methylthiomethyl 11β,17α-dihydroxy-3-oxo-androst-4-ene-17β-carboxylate | 84099-87-6

• 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
• 英文名称: methylthiomethyl 11β,17α-dihydroxy-3-oxo-androst-4-ene-17β-carboxylate
• 英文别名: methylthiomethyl 11β,17α-dihydroxyandrost-4-en-3-one-17β-carboxylate；methylsulfanylmethyl (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17-carboxylate
• CAS: 84099-87-6
• 化学式: C₂₂H₃₂O₅S
• 分子量: 408.559
• InChiKey: ZGNJPNZWKAVCPY-DCJXKKNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methylthiomethyl 11β,17α-dihydroxy-3-oxo-androst-4-ene-17β-carboxylate 在 三氟乙酸酐 作用下， 以 吡啶 为溶剂， 生成 methylthiomethyl 17α-hydroxy-11β-trifluoroacetoxyandrost-4-en-3-one-17β-carboxylate
  参考文献：
  名称：

  Soft steroids having anti-inflammatory activity

  摘要：

  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。

  公开号：

  US04710495A1
• 作为产物：
  描述：

  氢化可的松 在 sodium periodate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 2.5h， 生成 methylthiomethyl 11β,17α-dihydroxy-3-oxo-androst-4-ene-17β-carboxylate
  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

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
• US4710495A
  申请人：——

  公开号：US4710495A

  公开（公告）日：1987-12-01
• US4996335A
  申请人：——

  公开号：US4996335A

  公开（公告）日：1991-02-26