20-二氢泼尼松龙酸 | 62358-12-7

• 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: 20-二氢泼尼松龙酸
• 英文名称: 11β,17α,20α-trihydroxy-3-oxo-1,4-pregnadien-21-oic acid
• 英文别名: 11β,17α,20-Trihydroxy-3-oxopregna-1,4-dien-21-oic acid；11β,17α,20-trihydroxy-3-oxopregn-1,4-diene-21-oic acid；11β,17α,20-Trihydroxy-3-oxopregn-1,4-dien-21-oic acid；20-dihydroprednisolonic acid；11β,17α,20-trihydroxy-3-oxo-1,4-pregnadiene-21-oic acid；11β,17,20β-trihydroxy-3-oxo-1,4-pregnadien-21-oic acid；2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-hydroxyacetic acid
• CAS: 62358-12-7
• 化学式: C₂₁H₂₈O₆
• 分子量: 376.45
• InChiKey: MABTYSTXQLOOCI-PEIJZJCNSA-N

物化性质

• 熔点：
  >213°C (dec.)
• 溶解度：
  二恶烷（轻微）、DMSO（轻微）、甲醇（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  20-二氢泼尼松龙酸 在 对甲苯磺酸 作用下， 以 乙醚 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 methyl 11β,17α,20α-trihydroxy-3-oxo-1,4-pregnadiene-21-oate 17,20-acetonide
  参考文献：
  名称：

  Effect of chirality at C-20 of methyl 11β,17α,20-trihydroxy-3-oxo-1,4-pregnadien-21-oate derivatives on antiinflammatory activity

  摘要：

  In an effort to determine the C-20 chirality effect on the antiinflammatory activity of 17beta-glycolate esters, methyl 11beta,17alpha,20-trihydroxy-3-oxo-1,4-pregnadien-21-oate and its 9alpha-fluoro analog, their acetonide and their carbonate derivatives were synthesized and evaluated. The agents were tested for their binding potency to the macrophage glucocorticoid receptor, and their effect on LPS-induced nitric oxide generation in RAW 264.7 cells. The acetonide derivatives showed the highest binding affinity while the triols and carbonates bound rather poorly to the receptors. With the exception of the triols, the a-isomer in each pair of the agents exhibited higher binding affinity to the receptor than its corresponding beta-isomer, clearly indicating that C-20 chirality has a significant effect on anti inflammatory activity. In addition, the alpha-isomers of the acetonides showed substantially higher binding affinity than the parent compound, prednisolone. In contrast to the high binding activity exhibited by some of the acetonides, all of the agents showed weak inhibitory effect on NO generation. Metabolic inactivation during assessment of NO inhibition may play it role in the divergence noted between receptor affinity and the measured biologic activity resulting from the binding. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00189-1
• 作为产物：
  描述：

  泼尼松龙 在 copper diacetate 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 49.0h， 生成 20-二氢泼尼松龙酸
  参考文献：
  名称：

  Effect of chirality at C-20 of methyl 11β,17α,20-trihydroxy-3-oxo-1,4-pregnadien-21-oate derivatives on antiinflammatory activity

  摘要：

  In an effort to determine the C-20 chirality effect on the antiinflammatory activity of 17beta-glycolate esters, methyl 11beta,17alpha,20-trihydroxy-3-oxo-1,4-pregnadien-21-oate and its 9alpha-fluoro analog, their acetonide and their carbonate derivatives were synthesized and evaluated. The agents were tested for their binding potency to the macrophage glucocorticoid receptor, and their effect on LPS-induced nitric oxide generation in RAW 264.7 cells. The acetonide derivatives showed the highest binding affinity while the triols and carbonates bound rather poorly to the receptors. With the exception of the triols, the a-isomer in each pair of the agents exhibited higher binding affinity to the receptor than its corresponding beta-isomer, clearly indicating that C-20 chirality has a significant effect on anti inflammatory activity. In addition, the alpha-isomers of the acetonides showed substantially higher binding affinity than the parent compound, prednisolone. In contrast to the high binding activity exhibited by some of the acetonides, all of the agents showed weak inhibitory effect on NO generation. Metabolic inactivation during assessment of NO inhibition may play it role in the divergence noted between receptor affinity and the measured biologic activity resulting from the binding. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00189-1

文献信息

• Anti-inflammatory carboxy pregnane derivatives
  申请人：Florida Agricultural and Mechanical University

  公开号：US04762919A1

  公开（公告）日：1988-08-09

  Compounds of the formula: ##STR1## wherein one X is COOR, CH.sub.2 COOR, CH(COOR).sub.2, CONHR, CH.sub.2 CONHR, or CN remaining X's are H, F, CH.sub.3, OH, COOR, CH.sub.2 COOR, CH(COOR).sub.2, CONHR, CH.sub.2 CONHR, or CN; Y is ##STR2## R is H, alkyl of 1-5 carbon atoms, or benzyl; R.sub.1 is CH.sub.2 OR.sub.3, COOR, or CONHR; R.sub.2 is H, OR.sub.3, or BR; R.sub.3 is H, COR.sub.4, or tetrahydropyranyl; R.sub.4 is alkyl of 1-5 carbon atoms or benzyl; R.sub.5 is H or COR.sub.4 ; represents a single or double bond; represents .alpha.-position, .beta.-position, or a mixture of .alpha.- and .beta.-positions; and --- represents .alpha.-position; and methods for preparing the same.

  该化合物的结构式为：##STR1## 其中一个X是COOR，CH.sub.2 COOR，CH(COOR).sub.2，CONHR，CH.sub.2 CONHR或CN，其余的X是H，F，CH.sub.3，OH，COOR，CH.sub.2 COOR，CH(COOR).sub.2，CONHR，CH.sub.2 CONHR或CN；Y是##STR2## R是H，1-5个碳原子的烷基或苄基；R.sub.1是CH.sub.2 OR.sub.3，COOR或CONHR；R.sub.2是H，OR.sub.3或BR；R.sub.3是H，COR.sub.4或四氢吡喃基；R.sub.4是1-5个碳原子的烷基或苄基；R.sub.5是H或COR.sub.4；代表单键或双键；代表α-位置、β-位置或α-和β-位置的混合；---代表α-位置；以及制备该化合物的方法。
• Organic Compounds with Reversible Red-Ox Potential as Oxidizers in Steroid Chemistry; I. Tetrazolium Salts
  作者：Maria A. Smoczkiewicz、Jan Jasiczak

  DOI：10.1055/s-1980-29195

  日期：——
• Oxidation of corticosteroids by flavins
  作者：J. Jasiczac、M.A. Smoczkiewicz

  DOI：10.1016/s0040-4039(00)98908-1

  日期：1985.1
• Organic Compounds with Reversible Red-Ox Potential as Oxidizing Agents in Steroid Chemistry; II¹. Indophenol Salts (Tillmans Reagent)
  作者：Jan Jasiczak、Maria A. Smoczkiewicz

  DOI：10.1055/s-1981-29603

  日期：——
• GLUCOCORTICOID CARBOXYLIC ACID ESTER FOR SUPPRESSION OF CUTANEOUS DELAYED HYPERSENSITIVITY
  申请人：THE ROCKEFELLER UNIVERSITY

  公开号：EP0317611A1

  公开（公告）日：1989-05-31