11β-hydroxy-17α-methylthiomethyloxy-3-oxoandrost-4-ene 17β-carboxylic acid, methyl ester | 115841-38-8

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物
• 英文名称: 11β-hydroxy-17α-methylthiomethyloxy-3-oxoandrost-4-ene 17β-carboxylic acid, methyl ester
• 英文别名: methyl 11β-hydroxy-17α-methylthiomethyloxyandrost-4-en-3-one-17β-carboxylate；methyl (8S,9S,10R,11S,13S,14S,17R)-11-hydroxy-10,13-dimethyl-17-(methylsulfanylmethoxy)-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17-carboxylate
• CAS: 115841-38-8
• 化学式: C₂₃H₃₄O₅S
• 分子量: 422.586
• InChiKey: DIWSGQQNTZKYFW-KJFLTHLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  98.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  11β-hydroxy-17α-methylthiomethyloxy-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-methylthiomethyloxy-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
• 作为产物：
  描述：

  17α-methylthiomethyloxy-3-oxo-11β-trifluoroacetoxyandrost-4-ene 17β-carboxylic acid, methyl ester 在 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 11β-hydroxy-17α-methylthiomethyloxy-3-oxoandrost-4-ene 17β-carboxylic acid, methyl 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
• US4710495A
  申请人：——

  公开号：US4710495A

  公开（公告）日：1987-12-01
• WO1989003390A1
  申请人：——

  公开号：WO1989003390A1

  公开（公告）日：1989-04-20