(4E,8E,12E)-N-methyl-N-(4-methylpentyl)-16,17-epoxy-4,9,13,17-tetramethyl-4,8,12-octadecatrienylamine | 153280-28-5

• 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: (4E,8E,12E)-N-methyl-N-(4-methylpentyl)-16,17-epoxy-4,9,13,17-tetramethyl-4,8,12-octadecatrienylamine
• 英文别名: 19-aza-18,19,22,23-tetrahydrosqualene-2,3-epoxide；(4E,8E,12E)-15-(3,3-dimethyloxiran-2-yl)-N,4,9,13-tetramethyl-N-(4-methylpentyl)pentadeca-4,8,12-trien-1-amine
• CAS: 153280-28-5
• 化学式: C₂₉H₅₃NO
• 分子量: 431.746
• InChiKey: OQQRKGIMTZROAN-ZTIFRMFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  31
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  15.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4E,8E,12E)-N-methyl-N-(4-methylpentyl)-16,17-epoxy-4,9,13,17-tetramethyl-4,8,12-octadecatrienylamine 在 双氧水 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以74%的产率得到(4E,8E,12E)-N-methyl-N-(4-methylpentyl)-16,17-epoxy-4,9,13,17-tetramethyl-4,8,12-octadecatrienylamine N-oxide
  参考文献：
  名称：

  Synthesis and biological activity of 19-azasqualene 2,3-epoxide as inhibitor of 2,3-oxidosqualene cyclase

  摘要：

  19-Azasqualene 2,3-epoxide and its N-oxide, high-energy intermediate analogue inhibitors of 2,3-oxidosqualene (SO) cyclase, were obtained by total synthesis. These compounds were designed to mimic the C-20 carbonium ion precursor of lanosterol formed during SO cyclization. The synthesis involved the preparation Of C22 squalenoid aldehyde epoxide through a new procedure and the reconstruction of the squalenoid chain bearing a nitrogen at C-19 (pro C-20). 19-Azasqualene 2,3-epoxide was active on SO cyclase from rat and pig liver with an IC50 of 1.5 muM in pig, while in SO cyclases of yeast (S cerevisiae and C albicans) microsomes it was 20-30-fold less active. It was inactive on squalene epoxidase from rat and pig liver at the highest concentrations tested (100 muM).

  DOI：

  10.1016/0223-5234(93)90026-b
• 作为产物：
  描述：

  角鲨烯 在 N-溴代丁二酰亚胺(NBS) 、 水 、 sodium cyanoborohydride 、 potassium carbonate 、 过碘酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 (4E,8E,12E)-N-methyl-N-(4-methylpentyl)-16,17-epoxy-4,9,13,17-tetramethyl-4,8,12-octadecatrienylamine
  参考文献：
  名称：

  Synthesis and biological activity of 19-azasqualene 2,3-epoxide as inhibitor of 2,3-oxidosqualene cyclase

  摘要：

  19-Azasqualene 2,3-epoxide and its N-oxide, high-energy intermediate analogue inhibitors of 2,3-oxidosqualene (SO) cyclase, were obtained by total synthesis. These compounds were designed to mimic the C-20 carbonium ion precursor of lanosterol formed during SO cyclization. The synthesis involved the preparation Of C22 squalenoid aldehyde epoxide through a new procedure and the reconstruction of the squalenoid chain bearing a nitrogen at C-19 (pro C-20). 19-Azasqualene 2,3-epoxide was active on SO cyclase from rat and pig liver with an IC50 of 1.5 muM in pig, while in SO cyclases of yeast (S cerevisiae and C albicans) microsomes it was 20-30-fold less active. It was inactive on squalene epoxidase from rat and pig liver at the highest concentrations tested (100 muM).

  DOI：

  10.1016/0223-5234(93)90026-b

文献信息

• Synthesis and biological activity of 19-azasqualene 2,3-epoxide as inhibitor of 2,3-oxidosqualene cyclase
  作者：M Ceruti、F Rocco、F Viola、G Balliano、G Grosa、F Dosio、L Cattel

  DOI：10.1016/0223-5234(93)90026-b

  日期：1993.1

  19-Azasqualene 2,3-epoxide and its N-oxide, high-energy intermediate analogue inhibitors of 2,3-oxidosqualene (SO) cyclase, were obtained by total synthesis. These compounds were designed to mimic the C-20 carbonium ion precursor of lanosterol formed during SO cyclization. The synthesis involved the preparation Of C22 squalenoid aldehyde epoxide through a new procedure and the reconstruction of the squalenoid chain bearing a nitrogen at C-19 (pro C-20). 19-Azasqualene 2,3-epoxide was active on SO cyclase from rat and pig liver with an IC50 of 1.5 muM in pig, while in SO cyclases of yeast (S cerevisiae and C albicans) microsomes it was 20-30-fold less active. It was inactive on squalene epoxidase from rat and pig liver at the highest concentrations tested (100 muM).