Phenyl-thiocarbamic acid O-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl] ester | 121569-79-7

• 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: Phenyl-thiocarbamic acid O-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl] ester
• 英文别名: O-[[(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]] N-phenylcarbamothioate
• CAS: 121569-79-7
• 化学式: C₃₄H₅₃NOS
• 分子量: 523.867
• InChiKey: NVQYKMDHASVQLO-QPSWIEMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Phenyl-thiocarbamic acid O-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl] ester 以 六甲基磷酰三胺 、 水 为溶剂， 以52%的产率得到5alpha-胆甾烷
  参考文献：
  名称：

  活性炭光化活性碳还原剂

  摘要：

  的氨基甲酸酯类，硫代氨基甲酸酯和碳酸光还原发生在HMPTH的混合物2烷烃的更好的产率为硫代氨基甲酸盐观察到O.甲。从反应混合物中也分离出甲酸盐和光炸产品。甚至在HMPA中，自由基中间体也可能被环己烯捕获。

  DOI：

  10.1016/s0040-4039(00)87649-2
• 作为产物：
  描述：

  3β-胆甾烷醇 、 硫代异氰酸苯酯 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 Phenyl-thiocarbamic acid O-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl] ester
  参考文献：
  名称：

  Syntheses and Biological Activities of a Novel Group of Steroidal Derived Inhibitors for Human CDC25A Protein Phosphatase

  摘要：

  Silica gel supported pyrolysis of an azido-homo-oxa steroid led to rearrangement, presumably by a mechanism similar to that of solution phase Schmidt fragmentation, to produce a group of novel inhibitors for the oncogenic cell cycle regulator Cdc25A phosphatase. Cyano-containing acid 17, one of the best inhibitors in this group, inhibited the activity of Cdc25A protein phosphatase reversibly and noncompetitively with an IC50 value of 2.2 muM Structure-activity relationships revealed that a phosphate surrogate such as a carboxyl or a xanthate group is required for inhibitory activity, and a hydrophobic alkyl chain, such as the cholesteryl side chain, contributes greatly to the potency. Without the cyano group, acid 26 and xanthate 27 were found to be more selective over Cdc25A (IC50 = 5.1 muM and 1.1 muM, respectively) than toward CD45 (IC50 > 100 muM, in each case), a receptor protein tyrosine phosphatase. Several of these inhibitors showed antiproliferative activities in the NCI 60-human tumor cell line screen. These steroidal derived Cdc25 inhibitors provide unique leads for the development of dual-specificity protein phosphatase inhibitors.

  DOI：

  10.1021/jm0004401

文献信息

• Syntheses and Biological Activities of a Novel Group of Steroidal Derived Inhibitors for Human CDC25A Protein Phosphatase
  作者：Hairuo Peng、Wenge Xie、Diane M. Otterness、John P. Cogswell、Randy T. McConnell、H. Luke Carter、Garth Powis、Robert T. Abraham、Leon H. Zalkow

  DOI：10.1021/jm0004401

  日期：2001.3.1

  Silica gel supported pyrolysis of an azido-homo-oxa steroid led to rearrangement, presumably by a mechanism similar to that of solution phase Schmidt fragmentation, to produce a group of novel inhibitors for the oncogenic cell cycle regulator Cdc25A phosphatase. Cyano-containing acid 17, one of the best inhibitors in this group, inhibited the activity of Cdc25A protein phosphatase reversibly and noncompetitively with an IC50 value of 2.2 muM Structure-activity relationships revealed that a phosphate surrogate such as a carboxyl or a xanthate group is required for inhibitory activity, and a hydrophobic alkyl chain, such as the cholesteryl side chain, contributes greatly to the potency. Without the cyano group, acid 26 and xanthate 27 were found to be more selective over Cdc25A (IC50 = 5.1 muM and 1.1 muM, respectively) than toward CD45 (IC50 > 100 muM, in each case), a receptor protein tyrosine phosphatase. Several of these inhibitors showed antiproliferative activities in the NCI 60-human tumor cell line screen. These steroidal derived Cdc25 inhibitors provide unique leads for the development of dual-specificity protein phosphatase inhibitors.
• Photoréactivité de dérivés de l'acide carbonique en milieu réducteur
  作者：Vénimégué Albert Dembélé、Henri Deshayes、Jean-Pierre Pete

  DOI：10.1016/s0040-4039(00)87649-2

  日期：1982.1

  Photoreduction of carbamates, thiocarbamates and carbonate occurs in a mixture of HMPTH2O. A better yield of alkane is observed for thiocarbamates. Formates and photoFries products are also isolated from the reaction mixture. Radical intermediates can be trapped by cyclohexene even in HMPA.

  的氨基甲酸酯类，硫代氨基甲酸酯和碳酸光还原发生在HMPTH的混合物2烷烃的更好的产率为硫代氨基甲酸盐观察到O.甲。从反应混合物中也分离出甲酸盐和光炸产品。甚至在HMPA中，自由基中间体也可能被环己烯捕获。