Trisnorsqualene thiol | 118599-21-6

• 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: Trisnorsqualene thiol
• 英文别名: (4E,8E,12E,16E)-4,8,13,17,21-pentamethyl-4,8,12,16,20-docosapentaen-1-thiol；(4E,8E,12E,16E)-4,8,13,17,21-pentamethyldocosa-4,8,12,16,20-pentaene-1-thiol
• CAS: 118599-21-6
• 化学式: C₂₇H₄₆S
• 分子量: 402.728
• InChiKey: ZEYJLNOFEFYYNS-OGDZRKEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  28
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2'-二硫二吡啶 、 Trisnorsqualene thiol 以 乙醇 为溶剂， 以63%的产率得到2-<(4E,8E,12E,16E)-4,8,13,17,21-pentamethyl-4,8,12,16,20-docosapentaenyldisulfamyl> pyridine
  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 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 三苯基膦 、 硫代乙酸 作用下， 生成 Trisnorsqualene thiol
  参考文献：
  名称：

  Trisnorsqualene alcohol, a potent inhibitor of vertebrate squalene epoxidase

  摘要：

  DOI：

  10.1021/ja00186a062

文献信息

• Trisnorsqualene alcohol, a potent inhibitor of vertebrate squalene epoxidase
  作者：Stephanie E. Sen、Glenn D. Prestwich

  DOI：10.1021/ja00186a062

  日期：1989.2
• SEN, STEPHANIE E.;PRESTWICH, GLENN D., J. AMER. CHEM. SOC., 111,(1989) N, C. 1508-1510
  作者：SEN, STEPHANIE E.、PRESTWICH, GLENN D.

  DOI：——

  日期：——
• 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.