12α-acetoxy-5β-cholan-24-oic acid-3-spiro-6'-(1',2',4',5'-tetraoxacyclohexane)-3'-spirocyclohexane | 956495-54-8

• 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: 12α-acetoxy-5β-cholan-24-oic acid-3-spiro-6'-(1',2',4',5'-tetraoxacyclohexane)-3'-spirocyclohexane
• CAS: 956495-54-8
• 化学式: C₃₂H₅₀O₈
• 分子量: 562.744
• InChiKey: CHLMOZPCWMPLKG-YSSIKYIBSA-N

物化性质

• 沸点：
  628.9±55.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  12α-acetoxy-5β-cholan-24-oic acid-3-spiro-6'-(1',2',4',5'-tetraoxacyclohexane)-3'-spirocyclohexane 在 氯甲酸乙酯 、 三乙胺 、 盐酸肼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以63%的产率得到12α-acetoxy-5β-cholan-24-hydrazide-3-spiro-6'-(1',2',4',5'-tetraoxacyclohexane)-3'-spirocyclohexane
  参考文献：
  名称：

  Deoxycholic Acid-Derived Tetraoxane Antimalarials and Antiproliferatives

  摘要：

  The synthesis of deoxycholic acid (DCA)- and cholic acid (CA)-derived mixed tetraoxanes revealed that N-(2-dimethylamino)ethyl derivatives are potent antimalarials in vitro and in vivo. The tetraoxanes presented in this paper are dual inhibitors: besides curing mice in vivo without observed toxic effects, they kill cancer cell lines at very low concentrations. For example, DCA and CA derivatives 16 and 25 cured 3/5 (160 mg/kg/day) and 2/5 (40 mg/kg/day, MTD >960 mg/kg), respectively, and they were extremely active against melanoma LOX IMVI cancer, LC50 = 22 nM and 69 nM, respectively.

  DOI：

  10.1021/jm070684m
• 作为产物：
  描述：

  methyl 12α-acetoxy-5β-cholan-24-oate-3-spiro-6'-(1',2',4',5'-tetraoxacyclohexane)-3'-spirocyclohexane 在 sodium hydroxide 作用下， 以 水 、 异丙醇 为溶剂， 以92%的产率得到12α-acetoxy-5β-cholan-24-oic acid-3-spiro-6'-(1',2',4',5'-tetraoxacyclohexane)-3'-spirocyclohexane
  参考文献：
  名称：

  Deoxycholic Acid-Derived Tetraoxane Antimalarials and Antiproliferatives

  摘要：

  The synthesis of deoxycholic acid (DCA)- and cholic acid (CA)-derived mixed tetraoxanes revealed that N-(2-dimethylamino)ethyl derivatives are potent antimalarials in vitro and in vivo. The tetraoxanes presented in this paper are dual inhibitors: besides curing mice in vivo without observed toxic effects, they kill cancer cell lines at very low concentrations. For example, DCA and CA derivatives 16 and 25 cured 3/5 (160 mg/kg/day) and 2/5 (40 mg/kg/day, MTD >960 mg/kg), respectively, and they were extremely active against melanoma LOX IMVI cancer, LC50 = 22 nM and 69 nM, respectively.

  DOI：

  10.1021/jm070684m

文献信息

• Deoxycholic Acid-Derived Tetraoxane Antimalarials and Antiproliferatives
  作者：Nataša Terzić、Dejan Opsenica、Dragana Milić、Bernard Tinant、Kirsten S. Smith、Wilbur K. Milhous、Bogdan A. Šolaja

  DOI：10.1021/jm070684m

  日期：2007.10.1

  The synthesis of deoxycholic acid (DCA)- and cholic acid (CA)-derived mixed tetraoxanes revealed that N-(2-dimethylamino)ethyl derivatives are potent antimalarials in vitro and in vivo. The tetraoxanes presented in this paper are dual inhibitors: besides curing mice in vivo without observed toxic effects, they kill cancer cell lines at very low concentrations. For example, DCA and CA derivatives 16 and 25 cured 3/5 (160 mg/kg/day) and 2/5 (40 mg/kg/day, MTD >960 mg/kg), respectively, and they were extremely active against melanoma LOX IMVI cancer, LC50 = 22 nM and 69 nM, respectively.