(6alpha,11beta,16alpha,17alpha)-6,9-二氟-11-羟基-16,17-[(1-甲基亚乙基)二(氧基)]-3,20-二氧代孕甾-1,4-二烯-21-酸 | 106931-78-6

• 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: (6alpha,11beta,16alpha,17alpha)-6,9-二氟-11-羟基-16,17-[(1-甲基亚乙基)二(氧基)]-3,20-二氧代孕甾-1,4-二烯-21-酸
• 英文名称: 21-oic acid of Fluocinolone Acetonide
• 英文别名: 6alpha,9-Difluoro-11beta-hydroxy-16alpha,17-(1-methylethylidenedioxy)-3,20-dioxopregna-1,4-dien-21-oic acid；2-[(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxoacetic acid
• CAS: 106931-78-6
• 化学式: C₂₄H₂₈F₂O₇
• 分子量: 466.479
• InChiKey: KUVGGCPFHYXHKI-BDQUCZKRSA-N

物化性质

• 熔点：
  >250oC (dec.)
• 沸点：
  584.1±50.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (6alpha,11beta,16alpha,17alpha)-6,9-二氟-11-羟基-16,17-[(1-甲基亚乙基)二(氧基)]-3,20-二氧代孕甾-1,4-二烯-21-酸 在 sodium hydroxide 、 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 生成 6α,9α-difluoro-11β-hydroxy-16α,17α-isopropylidenedioxy-17β-(methylthio)androsta-1,4-dien-3-one
  参考文献：
  名称：

  A concise access to a new class of selective anti-inflammatory steroid derivatives

  摘要：

  The 17 beta-thiomethyl-16 alpha,17 alpha-ketal motif of a new class of selective anti-inflammatory androstane derivatives useful in the treatment of asthma is readily constructed by a new radical degradation of the corticosteroid side chain. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10809-7
• 作为产物：
  描述：

  醋酸氟轻松 在 copper diacetate 、 间氯过氧苯甲酸 作用下， 反应 18.0h， 以70%的产率得到(6alpha,11beta,16alpha,17alpha)-6,9-二氟-11-羟基-16,17-[(1-甲基亚乙基)二(氧基)]-3,20-二氧代孕甾-1,4-二烯-21-酸
  参考文献：
  名称：

  摘要：

  Purpose. The soft drug approach was applied to the design of analogs of highly potent synthetic steroids but with a metabolically labile ester group which at the same time served as an activating group.Methods. Several structural modifications of soft antiinflammatory steroids were synthesized and tested in several assays of biological activity. The hydrolytic stability of the compounds was also determined.Results. One of the compounds synthesized was determined to be a very potent steroid and had a highly significant separation of topical from systemic activity. However, the compound demonstrated greater than expected stability in the hydrolysis studies.Conclusions. The goal of the soft drug approach has been achieved with the development of a highly potent drug which displays little or no systemic activity as measured in the tests presented here. The anticipated hydrolytic instability of the compounds was not corroborated, however, in view of other results, the interpretation is allowed that the rapid hydrolysis of the unbound fraction of the drug is an important factor in its lack of systemic effects.

  DOI：

  10.1023/a:1018907026460