spiro[7α,12α-diacetoxy-5β-cholan-24-oic acid-3,6'-(3',3'-dimethyl-1',2',4',5'-tetraoxacyclohexane)] | 1059184-72-3

• 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: spiro[7α,12α-diacetoxy-5β-cholan-24-oic acid-3,6'-(3',3'-dimethyl-1',2',4',5'-tetraoxacyclohexane)]
• 英文别名: (4R)-4-[(5R,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-diacetyloxy-6',6',10,13-tetramethylspiro[1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,3'-1,2,4,5-tetraoxane]-17-yl]pentanoic acid
• CAS: 1059184-72-3
• 化学式: C₃₁H₄₈O₁₀
• 分子量: 580.716
• InChiKey: MFFLTSFHHILDEN-VZDSLEPXSA-N

物化性质

• 熔点：
  195-197 °C
• 沸点：
  615.1±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  spiro[7α,12α-diacetoxy-5β-cholan-24-oic acid-3,6'-(3',3'-dimethyl-1',2',4',5'-tetraoxacyclohexane)] 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59%的产率得到spiro[7α,12α-diacetoxy-5β-cholane-24-hydrazide-3,6'-(3',3'-dimethyl-1',2',4',5'-tetraoxacyclohexane)]
  参考文献：
  名称：

  Mixed tetraoxanes containing the acetone subunit as antimalarials

  摘要：

  Eleven new tetraoxanes possessing cholic acid-derived carrier and isopropylidene moiety were synthesized and were tested in vitro and in vivo. In vitro screening revealed that nine of them were more potent against CQ-resistant W2 than CQ-susceptible D6 strain and that two of them were equally or more potent than artemisinin and mefloquine against multi- drug resistant TM91C235 strain. Amine 8 cured all mice at the dose of 160 mg/kg/day, while the anilide 9 exhibited MCD <= 20 mg/kg/day. The diol 13 was most potent antiproliferative with GI(50), TGI, LC50 MG_MID 0.98 mu M, 3.80 mu M, 11.22 mu M, respectively. All tested compounds showed no toxic effects. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.017
• 作为产物：
  描述：

  spiro[methyl 7α,12α-diacetoxy-5β-cholan-24-oate-3,6'-(3',3'-dimethyl-1',2',4',5'-tetraoxacyclohexane)] 在 sodium hydroxide 作用下， 以 异丙醇 为溶剂， 反应 0.25h， 以99%的产率得到spiro[7α,12α-diacetoxy-5β-cholan-24-oic acid-3,6'-(3',3'-dimethyl-1',2',4',5'-tetraoxacyclohexane)]
  参考文献：
  名称：

  Mixed tetraoxanes containing the acetone subunit as antimalarials

  摘要：

  Eleven new tetraoxanes possessing cholic acid-derived carrier and isopropylidene moiety were synthesized and were tested in vitro and in vivo. In vitro screening revealed that nine of them were more potent against CQ-resistant W2 than CQ-susceptible D6 strain and that two of them were equally or more potent than artemisinin and mefloquine against multi- drug resistant TM91C235 strain. Amine 8 cured all mice at the dose of 160 mg/kg/day, while the anilide 9 exhibited MCD <= 20 mg/kg/day. The diol 13 was most potent antiproliferative with GI(50), TGI, LC50 MG_MID 0.98 mu M, 3.80 mu M, 11.22 mu M, respectively. All tested compounds showed no toxic effects. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.017

文献信息

• Mixed tetraoxanes containing the acetone subunit as antimalarials
  作者：Dejan M. Opsenica、Nataša Terzić、Philip L. Smith、Youngsun Yang、Lalaine Anova、Kirsten S. Smith、Bogdan A. Šolaja

  DOI：10.1016/j.bmc.2008.05.017

  日期：2008.7

  Eleven new tetraoxanes possessing cholic acid-derived carrier and isopropylidene moiety were synthesized and were tested in vitro and in vivo. In vitro screening revealed that nine of them were more potent against CQ-resistant W2 than CQ-susceptible D6 strain and that two of them were equally or more potent than artemisinin and mefloquine against multi- drug resistant TM91C235 strain. Amine 8 cured all mice at the dose of 160 mg/kg/day, while the anilide 9 exhibited MCD <= 20 mg/kg/day. The diol 13 was most potent antiproliferative with GI(50), TGI, LC50 MG_MID 0.98 mu M, 3.80 mu M, 11.22 mu M, respectively. All tested compounds showed no toxic effects. (c) 2008 Elsevier Ltd. All rights reserved.