(4E,8E,12E,16E)-4,8,13,17,21-pentamethyl-4,8,12,16,20-docosapentaenyl azide | 138325-49-2

• 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,16E)-4,8,13,17,21-pentamethyl-4,8,12,16,20-docosapentaenyl azide
• 英文别名: (4e,8e,12e,16e)-4,8,13,17,21-Penta-methyl-4,8,12,16,20-docosapentaenyl azide；(6E,10E,14E,18E)-22-azido-2,6,10,15,19-pentamethyldocosa-2,6,10,14,18-pentaene
• CAS: 138325-49-2
• 化学式: C₂₇H₄₅N₃
• 分子量: 411.674
• InChiKey: YPZDRIZIFOIVDJ-OGDZRKEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  30
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4E,8E,12E,16E)-4,8,13,17,21-pentamethyl-4,8,12,16,20-docosapentaenyl azide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以72%的产率得到(4E,8E,12E,16E)-4,8,13,17,21-pentamethyl-4,8,12,16,20-docosapentaenyl amine
  参考文献：
  名称：

  Synthesis and biological activity of a squalenoid maleimide and other classes of squalene derivatives as irreversible inhibitors of 2,3-oxidosqualene cyclase

  摘要：

  New classes of squalene derivatives were rationally designed and synthesized as irreversible inhibitors of 2,3-oxido-squalene cyclase (OSC), a key enzyme in sterol biosynthesis. The derivatives synthesized were maleimide 5, disulfides 8-9, alpha,beta-unsaturated nitriles 10-11 and oxirane 12. The inhibitor activities of these derivatives were determined in vitro on OSC associated with pig liver microsomes. Squalene and dodecyl maleimide were the best inhibitors of OSC, showing a time-dependent enzyme from squalene maleimide inactivation whereas the dodecyl derivative did not. This fact and the complex kinetics shown by squalene maleimide suggest the presence of different classes of thiolic groups essential to the activity of OSC.

  DOI：

  10.1016/0223-5234(94)90121-x
• 作为产物：
  描述：

  1,1',2-trisnorsqualene alcohol 在 Zn(N3)2-2 pyr 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以90%的产率得到(4E,8E,12E,16E)-4,8,13,17,21-pentamethyl-4,8,12,16,20-docosapentaenyl azide
  参考文献：
  名称：

  Synthesis and biological activity of a squalenoid maleimide and other classes of squalene derivatives as irreversible inhibitors of 2,3-oxidosqualene cyclase

  摘要：

  New classes of squalene derivatives were rationally designed and synthesized as irreversible inhibitors of 2,3-oxido-squalene cyclase (OSC), a key enzyme in sterol biosynthesis. The derivatives synthesized were maleimide 5, disulfides 8-9, alpha,beta-unsaturated nitriles 10-11 and oxirane 12. The inhibitor activities of these derivatives were determined in vitro on OSC associated with pig liver microsomes. Squalene and dodecyl maleimide were the best inhibitors of OSC, showing a time-dependent enzyme from squalene maleimide inactivation whereas the dodecyl derivative did not. This fact and the complex kinetics shown by squalene maleimide suggest the presence of different classes of thiolic groups essential to the activity of OSC.

  DOI：

  10.1016/0223-5234(94)90121-x

文献信息

• Synthesis and biological activity of a squalenoid maleimide and other classes of squalene derivatives as irreversible inhibitors of 2,3-oxidosqualene cyclase
  作者：G Grosa、F Viola、M Ceruti、P Brusa、L Delprino、F Dosio、L Cattel

  DOI：10.1016/0223-5234(94)90121-x

  日期：1994.1

  New classes of squalene derivatives were rationally designed and synthesized as irreversible inhibitors of 2,3-oxido-squalene cyclase (OSC), a key enzyme in sterol biosynthesis. The derivatives synthesized were maleimide 5, disulfides 8-9, alpha,beta-unsaturated nitriles 10-11 and oxirane 12. The inhibitor activities of these derivatives were determined in vitro on OSC associated with pig liver microsomes. Squalene and dodecyl maleimide were the best inhibitors of OSC, showing a time-dependent enzyme from squalene maleimide inactivation whereas the dodecyl derivative did not. This fact and the complex kinetics shown by squalene maleimide suggest the presence of different classes of thiolic groups essential to the activity of OSC.