(1S,4aR,5S,8aR)-methyl 5-{2-[2-(aminomethyl)furan-3-yl]ethyl}-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylate | 1262044-69-8

• 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-(aminomethyl)furan-3-yl]ethyl}-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylate
• 英文别名: methyl 16-(aminomethyl)lambertianate；methyl 16-aminomethyllambertianate；methyl (1S,4aR,5S,8aR)-5-[2-[2-(aminomethyl)furan-3-yl]ethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
• CAS: 1262044-69-8
• 化学式: C₂₂H₃₃NO₃
• 分子量: 359.509
• InChiKey: YVRGGQGTYCXNRE-GWWHBBDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (1S,4aR,5S,8aR)-methyl 5-{2-[2-({2-[((9-methoxycarbonyl)nonyl)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：

  (1S,4aR,5S,8aR)-methyl 5-(2-{2-[(E)-(hydroxyimino)methyl]furan-3-yl}ethyl)-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylate 在 氢气 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以97%的产率得到(1S,4aR,5S,8aR)-methyl 5-{2-[2-(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

文献信息

• Synthetic transformations of higher terpenoids: XXIX. Gold catalyzed cycloisomerization of propargylaminomethyl substituted and propargyloxymethyl substituted furanolabdanoids
  作者：Yu. V. Kharitonov、E. E. Shults、M. M. Shakirov、I. Yu. Bagryanskaya、G. A. Tolstikov

  DOI：10.1134/s1070428012080088

  日期：2012.8

  16-Propargylaminomethyl substituted and 16-propargyloxymethyl substituted furanolabdanoids were synthesized, which under the action of AuCl3 in acetonitrile underwent cycloisomerization forming 7-hydroxyisoindolines or 7-hydroxydihydroisobenzofurans substituted by a terpenoid fragment.
• Synthetic transformations of higher terpenoids. XXVI. 16-acetylaminomethyllabdanoids and their cytotoxicity
  作者：Yu. V. Kharitonov、E. E. Shul’ts、M. M. Shakirov、M. A. Pokrovsky、A. G. Pokrovsky、G. A. Tolstikov

  DOI：10.1134/s1068162011060082

  日期：2012.1

  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.