(11β,16β)-21-(acetyloxy)-9-fluoro-16-methyl-3,20-dioxo-11-[(trimethylsilyl)oxy]pregna-1,4-dien-17-yl (1R)-1-phenylethylcarbamate | 733766-14-8

• 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: (11β,16β)-21-(acetyloxy)-9-fluoro-16-methyl-3,20-dioxo-11-[(trimethylsilyl)oxy]pregna-1,4-dien-17-yl (1R)-1-phenylethylcarbamate
• 英文别名: [2-[(8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-10,13,16-trimethyl-3-oxo-17-[[(1R)-1-phenylethyl]carbamoyloxy]-11-trimethylsilyloxy-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
• CAS: 733766-14-8
• 化学式: C₃₆H₄₈FNO₇Si
• 分子量: 653.864
• InChiKey: ASLCYDHECRXEEO-OPEMDXGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.82
• 重原子数：
  46
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (11β,16β)-21-(acetyloxy)-9-fluoro-16-methyl-3,20-dioxo-11-[(trimethylsilyl)oxy]pregna-1,4-dien-17-yl (1R)-1-phenylethylcarbamate 在 盐酸 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 24.0h， 以20 mg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：

  Discovery of betamethasone 17α-carbamates as dissociated glucocorticoid receptor modulators in the rat

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2008.07.037
• 作为产物：
  描述：

  (11β,16β)-9-fluoro-17-hydroxy-16-methyl-3,20-dioxo-11-[(trimethylsilyl)oxy]pregna-1,4-dien-21-yl acetate 、 (R)-(+)-1-苯乙基异氰酸酯 在 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以67 mg的产率得到(11β,16β)-21-(acetyloxy)-9-fluoro-16-methyl-3,20-dioxo-11-[(trimethylsilyl)oxy]pregna-1,4-dien-17-yl (1R)-1-phenylethylcarbamate
  参考文献：
  名称：

  Discovery of betamethasone 17α-carbamates as dissociated glucocorticoid receptor modulators in the rat

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2008.07.037