methyl (Z)-14-methyl-11-pentadecenate | 64219-53-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (Z)-14-methyl-11-pentadecenate
• 英文别名: (Z)-14-Methyl-11-pentadecensaeuremethylester；methyl (Z)-14-methylpentadec-11-enoate
• CAS: 64219-53-0
• 化学式: C₁₇H₃₂O₂
• 分子量: 268.44
• InChiKey: JRDDBQWIKMAQST-BENRWUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (Z)-14-methyl-11-pentadecenate 在 palladium on activated charcoal 氢气 作用下， 生成 异十六烷酸
  参考文献：
  名称：

  Antitumor septacidin analogs

  摘要：

  In the first approach by total synthesis to the structure of the antitumor antibiotic septacidin, analogues have been obtained which show similar inhibition of RNA-DNA synthesis in cultured leukemia L1210 cells and similar activity against transplanted leukemia P388 in mice. In these analogues, the natural aminoheptose moiety is replaced by 4-amino-4-deoxy-and 4-amino-4,6-dideoxy-L-glucose, to retain the natural configuration of the pyranose ring. Also retained is the lipophilic fatty acid-amino acid side chain attached to the 4-amino group and glycosylation at the 6-NH2 of adenine. If the fatty acid chain was shortened from C16 to C6, if the fatty chain was shifted to the glycine unit, or if the glycine unit was omitted, activity was completely lost. However, activity was retained if the C16 chain was shortened only to C12 or if the glycine unit was extended to beta-alanine. Both active and inactive analogues were nonbinding to DNA and nonmutagenic to Salmonella strains. The synthetic approach was to start with a suitably protected sugar (L-fucose and L-galactose), construct the adenine moiety at C-1 introduce a 4-amino group, and finally attach the preformed side chain.

  DOI：

  10.1021/jm00221a002
• 作为产物：
  描述：

  11-溴十一酸 生成 methyl (Z)-14-methyl-11-pentadecenate
  参考文献：
  名称：

  Antitumor septacidin analogs

  摘要：

  In the first approach by total synthesis to the structure of the antitumor antibiotic septacidin, analogues have been obtained which show similar inhibition of RNA-DNA synthesis in cultured leukemia L1210 cells and similar activity against transplanted leukemia P388 in mice. In these analogues, the natural aminoheptose moiety is replaced by 4-amino-4-deoxy-and 4-amino-4,6-dideoxy-L-glucose, to retain the natural configuration of the pyranose ring. Also retained is the lipophilic fatty acid-amino acid side chain attached to the 4-amino group and glycosylation at the 6-NH2 of adenine. If the fatty acid chain was shortened from C16 to C6, if the fatty chain was shifted to the glycine unit, or if the glycine unit was omitted, activity was completely lost. However, activity was retained if the C16 chain was shortened only to C12 or if the glycine unit was extended to beta-alanine. Both active and inactive analogues were nonbinding to DNA and nonmutagenic to Salmonella strains. The synthetic approach was to start with a suitably protected sugar (L-fucose and L-galactose), construct the adenine moiety at C-1 introduce a 4-amino group, and finally attach the preformed side chain.

  DOI：

  10.1021/jm00221a002

文献信息

• Septacidin analogs
  申请人：Stanford Research Institute

  公开号：US04086416A1

  公开（公告）日：1978-04-25

  Septacidin analogs, useful as antitumor agents, having the structure ##STR1## where R is a branched or straight chain alkanoyl group of from 12 to 16 carbon atoms. A preferred compound is 6-[4,6-dideoxy-4-(isopalmitoylglycyl)-amino-.beta.-L-glucopyranosylamino]- 9H-purine.

  Septacidin类似物是一种有用的抗肿瘤剂，其结构式为##STR1##其中R为12至16个碳原子的支链或直链烷酰基。优选化合物为6-[4,6-二脱氧-4-(异棕榈酰甘氨酸基)-氨基-.beta.-L-葡萄糖吡喃糖基]-9H-嘌呤。