氟替卡松杂质 | 192191-49-4

• 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
• 中文名称: 氟替卡松杂质
• 英文名称: S-fluoromethyl 6α-fluoro-9β,11β-epoxy-16α-methyl-17α-propionyloxy-3-oxoandrosta-1,4-diene-17β-carbothioate
• 英文别名: [(1S,2S,8S,10S,11S,13R,14R,15S,17S)-8-fluoro-14-(fluoromethylsulfanylcarbonyl)-2,13,15-trimethyl-5-oxo-18-oxapentacyclo[8.8.0.01,17.02,7.011,15]octadeca-3,6-dien-14-yl] propanoate
• CAS: 192191-49-4
• 化学式: C₂₅H₃₀F₂O₅S
• 分子量: 480.573
• InChiKey: RTFLONJEADIYNT-ZDWTZTIGSA-N

物化性质

• 沸点：
  562.6±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  98.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  氟替卡松杂质 在 氢氟酸 作用下， 以 水 为溶剂， 反应 7.0h， 生成 氟替卡松丙酸酯
  参考文献：
  名称：

  [EN] 17.BETA- (ALPHA-HYDROXY) -ESTERS OF ANDROSTANES AS INTERMEDIATES FOR THE PREPARATION FOR THE PREPARATION OF 17.BETA.-FLUORINATED-ANDROSTANE ESTERS
  [FR] ESTERS DE 17-BETA-(ALPHA-HYDROXY) D'ANTROSTANES, UTILISES COMME INTERMEDIAIRES DANS LA PREPARATION D'ESTERS D'ANDROSTANE 15-BETA FLUORES.

  摘要：

  通过形成新的雄甾烷S-羟基烷基或芳基-17-羰硫酸酯中间体，制备多卤代类固醇，特别是雄甾烷氟衍生物皮质类固醇的方法。

  公开号：

  WO2004052912A1
• 作为产物：
  描述：

  (6α,9β,11β,16α,17α)-9,11-epoxy-6-fluoro-17-hydroxy-16-methyl-3-oxo-androsta-1,4-diene-17-carboxylic acid 在 硫化氢 、 potassium carbonate 、 二乙胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.92h， 生成 氟替卡松杂质
  参考文献：
  名称：

  Automated radiosynthesis of no-carrier-added [S-fluoromethyl- 18F]fluticasone propionate as a radiotracer for lung deposition studies with PET

  摘要：

  Fluticasone propionate [(S)-fluoromethyl-6 alpha,9 alpha-difluoro-11 beta-hydroxy-16 alpha-methyl-3-oxo-17 alpha-(propionyloxy)-androsta-1,4-diene-17 beta-carbothioate; FP] is a potent anti-inflammatory steroid with several therapeutic indications, including use as an anti-asthmatic drug when administered as sized particles by inhalation from a pressurised metered-dose inhaler (pMDI). FP was successfully labelled with fluorine-18 (t(1/2) = 109.6 min; beta(+) = 100%) by displacement of tosylate with cyclotron-produced no-carrier-added [F-18]fluoride in an (S)-tosylmethyl precursor prepared from the known (S)-chloromethyl analogue of FP. Radiochemically pure [S-fluoromethyl-F-18]FP was separated by reverse phase HPLC in 35% radiochemical yield (decay-corrected) within 80 min form the end of radionuclide production (as verified by, radio-HPLC, LC-MS and LC-NMR). The radiosynthesis was automated for the safe production of high radioactivities (20-50 mCi) of [F-18]FP in a lead-shielded hot-cell for subsequent incorporation into formulated FP particles within a pMDI and subsequent study of FP deposition in human lung using positron emission tomography (PET).

  DOI：

  10.1002/(sici)1099-1344(199707)39:7<567::aid-jlcr999>3.0.co;2-p

文献信息

• 17.Beta-(alpha-hydroxy)-esters of androstanes as intermediates for the preparation of 17.beta-fluorinated-androstane esters
  申请人：Cainelli Adele Gianfranco

  公开号：US20060116359A1

  公开（公告）日：2006-06-01

  Process for the preparation of polyhalogenated steroids, in particular of androstanic fluoro derivatives corticosteroids by means of the formation of new androstanic S-hydroxy alkyl or aralkyl-17-carbothioate intermediates.

  通过形成新的雄甾烷 S-羟基烷基或芳烷基-17-硫代碳酸酯中间体，制备多卤代类固醇，特别是雄甾烷氟衍生物皮质类固醇的工艺。
• 17.BETA-[ALPHA-HYDROXY]-ESTERS OF ANDROSTANES AS INTERMEDIATES FOR THE PREPARATION OF 17.BETA.-FLUORINATED-ANDROSTANE ESTERS
  申请人：Farmabios S.p.A.

  公开号：EP1575983A1

  公开（公告）日：2005-09-21
• [EN] 17.BETA- (ALPHA-HYDROXY) -ESTERS OF ANDROSTANES AS INTERMEDIATES FOR THE PREPARATION FOR THE PREPARATION OF 17.BETA.-FLUORINATED-ANDROSTANE ESTERS<br/>[FR] ESTERS DE 17-BETA-(ALPHA-HYDROXY) D'ANTROSTANES, UTILISES COMME INTERMEDIAIRES DANS LA PREPARATION D'ESTERS D'ANDROSTANE 15-BETA FLUORES.
  申请人：FARMABIOS SRL

  公开号：WO2004052912A1

  公开（公告）日：2004-06-24

  Process for the preparation of polyhalogenated steroids, in particular of androstanic fluoro derivatives corticosteroids by means of the formation of new androstanic S-hydroxy alkyl or aralkyl-17-carbothioate intermediates.

  通过形成新的雄甾烷S-羟基烷基或芳基-17-羰硫酸酯中间体，制备多卤代类固醇，特别是雄甾烷氟衍生物皮质类固醇的方法。
• Automated radiosynthesis of no-carrier-added [S-fluoromethyl- 18F]fluticasone propionate as a radiotracer for lung deposition studies with PET
  作者：Franklin I. Aigbirhio、Richard M. Carr、Victor W. Pike、Colin J. Steel、Derek R. Sutherland

  DOI：10.1002/(sici)1099-1344(199707)39:7<567::aid-jlcr999>3.0.co;2-p

  日期：1997.7

  Fluticasone propionate [(S)-fluoromethyl-6 alpha,9 alpha-difluoro-11 beta-hydroxy-16 alpha-methyl-3-oxo-17 alpha-(propionyloxy)-androsta-1,4-diene-17 beta-carbothioate; FP] is a potent anti-inflammatory steroid with several therapeutic indications, including use as an anti-asthmatic drug when administered as sized particles by inhalation from a pressurised metered-dose inhaler (pMDI). FP was successfully labelled with fluorine-18 (t(1/2) = 109.6 min; beta(+) = 100%) by displacement of tosylate with cyclotron-produced no-carrier-added [F-18]fluoride in an (S)-tosylmethyl precursor prepared from the known (S)-chloromethyl analogue of FP. Radiochemically pure [S-fluoromethyl-F-18]FP was separated by reverse phase HPLC in 35% radiochemical yield (decay-corrected) within 80 min form the end of radionuclide production (as verified by, radio-HPLC, LC-MS and LC-NMR). The radiosynthesis was automated for the safe production of high radioactivities (20-50 mCi) of [F-18]FP in a lead-shielded hot-cell for subsequent incorporation into formulated FP particles within a pMDI and subsequent study of FP deposition in human lung using positron emission tomography (PET).