11β,17β-dihydroxy-21-methyl-17α-pregna-1,4,6-trien-20-yn-3-one | 74915-58-5

• 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,17β-dihydroxy-21-methyl-17α-pregna-1,4,6-trien-20-yn-3-one
• 英文别名: 11β,17β-dihydroxy-17α-(1-propynyl)androst-1,4,6-trien-3-one；11β,17β-dihydroxy-17-(1-propynyl)1,4,6-androstatrien-3-one；RU26988；(8S,9S,10R,11S,13S,14S,17S)-11,17-dihydroxy-10,13-dimethyl-17-prop-1-ynyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthren-3-one
• CAS: 74915-58-5
• 化学式: C₂₂H₂₆O₃
• 分子量: 338.447
• InChiKey: IXJKSIRTUSUXQC-ZXYIWLIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-丙炔溴化镁 、 3-ethoxy-11β-hydroxy-3,5-androstadien-17-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 11β,17β-dihydroxy-21-methyl-17α-pregna-1,4,6-trien-20-yn-3-one
  参考文献：
  名称：

  17α-Alkynyl-11β,17-dihydroxyandrostane derivatives : A new class of potent glucocorticoids.

  摘要：

  Replacement of the characteristic dihydroxyacetone side chain of corticoids by a 17 alpha-alkynyl-17 beta-hydroxy moiety was investigated. It was found that, in particular, the 17 alpha-propynyl substitution is favorable for high local anti-inflammatory activity with reduced systemic effects. Moreover, these compounds were found to be devoid of any affinity for the aldosterone receptor, and may thus be considered as pure glucocorticoids.

  DOI：

  10.1016/0039-128x(81)90084-2

文献信息

• 17α-Alkynyl-11β,17-dihydroxyandrostane derivatives : A new class of potent glucocorticoids.
  作者：G. Teutsch、G. Costerousse、R. Deraedt、J. Benzoni、M. Fortin、D. Philibert

  DOI：10.1016/0039-128x(81)90084-2

  日期：1981.12

  Replacement of the characteristic dihydroxyacetone side chain of corticoids by a 17 alpha-alkynyl-17 beta-hydroxy moiety was investigated. It was found that, in particular, the 17 alpha-propynyl substitution is favorable for high local anti-inflammatory activity with reduced systemic effects. Moreover, these compounds were found to be devoid of any affinity for the aldosterone receptor, and may thus be considered as pure glucocorticoids.