3β-acetoxy-23,24-bisnor-chol-5-en-22-(methyl butanoate) amine | 913338-38-2

• 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-23,24-bisnor-chol-5-en-22-(methyl butanoate) amine
• 英文别名: methyl 4-[[(2S)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-acetyloxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino]butanoate
• CAS: 913338-38-2
• 化学式: C₂₉H₄₇NO₄
• 分子量: 473.696
• InChiKey: RAACUKXVGINMTN-HSIBUNQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-23,24-bisnor-chol-5-en-22-(methyl butanoate) amine 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 4-[[(2S)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino]butanoic acid
  参考文献：
  名称：

  Evaluation of Azasterols as Anti-Parasitics

  摘要：

  In this article, the design and synthesis of some novel azasterols is described, followed by their evaluation against Trypanosoma brucei rhodesiense, T. cruzi, Leishmania donovani, and Plasmodium falciparum, the causative agents of human African trypanosomiasis, Chagas disease, leishmaniasis, and malaria, respectively. Some of the compounds showed anti-parasitic activity. In particular, a number of compounds appeared to very potently inhibit the growth of the blood stream form T. b. rhodesiense, with one compound giving an IC50 value of 12 nM. Clear structure activity relationships could be discerned. These compounds represent important leads for further optimization. Azasterols have previously been shown to inhibit sterol biosynthesis in T. cruzi and L. donovani by the inhibition of the enzyme sterol 24-methyltransferase. However, in this case, none of the compounds showed inhibition of the enzyme. Therefore, these compounds have an unknown mode of action.

  DOI：

  10.1021/jm060290f
• 作为产物：
  描述：

  3β-acetoxy-23,24-bisnor-chol-5-en-22-ol 在 3 A molecular sieve 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 3β-acetoxy-23,24-bisnor-chol-5-en-22-(methyl butanoate) amine
  参考文献：
  名称：

  Evaluation of Azasterols as Anti-Parasitics

  摘要：

  In this article, the design and synthesis of some novel azasterols is described, followed by their evaluation against Trypanosoma brucei rhodesiense, T. cruzi, Leishmania donovani, and Plasmodium falciparum, the causative agents of human African trypanosomiasis, Chagas disease, leishmaniasis, and malaria, respectively. Some of the compounds showed anti-parasitic activity. In particular, a number of compounds appeared to very potently inhibit the growth of the blood stream form T. b. rhodesiense, with one compound giving an IC50 value of 12 nM. Clear structure activity relationships could be discerned. These compounds represent important leads for further optimization. Azasterols have previously been shown to inhibit sterol biosynthesis in T. cruzi and L. donovani by the inhibition of the enzyme sterol 24-methyltransferase. However, in this case, none of the compounds showed inhibition of the enzyme. Therefore, these compounds have an unknown mode of action.

  DOI：

  10.1021/jm060290f

文献信息

• Evaluation of Azasterols as Anti-Parasitics
  作者：Ludovic Gros、Silvia Orenes Lorente、Jimenez、Vanessa Yardley、Lauren Rattray、Hayley Wharton、Susan Little、Simon L. Croft、Luis M. Ruiz-Perez、Dolores Gonzalez-Pacanowska、Ian H. Gilbert

  DOI：10.1021/jm060290f

  日期：2006.10.1

  In this article, the design and synthesis of some novel azasterols is described, followed by their evaluation against Trypanosoma brucei rhodesiense, T. cruzi, Leishmania donovani, and Plasmodium falciparum, the causative agents of human African trypanosomiasis, Chagas disease, leishmaniasis, and malaria, respectively. Some of the compounds showed anti-parasitic activity. In particular, a number of compounds appeared to very potently inhibit the growth of the blood stream form T. b. rhodesiense, with one compound giving an IC50 value of 12 nM. Clear structure activity relationships could be discerned. These compounds represent important leads for further optimization. Azasterols have previously been shown to inhibit sterol biosynthesis in T. cruzi and L. donovani by the inhibition of the enzyme sterol 24-methyltransferase. However, in this case, none of the compounds showed inhibition of the enzyme. Therefore, these compounds have an unknown mode of action.