6α,9α-difluoro-11β-hydroxy-16α,17α-isopropylidenedioxy-21-methanesulfonyloxy-pregna-1,4-diene-3,20-dione | 3793-01-9

• 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: 6α,9α-difluoro-11β-hydroxy-16α,17α-isopropylidenedioxy-21-methanesulfonyloxy-pregna-1,4-diene-3,20-dione
• 英文别名: 6α,9α-difluoro-11β-hydroxy-16α,17α-isopropylidenedioxy-21-methylsulfonyloxypregna-1,4-diene-3,20-dione；[2-[(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxoethyl] methanesulfonate
• CAS: 3793-01-9
• 化学式: C₂₅H₃₂F₂O₈S
• 分子量: 530.587
• InChiKey: GKSGRRRXVSIHEY-WWBHNZBCSA-N

物化性质

• 沸点：
  660.0±55.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6α,9α-difluoro-11β-hydroxy-16α,17α-isopropylidenedioxy-21-methanesulfonyloxy-pregna-1,4-diene-3,20-dione 在 sodium hydrogensulfide 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以87%的产率得到bis(6α,9α-difluoro-11β-hydroxy-16α,17α-isopropylidenedioxy-3,20-dioxopregna-1,4-diene-21-yl)sulfide
  参考文献：
  名称：

  Studies on topical antiinflammatory agents. II. Synthesis and vasoconstrictive activity of 21-substituted corticosteroids with sulfur-containing moieties.

  摘要：

  在寻找新型局部抗炎药物的过程中，制备并测试了多种含有硫元素的21-取代皮质类固醇在人体的血管收缩活性。结构-活性关系研究表明，将21-羟基基团用低级烷基硫基团替代可以增强活性。21-甲硫基（3Ad）和21-乙硫基（3Ae）化合物的活性比9α-氟-11β, 21-二羟基-16β-甲基-17α-戊酸氧基-1, 4-孕甾二烯-3, 20-二酮（倍他米松17-戊酸酯，BV）更强。

  DOI：

  10.1248/cpb.37.1795
• 作为产物：
  描述：

  醋酸氟轻松 以99%的产率得到
  参考文献：
  名称：

  MITSUKUCHI, MORIHIRO;IKEMOTO, TOMOYUKI;TAGUCHI, MINORU;HIGUCHI, SHOHEI;AB+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 1795-1801

  摘要：

  DOI：

文献信息

• Novel glucocorticoid antedrugs possessing a 21-(γ-lactone) ring
  作者：Richard M. Angell、Keith Biggadike、Rosanne M. Farrell、Stephen S. Flack、Ashley P. Hancock、Wendy R. Irving、Sean M. Lynn、Panayiotis A. Procopiou

  DOI：10.1039/b200190j

  日期：2002.3.8

  A series of novel pregnane derivatives bearing γ-butyrolactones at C21 were prepared and tested as glucocorticoid agonists. The compounds were also tested for their lability in human plasma, and found to be rapidly hydrolysed by the enzyme paraoxonase to the respective hydroxyacids.

  一系列新型的孕烷衍生物，其在C21位带有γ-丁内酯结构，被制备并测试作为糖皮质激素激动剂。同时，这些化合物也在人体血浆中进行了稳定性测试，并发现它们能被酶对氧磷酶迅速水解为其各自的羟酸。
• An Extremely Powerful Acylation Reaction of Alcohols with Acid Anhydrides Catalyzed by Trimethylsilyl Trifluoromethanesulfonate
  作者：Panayiotis A. Procopiou、Simon P. D. Baugh、Stephen S. Flack、Graham G. A. Inglis

  DOI：10.1021/jo980011z

  日期：1998.4.1

  Trimethylsilyl trifluoromethanesulfonate is an excellent catalyst for the acylation of alcohols with acid anhydrides. Highly functionalized primary, secondary, tertiary, and allylic alcohols, and phenols, were acylated cleanly and efficiently and in a fraction of the time used under the standard DMAP conditions.
• Selective Plasma Hydrolysis of Glucocorticoid γ-Lactones and Cyclic Carbonates by the Enzyme Paraoxonase: An Ideal Plasma Inactivation Mechanism
  作者：Keith Biggadike、Richard M. Angell、Colin M. Burgess、Rosanne M. Farrell、Ashley P. Hancock、Andy J. Harker、Wendy R. Irving、Chris Ioannou、Panayiotis A. Procopiou、Rupert E. Shaw、Yemisi E. Solanke、Onkar M. P. Singh、Michael A. Snowden、Rob J. Stubbs、Sarah Walton、Helen E. Weston

  DOI：10.1021/jm990436t

  日期：2000.1.1
• MIKUTI, MORIKIMI;IKOMOTO, TOMOYUKI;VATANABEH, JOSIAKI;SODA, KAORU
  作者：MIKUTI, MORIKIMI、IKOMOTO, TOMOYUKI、VATANABEH, JOSIAKI、SODA, KAORU

  DOI：——

  日期：——
• 21-(2-OXO-TETRAHYDROFURAN)-THIO PREGNANE DERIVATIVES, A PROCESS FOR THEIR PRODUCTION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：GLAXO GROUP LIMITED

  公开号：EP0876393B1

  公开（公告）日：2000-07-05