9-fluoro-11β,21-dihydroxypregna-1,4,16-triene-3,20-dione | 61618-63-1

• 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: 9-fluoro-11β,21-dihydroxypregna-1,4,16-triene-3,20-dione
• 英文别名: Desoxymetasone Impurity A；(8S,9R,10S,11S,13S,14S)-9-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,11,12,14,15-hexahydro-6H-cyclopenta[a]phenanthren-3-one
• CAS: 61618-63-1
• 化学式: C₂₁H₂₅FO₄
• 分子量: 360.426
• InChiKey: UAEUTSQWOUBCLN-XRYUJSLGSA-N

物化性质

• 沸点：
  536.2±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（轻微）、甲醇（轻微、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-fluoro-11β,21-dihydroxypregna-1,4,16-triene-3,20-dione 在 lithium chloride 作用下， 以 吡啶 、 N-甲基乙酰胺 为溶剂， 生成 21-chloro-9-fluoro-11β-hydroxy-pregna-1,4,16-triene-3,20-dione
  参考文献：
  名称：

  Steroidal[16.alpha.,17-b]benzodioxins

  摘要：

  具有以下化学式的类固醇可以用作抗炎药物：其中R.sub.1为氢、酰氧基、卤素或1至10个碳原子的烷氧基；R.sub.2为卤素或氰基；R.sub.3为氢或卤素；R.sub.4为羰基、β-羟甲基或β-乙酰氧甲基；R.sub.5为氢或氟。

  公开号：

  US04113722A1
• 作为产物：
  描述：

  21-乙酰氧基-9-氟-11-羟基孕甾-1,4,16-三烯-3,20-酮 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 9-fluoro-11β,21-dihydroxypregna-1,4,16-triene-3,20-dione
  参考文献：
  名称：

  Khalil, Mounir A.; Maponya, Mamakiri F.; Ko, Dong-Hoon, Medicinal Chemistry Research, 1996, vol. 6, # 1, p. 52 - 60

  摘要：

  DOI：

文献信息

• Steroidal[16.alpha.,17-b]benzodioxins
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04113722A1

  公开（公告）日：1978-09-12

  Steroids having the formula ##STR1## wherein R.sub.1 is hydrogen, acyloxy, halogen or alkoxy of 1 to 10 carbons; R.sub.2 is halogen or cyano; R.sub.3 is hydrogen or halogen; R.sub.4 is carbonyl, .beta.-hydroxymethylene or .beta.-acetyloxymethylene; and R.sub.5 is hydrogen or fluorine; can be used as antiinflammatory agents.

  具有以下化学式的类固醇可以用作抗炎药物：其中R.sub.1为氢、酰氧基、卤素或1至10个碳原子的烷氧基；R.sub.2为卤素或氰基；R.sub.3为氢或卤素；R.sub.4为羰基、β-羟甲基或β-乙酰氧甲基；R.sub.5为氢或氟。
• Steroidal (16.alpha.,17-d)cyclohexenes
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US03944584A1

  公开（公告）日：1976-03-16

  A series of novel steroidal[ 16.alpha., 17-d]cyclohexenes having a 9-fluoro group is disclosed herein for use as anti-inflammatory agents.

  本文披露了一系列具有9-氟基的新型类固醇[16.alpha.，17-d]环己烯，用作抗炎药物。
• 16.alpha.-ARYLCARBONYLPREGNENES
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US03976638A1

  公开（公告）日：1976-08-24

  Topical and systemic anti-inflammatory activity is exhibited by steroids having the formula ##SPC1## And the 1,2-dehydro derivatives thereof, wherein R.sub.1 is phenyl, naphthyl, or substituted phenyl or naphthyl.

  具有以下式子##SPC1##和其1,2-去氢衍生物的类固醇表现出局部和全身抗炎活性，其中R.sub.1是苯基，萘基或取代苯基或萘基。
• New Steroidal Antiinflammatory Antedrugs: Steroidal [16.alpha.,17.alpha.-d]-3'-Carbethoxyisoxazolines
  作者：Taesoo Kwon、Ann S. Heiman、Ebenezer T. Oriaku、Kyoungjin Yoon、Henry J. Lee

  DOI：10.1021/jm00006a026

  日期：1995.3

  Novel steroidal antiinflammatory antedrugs, 11 beta,20-dihydroxy-3,20-dioxo-3'-(ethoxycarbonyl)-isoxazolino[16,17-d]pregna-1,4-diene (2a) and 9-fluoro-11 beta,20-dihydroxy-3,20-dioxo-3'-ethoxy-carbonylisoxazolino[16,17-d]pregna-1,4-diene (2b) were prepared in 97% yield via 1,3-dipolar cycloaddition of carbethoxyformonitrile (CEFNO) to 11 beta,21-dihydroxy-3,20-dioxopregna-1,4,16-triene (1a) and 11 beta,21-dihydroxy-3,20-dioxo-9-fluoropregna-1,4,16-triene(1b), respectively, which were prepared via five steps from prednisolone and 9-fluoroprednisolone, respectively. The treatment of steroids 2a and 2b with acetic anhydride in pyridine led to the corresponding 21-acetates 3a and 3b, respectively, in 95% yield. Dose-response profiles of the croton oil-induced ear edema bioassay in rats were used to calculate the following ID50 values (nmol/ear resulting in a 50% reduction of edema): prednisolone (P), 540 nmol; 2b, 135 nmol; and 3b, 101 nmol. Inhibition of edema did not exceed 50% following application of either 2a or 3a. Relative potency calculations indicated that 2b was 4-fold and 3b 5.3-fold more potent than the parent compound P when applied topically. No significant adverse systemic effects were seen following treatments with 3b. These results suggest that C-9-fluorination, side-chain hydroxy group esterification, and [16 alpha,17 alpha-d]-3'-carbethoxyisoxazoline additions to the conventional steroid P improve topical antiinflammatory activity without concomitant increases in adverse systemic activity.
• US3944584A
  申请人：——

  公开号：US3944584A

  公开（公告）日：1976-03-16