methyl 3-(9-aminononanoyl)amino-3-phenylpropionate hydrochloride | 1159685-98-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 3-(9-aminononanoyl)amino-3-phenylpropionate hydrochloride
• 英文别名: Methyl n-(9-aminononanoyl)-3-amino-3-phenylpropionate hydrochloride；methyl 3-(9-aminononanoylamino)-3-phenylpropanoate;hydrochloride
• CAS: 1159685-98-9
• 化学式: C₁₉H₃₀N₂O₃*ClH
• 分子量: 370.92
• InChiKey: FUNTWHILTBQBFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  81.4
• 氢给体数：
  3
• 氢受体数：
  4

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 、 methyl 3-(9-aminononanoyl)amino-3-phenylpropionate hydrochloride 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以39%的产率得到(1S,4aR,5S,8aR)-methyl 1,4a-dimethyl-6-methylene-5-{2-[2-(3,14,18-trioxo-16-phenyl-19-oxa-2,5,15-triazaicosyl)furan-3-yl]ethyl}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