17α-butoxy-11β-hydroxy-3-oxoandrost-4-ene 17β-carboxylic acid, chloromethyl ester | 115841-48-0

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物
• 英文名称: 17α-butoxy-11β-hydroxy-3-oxoandrost-4-ene 17β-carboxylic acid, chloromethyl ester
• 英文别名: chloromethyl 11β-hydroxy-17α-butoxyandrost-4-en-3-one-17β-carboxylate；chloromethyl (8S,9S,10R,11S,13S,14S,17R)-17-butoxy-11-hydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17-carboxylate
• CAS: 115841-48-0
• 化学式: C₂₅H₃₇ClO₅
• 分子量: 453.019
• InChiKey: XYFCWZUCPBKRIX-KYUXFNSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl (8'S,9'S,10'R,11'S,13'S,14'S,17'R)-17'-butoxy-11'-hydroxy-10',13'-dimethylspiro[1,3-dioxolane-2,3'-2,4,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-17'-carboxylate 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 17α-butoxy-11β-hydroxy-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：BODOR, Nicholas S.

  公开号：EP0334853B1

  公开（公告）日：1993-06-09
• BODOR, NICHOLAS S.
  作者：BODOR, NICHOLAS S.

  DOI：——

  日期：——
• 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：EP1658083A1

  公开（公告）日：2006-05-24
• 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.