(3S,5S,8S,9S,10R,13S,14S,17S)-17-((4R,5R)-5-isopentyl-2,2,4-trimethyl-1,3-dioxolan-4-yl)-10,13-dimethyl-6-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl methanesulfonate | 1151467-54-7

• 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: (3S,5S,8S,9S,10R,13S,14S,17S)-17-((4R,5R)-5-isopentyl-2,2,4-trimethyl-1,3-dioxolan-4-yl)-10,13-dimethyl-6-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl methanesulfonate
• CAS: 1151467-54-7
• 化学式: C₃₁H₅₂O₆S
• 分子量: 552.816
• InChiKey: IZHKLCOWDQGQSH-CQXGVUOPSA-N

物化性质

• 沸点：
  625.5±55.0 °C(predicted)
• 密度：
  1.14±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3S,5S,8S,9S,10R,13S,14S,17S)-17-((4R,5R)-5-isopentyl-2,2,4-trimethyl-1,3-dioxolan-4-yl)-10,13-dimethyl-6-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl methanesulfonate 在 lithium carbonate 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以0.95 g的产率得到(20R,22R)-20,22-isopropylidenedioxy-5α-cholest-2-en-6-one
  参考文献：
  名称：

  Synthesis of ponasterone A derivatives with various steroid skeleton moieties and evaluation of their binding to the ecdysone receptor of Kc cells

  摘要：

  A series of ponasterone A (PNA) derivatives with various steroid moieties were synthesized to measure their binding activity to the ecdysone receptors of Drosophila Kc cells. The activity of compounds was evaluated by deter-mining the concentration required to give the 50% inhibition (IC50 in M) of the incorporation of [H-3]PNA to Drosophila Kc cells. Compounds with no functional groups such as OH and C=O group in the steroid skeleton moiety were inactive. By the introduction of functional groups such as the OH and the C=O group in the steroidal structure, these compounds became active. Some compounds containing the A/B-trans ring fusion, which is different from that (A/B-cis) of ecdysteroids were also active. The oxidation of CH2 at 6-position to C=O, enhanced the activity 19 times, but the activity was erased by the reduction of oxo to OH group at 6-position. The activity was enhanced about 250 times by the conversion of A/B ring configuration from trans [(20R,22R)-2 beta,3 beta,20,22-tetrahydroxy-5 alpha-cholestan-6-one: pIC(50) = 4.84] to cis [(20R,22R)-2 beta,3 beta,20,22-tetrahydroxy-5 beta-cholestan-6-one: pIC(50) = 7.23]. The latter cis-type compound which is the most potent among compounds synthesized in this study was equipotent to the natural molting hormone, 20-hydroxyecdysone, even though it is 1/50 of PNA. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.08.005
• 作为产物：
  描述：

  (20R,22R)-3β-hydroxy-20,22-isopropylidenedioxy-5α-cholestan-6-one 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以2.26 g的产率得到(3S,5S,8S,9S,10R,13S,14S,17S)-17-((4R,5R)-5-isopentyl-2,2,4-trimethyl-1,3-dioxolan-4-yl)-10,13-dimethyl-6-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl methanesulfonate
  参考文献：
  名称：

  Synthesis of ponasterone A derivatives with various steroid skeleton moieties and evaluation of their binding to the ecdysone receptor of Kc cells

  摘要：

  A series of ponasterone A (PNA) derivatives with various steroid moieties were synthesized to measure their binding activity to the ecdysone receptors of Drosophila Kc cells. The activity of compounds was evaluated by deter-mining the concentration required to give the 50% inhibition (IC50 in M) of the incorporation of [H-3]PNA to Drosophila Kc cells. Compounds with no functional groups such as OH and C=O group in the steroid skeleton moiety were inactive. By the introduction of functional groups such as the OH and the C=O group in the steroidal structure, these compounds became active. Some compounds containing the A/B-trans ring fusion, which is different from that (A/B-cis) of ecdysteroids were also active. The oxidation of CH2 at 6-position to C=O, enhanced the activity 19 times, but the activity was erased by the reduction of oxo to OH group at 6-position. The activity was enhanced about 250 times by the conversion of A/B ring configuration from trans [(20R,22R)-2 beta,3 beta,20,22-tetrahydroxy-5 alpha-cholestan-6-one: pIC(50) = 4.84] to cis [(20R,22R)-2 beta,3 beta,20,22-tetrahydroxy-5 beta-cholestan-6-one: pIC(50) = 7.23]. The latter cis-type compound which is the most potent among compounds synthesized in this study was equipotent to the natural molting hormone, 20-hydroxyecdysone, even though it is 1/50 of PNA. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.08.005