycarbonyl-1-phenylpropyl)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
• 作为产物：
  描述：

  methyl 16-formyllambertianate 在 盐酸羟胺 、 氢气 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 (1S,4aR,5S,8aR)-methyl 5-(2-{2-[2-(2-chloroacetyl)aminomethyl]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