((6S,8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-6-yl)-acetic acid methyl ester | 65011-32-7

• 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: ((6S,8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-6-yl)-acetic acid methyl ester
• 英文别名: methyl 2-[(6S,8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-yl]acetate
• CAS: 65011-32-7
• 化学式: C₂₂H₃₂O₄
• 分子量: 360.494
• InChiKey: VZUAABWHJGHTDU-VBVQMDFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ((6S,8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-6-yl)-acetic acid methyl ester 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以79%的产率得到((6S,8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-6-yl)-acetic acid
  参考文献：
  名称：

  Design and synthesis of a new fluorescent probe for cytochrome P450 3A4 (CYP 3A4)

  摘要：

  Inhibition of CYP 3A4 catalytic activity is a principal mechanism for in vivo drug-drug interactions, sometimes leading to severe toxic effects. Rapid in vitro testing for CYP 3A4 high affinity/high inhibition potential has become part of the standard investigations for new drug candidates. Unfortunately, the complexity of the kinetics associated with CYP 3A4 catalyzed reactions (multiple substrates binding, non Michaelis-Menten kinetics) make these tests either inaccurate or tedious. We have designed and synthesized a new fluorescent probe, a testosterone substituted at the 6beta- position with a fluorescent deazaflavine moiety which is able to inhibit to the same extent the hydroxylation of compounds known to bind to different sites in the CYP 3A4 active site. Furthermore, the binding of this compound and its displacement from the active site can be followed by fluorescence measurements, which allows a rapid evaluation of the CYP 3A4 affinity of any new drug candidate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.027
• 作为产物：
  描述：

  睾酮 在 sodium chloride 、 palladium dichloride 、 lithium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 58.5h， 生成 ((6S,8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-6-yl)-acetic acid methyl ester
  参考文献：
  名称：

  Design and synthesis of a new fluorescent probe for cytochrome P450 3A4 (CYP 3A4)

  摘要：

  Inhibition of CYP 3A4 catalytic activity is a principal mechanism for in vivo drug-drug interactions, sometimes leading to severe toxic effects. Rapid in vitro testing for CYP 3A4 high affinity/high inhibition potential has become part of the standard investigations for new drug candidates. Unfortunately, the complexity of the kinetics associated with CYP 3A4 catalyzed reactions (multiple substrates binding, non Michaelis-Menten kinetics) make these tests either inaccurate or tedious. We have designed and synthesized a new fluorescent probe, a testosterone substituted at the 6beta- position with a fluorescent deazaflavine moiety which is able to inhibit to the same extent the hydroxylation of compounds known to bind to different sites in the CYP 3A4 active site. Furthermore, the binding of this compound and its displacement from the active site can be followed by fluorescence measurements, which allows a rapid evaluation of the CYP 3A4 affinity of any new drug candidate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.027

文献信息

• Design and synthesis of a new fluorescent probe for cytochrome P450 3A4 (CYP 3A4)
  作者：Antoinette Chougnet、Catherine Stoessel、Wolf-D. Woggon

  DOI：10.1016/j.bmcl.2003.08.027

  日期：2003.11

  Inhibition of CYP 3A4 catalytic activity is a principal mechanism for in vivo drug-drug interactions, sometimes leading to severe toxic effects. Rapid in vitro testing for CYP 3A4 high affinity/high inhibition potential has become part of the standard investigations for new drug candidates. Unfortunately, the complexity of the kinetics associated with CYP 3A4 catalyzed reactions (multiple substrates binding, non Michaelis-Menten kinetics) make these tests either inaccurate or tedious. We have designed and synthesized a new fluorescent probe, a testosterone substituted at the 6beta- position with a fluorescent deazaflavine moiety which is able to inhibit to the same extent the hydroxylation of compounds known to bind to different sites in the CYP 3A4 active site. Furthermore, the binding of this compound and its displacement from the active site can be followed by fluorescence measurements, which allows a rapid evaluation of the CYP 3A4 affinity of any new drug candidate. (C) 2003 Elsevier Ltd. All rights reserved.