(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-(isoquinolin-1-ylthio)acetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one | 1166867-05-5

• 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: (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-(isoquinolin-1-ylthio)acetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
• CAS: 1166867-05-5
• 化学式: C₃₀H₃₃NO₄S
• 分子量: 503.662
• InChiKey: STSCYLYWQVGZQG-DISMZPNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  36.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.49
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  呋喃甲酰氯 、 (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-(isoquinolin-1-ylthio)acetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 [(8S,9S,10R,11S,13S,14S,17R)-11-hydroxy-17-(2-isoquinolin-1-ylsulfanylacetyl)-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl] furan-2-carboxylate
  参考文献：
  名称：

  Steroidal C-21 mercapto derivatives as dissociated steroids: Discovery of an inhaled dissociated steroid

  摘要：

  A series of C-21 mercapto derivatives of hydrocortisone have been synthesized and evaluated in cell based transrepression and transactivation assays. The benzothiazole derivative, compound 6 not only showed a dissociated profile in vitro functional assays but also a pharmacological profile in a Brown-Norway rat therapeutic index model of asthma that dissociated side effects (thymolysis) while maintaining efficacy against pulmonary inflammation and lung function. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.108
• 作为产物：
  描述：

  泼尼松龙 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-(isoquinolin-1-ylthio)acetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
  参考文献：
  名称：

  Steroidal C-21 mercapto derivatives as dissociated steroids: Discovery of an inhaled dissociated steroid

  摘要：

  A series of C-21 mercapto derivatives of hydrocortisone have been synthesized and evaluated in cell based transrepression and transactivation assays. The benzothiazole derivative, compound 6 not only showed a dissociated profile in vitro functional assays but also a pharmacological profile in a Brown-Norway rat therapeutic index model of asthma that dissociated side effects (thymolysis) while maintaining efficacy against pulmonary inflammation and lung function. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.108