(8S,9S,10R,11S,13S,14S,17R)-17-[2-[(4,5-dimethyl-1,3-thiazol-2-yl)sulfanyl]acetyl]-11,17-dihydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one | 1168140-62-2

• 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)-17-[2-[(4,5-dimethyl-1,3-thiazol-2-yl)sulfanyl]acetyl]-11,17-dihydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 1168140-62-2
• 化学式: C₂₆H₃₅NO₄S₂
• 分子量: 489.7
• InChiKey: OWZZHTDHOMLCGR-OKKNSTDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  呋喃甲酰氯 、 (8S,9S,10R,11S,13S,14S,17R)-17-[2-[(4,5-dimethyl-1,3-thiazol-2-yl)sulfanyl]acetyl]-11,17-dihydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-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)-17-[2-[(4,5-dimethyl-1,3-thiazol-2-yl)sulfanyl]acetyl]-11-hydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-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：

  2,4,5-三甲基噻唑 、 11beta,17,21-三羟基孕甾-4-烯-3,20-二酮 21-甲烷磺酸酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 (8S,9S,10R,11S,13S,14S,17R)-17-[2-[(4,5-dimethyl-1,3-thiazol-2-yl)sulfanyl]acetyl]-11,17-dihydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-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

文献信息

• Steroidal C-21 mercapto derivatives as dissociated steroids: Discovery of an inhaled dissociated steroid
  作者：Purakkattle Biju、Kevin McCormick、Robert Aslanian、Michael Berlin、Daniel Solomon、Richard Chapman、Robbie McLeod、Daniel Prelusky、Stephen Eckel、George Kelly、Michelle Natiello、Aileen House、Xiomara Fernandez、Rema Bitar、Jonathan Phillips、John Anthes

  DOI：10.1016/j.bmcl.2011.08.108

  日期：2011.11

  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.