(11beta,16beta)-9-Fluoro-11,21-dihydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl (1R)-1-phenylethylcarbamate | 733765-76-9

• 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: (11beta,16beta)-9-Fluoro-11,21-dihydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl (1R)-1-phenylethylcarbamate
• 英文别名: [(8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] N-[(1R)-1-phenylethyl]carbamate
• CAS: 733765-76-9
• 化学式: C₃₁H₃₈FNO₆
• 分子量: 539.644
• InChiKey: BLPNJKOYOIDEJJ-GROVHKIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (11beta,16beta)-21-(acetyloxy)-9-fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl (1R)-1-phenylethylcarbamate 在 乙酸乙酯 、 水 、 Brine 、 Sodium sulfate-III 、 silica gel 、 Hexane ethyl acetate dichloromethane methanol 作用下， 以 pre-mixed solution 、 chloroform methanol 为溶剂， 反应 24.5h， 以to yield 20 mg of (11β,16β)-9-fluoro-11,21-dihydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl (1R)-1-phenylethylcarbamate as a white solid的产率得到(11beta,16beta)-9-Fluoro-11,21-dihydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl (1R)-1-phenylethylcarbamate
  参考文献：
  名称：

  17-carbamoyloxy cortisol derivatives as selective glucocorticoid receptor modulators

  摘要：

  本发明涵盖了I式化合物或其药学上可接受的盐或水合物，其可用作选择性糖皮质激素受体配体，用于治疗各种自身免疫和炎症性疾病或病况。还包括药物组合物和使用方法。

  公开号：

  US07732432B2

文献信息

• Discovery of betamethasone 17α-carbamates as dissociated glucocorticoid receptor modulators in the rat
  作者：Amjad Ali、James M. Balkovec、Mark Greenlee、Milton L. Hammond、Greg Rouen、Gayle Taylor、Monica Einstein、Lan Ge、Georgianna Harris、Terri M. Kelly、Paul Mazur、Shilpa Pandit、Joseph Santoro、Ayesha Sitlani、Chuanlin Wang、Joann Williamson、Michael J. Forrest、Ester Carballo-Jane、Silvi Luell、Karen Lowitz、Denise Visco

  DOI：10.1016/j.bmc.2008.07.037

  日期：2008.8

  A series of betamethasone 17 alpha-carbamates were designed, synthesized, and evaluated for their ability to dissociate the two main functions of the glucocorticoid receptor, that is, transactivation and transrepression, in rat cell lines. A number of alkyl substituted betamethasone 17 alpha-carbamates were identified with excellent affinity for the glucocorticoid receptor (e.g., 7, GR IC(50) 5.1 nM) and indicated dissociated profiles in functional assays of transactivation (rat tyrosine aminotransferase, TAT, and rat glutamine synthetase, GS) and transrepression (human A549 cells, MMP-1 assay). Gratifyingly, the in-vivo profile of these compounds, for example, 7, also indicated potent anti-inflammatory activity with impaired effects on glucose, insulin, triglycerides, and body weight. Taken together, these results indicate that dissociated glucocorticoid receptor modulators can be identified in rodents. (C) 2008 Published by Elsevier Ltd.
• US7732432B2
  申请人：——

  公开号：US7732432B2

  公开（公告）日：2010-06-08