11β-hydroxy-17α-methoxy-3-oxoandrost-4-ene 17β-carboxylic acid, chloromethyl ester | 115841-20-8

• 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-hydroxy-17α-methoxy-3-oxoandrost-4-ene 17β-carboxylic acid, chloromethyl ester
• 英文别名: chloromethyl 17α-methoxy-11β-hydroxyandrost-4-en-3-one-17β-carboxylate；chloromethyl (8S,9S,10R,11S,13S,14S,17R)-11-hydroxy-17-methoxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17-carboxylate
• CAS: 115841-20-8
• 化学式: C₂₂H₃₁ClO₅
• 分子量: 410.938
• InChiKey: JYIVZEBLHAWFFG-DCJXKKNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  11β-hydroxy-17α-methoxy-3-oxoandrost-4-ene 17β-carboxylic acid, chloromethyl ester 生成 17α-ethoxy-11β-hydroxy-3-oxoandrost-4-ene 17β-carboxylic acid, chloromethyl ester
  参考文献：
  名称：

  BODOR, NICHOLAS S.

  摘要：

  DOI：
• 作为产物：
  描述：

  11β-hydroxy-17α-methoxy-3-oxoandrost-4-ene 17β-carboxylic acid methyl ester 在 potassium tert-butylate 、 四丁基硫酸氢铵 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 1.5h， 生成 11β-hydroxy-17α-methoxy-3-oxoandrost-4-ene 17β-carboxylic acid, chloromethyl ester
  参考文献：
  名称：

  Regioselective O-alkylation of cortienic acid and synthesis of a new class of glucocorticoids containing a 17α-alkoxy, a 17α-(1′-alkoxyethyloxy), a 17α-alkoxymethyloxy, or a 17α-methylthiomethyloxy function

  摘要：

  The synthesis of a new class of glucocorticoids, to be evaluated as anti-inflammatory agents with expected low systemic toxicity, is described. The new steroids possess a 17-beta-chloromethyl carboxylate function and a 17-alpha-alkoxy, a 17-alpha-(1'-alkoxyethyloxy), a 17-alpha-alkoxymethyloxy, or a 17-alpha-methylthiomethyloxy function. A 17-alpha-alkoxy function is a new feature in cortisol analogs.

  DOI：

  10.1016/0039-128x(91)90008-j

文献信息

• Soft steroids having anti-inflammatory activity
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US04710495A1

  公开（公告）日：1987-12-01

  Novel soft steroid anti-inflammatory agents, said agents being esters or thioesters of 17.alpha.-alkoxy-11.beta.-hydroxyandrost-4-en-3-one-17.beta.-carboxylic acids, pharmaceutical compositions containing said agents, novel chemical intermediates useful in the preparation of said agents and methods of administering same to mammals in the treatment of inflammation. Preferred compounds are the haloalkyl esters of 17.alpha.-alkoxy-11.beta.-hydroxyandrost-4-en-3-one-17.beta.-carboxylic acids.

  一种新型软性类固醇抗炎剂，该剂为17α-烷氧基-11β-羟基雄甾-4-烯-3-酮-17β-羧酸酯或硫酯，含有该剂的制药组合物，用于制备该剂的新型化学中间体以及在治疗炎症中向哺乳动物施用该剂的方法。优选的化合物是17α-烷氧基-11β-羟基雄甾-4-烯-3-酮-17β-羧酸的卤代烷基酯。
• SOFT STEROIDS HAVING ANTI-INFLAMMATORY ACTIVITY
  申请人：BODOR, Nicholas S.

  公开号：EP0334853B1

  公开（公告）日：1993-06-09
• EP0334853A4
  申请人：——

  公开号：EP0334853A4

  公开（公告）日：1990-02-26
• ENHANCEMENT OF ACTIVITY AND/OR DURATION OF ACTION OF SELECTED ANTI-INFLAMMATORY STEROIDS
  申请人：BODOR, Nicholas S.

  公开号：EP1658083B1

  公开（公告）日：2007-08-08
• Enhancement of activity and/or duration of action of selected anti-inflammatory steroids for topical or other local application
  申请人：Bodor S. Nicholas

  公开号：US20050020551A1

  公开（公告）日：2005-01-27

  Methods and compositions for enhancing the activity and/or duration of action of soft anti-inflammatory steroids of the haloalkyl 17α-alkoxy-11β-hydroxyandrost-4-en-3-one-17β-carboxylate type and the corresponding Δ 1,4 compounds and of anti-inflammatory steroids of the hydrocortisone and prednisolone type are described. The enhancing agents have the formula: wherein R is H or C 1 -C 4 alkyl; Z 1 is carbonyl or β-hydroxymethylene; X 1 is —O— or —S—; R 5 is —OH, —OR 6 , —OCOOR 6 or —OCOR 7 wherein R 6 is C 1 -C 4 alkyl and R 7 is C 1 -C 4 alkyl, fluoromethyl or chloromethyl; and the dotted line in ring A indicates that the 1,2-linkage is saturated or unsaturated; with the proviso that when R is C 1 -C 4 alkyl, then R 5 is —OH.