3-[4'-(tert-Butyl-dimethyl-silanyloxy)-biphenyl-4-yl]-1-aza-bicyclo[2.2.2]octan-3-ol | 854519-85-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-[4'-(tert-Butyl-dimethyl-silanyloxy)-biphenyl-4-yl]-1-aza-bicyclo[2.2.2]octan-3-ol
• CAS: 854519-85-0
• 化学式: C₂₅H₃₅NO₂Si
• 分子量: 409.644
• InChiKey: NMCGSIOJHYEVPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  32.7
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-[4'-(tert-Butyl-dimethyl-silanyloxy)-biphenyl-4-yl]-1-aza-bicyclo[2.2.2]octan-3-ol 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以48%的产率得到4'-(1-Aza-bicyclo[2.2.2]oct-2-en-3-yl)-biphenyl-4-ol
  参考文献：
  名称：

  Biphenylquinuclidines as inhibitors of squalene synthase and growth of parasitic protozoa

  摘要：

  In this paper we describe the preparation of some biphenylquinuclidine derivatives and their evaluation as inhibitors of squalene synthase in order to explore their potential in the treatment of the parasitic diseases leishmaniasis and Chagas disease. The compounds were screened against recombinant Leishmania major squalene synthase and against Leishmania mexicana promastigotes, Leishmania donovani intracellular amastigotes and Trypanosoma cruzi intracellular amastigotes. Compounds that inhibited the enzyme, also reduced the levels of steroids and caused growth inhibition of L. mexicana promastigotes. However there was a lower correlation between inhibition of the enzyme and growth inhibition of the intracellular parasites, possibly due to delivery problems. Some compounds also showed growth inhibition of T brucei rhodesiense trypomastigotes, although in this case alternative modes of action other than inhibition of SQS are probably involved. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.060
• 作为产物：
  描述：

  4-羟基-4'-溴联苯 在 咪唑 、 仲丁基锂 作用下， 以 四氢呋喃 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.08h， 生成 3-[4'-(tert-Butyl-dimethyl-silanyloxy)-biphenyl-4-yl]-1-aza-bicyclo[2.2.2]octan-3-ol
  参考文献：
  名称：

  Biphenylquinuclidines as inhibitors of squalene synthase and growth of parasitic protozoa

  摘要：

  In this paper we describe the preparation of some biphenylquinuclidine derivatives and their evaluation as inhibitors of squalene synthase in order to explore their potential in the treatment of the parasitic diseases leishmaniasis and Chagas disease. The compounds were screened against recombinant Leishmania major squalene synthase and against Leishmania mexicana promastigotes, Leishmania donovani intracellular amastigotes and Trypanosoma cruzi intracellular amastigotes. Compounds that inhibited the enzyme, also reduced the levels of steroids and caused growth inhibition of L. mexicana promastigotes. However there was a lower correlation between inhibition of the enzyme and growth inhibition of the intracellular parasites, possibly due to delivery problems. Some compounds also showed growth inhibition of T brucei rhodesiense trypomastigotes, although in this case alternative modes of action other than inhibition of SQS are probably involved. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.060