3β-acetoxy-22-[(6-aminohexyl)amino]-22-oxo-23,24-bisnor-chol-5-ene | 862719-26-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3β-acetoxy-22-[(6-aminohexyl)amino]-22-oxo-23,24-bisnor-chol-5-ene
• CAS: 862719-26-4
• 化学式: C₃₀H₅₀N₂O₃
• 分子量: 486.739
• InChiKey: OCMFNYBHTUHYIX-FUERFDGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  81.42
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-22-[(6-aminohexyl)amino]-22-oxo-23,24-bisnor-chol-5-ene 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以90%的产率得到3β-hydroxy-22-[(6-aminohexyl)amino]-22-oxo-23,24-bisnor-chol-5-ene
  参考文献：
  名称：

  Preparation of transition-state analogues of sterol 24-methyl transferase as potential anti-parasitics

  摘要：

  There is an urgent need for new drugs to treat leishmaniasis and Chagas disease. One important drug target in these organisms is sterol biosynthesis. In these organisms the main endogenous sterols are ergosta- and stigmata-like compounds in contrast to the situation in mammals, which have cholesterol as the sole sterol. In this paper we discuss the design, synthesis and evaluation of potential transition state analogues of the enzyme Delta(24(25))-methyltransferase (24-SMT). This enzyme is essential for the biosynthesis of ergosterol, but not required for the biosynthesis of cholesterol. A series of compounds were successfully synthesised in which mimics of the S-adenosyl methionine co-factor were attached to the sterol nucleus. Compounds were evaluated against recombinant Leishmania major 24-SMT and the parasites L. donovani and Trypanosoma cruzi in vitro, causative organisms of leishmaniasis and Chagas disease, respectively. Some of the-compounds showed inhibition of the recombinant Leishmania major 24-SMT and induced growth inhibition of the parasites. Some compounds also showed anti-parasitic activity against L. donovani and T cruzi, but no inhibition of the enzyme. In addition, some of the compounds had anti-proliferative activity against the bloodstream forms of Trypanosoma brucei rhodesiense, which causes African trypanosomiasis. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2005.06.012
• 作为产物：
  描述：

  3β-acetoxybisnor-5-cholenic acid 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 3β-acetoxy-22-[(6-aminohexyl)amino]-22-oxo-23,24-bisnor-chol-5-ene
  参考文献：
  名称：

  Preparation of transition-state analogues of sterol 24-methyl transferase as potential anti-parasitics

  摘要：

  There is an urgent need for new drugs to treat leishmaniasis and Chagas disease. One important drug target in these organisms is sterol biosynthesis. In these organisms the main endogenous sterols are ergosta- and stigmata-like compounds in contrast to the situation in mammals, which have cholesterol as the sole sterol. In this paper we discuss the design, synthesis and evaluation of potential transition state analogues of the enzyme Delta(24(25))-methyltransferase (24-SMT). This enzyme is essential for the biosynthesis of ergosterol, but not required for the biosynthesis of cholesterol. A series of compounds were successfully synthesised in which mimics of the S-adenosyl methionine co-factor were attached to the sterol nucleus. Compounds were evaluated against recombinant Leishmania major 24-SMT and the parasites L. donovani and Trypanosoma cruzi in vitro, causative organisms of leishmaniasis and Chagas disease, respectively. Some of the-compounds showed inhibition of the recombinant Leishmania major 24-SMT and induced growth inhibition of the parasites. Some compounds also showed anti-parasitic activity against L. donovani and T cruzi, but no inhibition of the enzyme. In addition, some of the compounds had anti-proliferative activity against the bloodstream forms of Trypanosoma brucei rhodesiense, which causes African trypanosomiasis. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2005.06.012