3,3,3-trifluoro-2-hydroxy-2-{[(4-nitrophenyl)sulfanyl]methyl}propanoic acid | 90357-36-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,3,3-trifluoro-2-hydroxy-2-{[(4-nitrophenyl)sulfanyl]methyl}propanoic acid
• 英文别名: 3,3,3-Trifluoro-2-hydroxy-2-[(4-nitrophenyl)sulfanylmethyl]propanoic acid
• CAS: 90357-36-1
• 化学式: C₁₀H₈F₃NO₅S
• 分子量: 311.238
• InChiKey: YZWKLRCNQNKXSB-UHFFFAOYSA-N

物化性质

• 沸点：
  491.4±45.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,3,3-trifluoro-2-hydroxy-2-{[(4-nitrophenyl)sulfanyl]methyl}propanoic acid 在 盐酸 、 氯化亚砜 、 calcium carbonate 、 tin(ll) chloride 作用下， 以 甲醇 、 N,N-二甲基乙酰胺 、 乙腈 为溶剂， 反应 144.0h， 生成 2-[(4-acetamidophenyl)sulfanylmethyl]-3,3,3-trifluoro-2-hydroxy-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
  参考文献：
  名称：

  Novel nonsteroidal ligands with high binding affinity and potent functional activity for the androgen receptor

  摘要：

  While nonsteroidal androgen receptor (AR) antagonists have been known for many years, and used in the clinic for the treatment of hormone dependent prostate cancer, very little is known about nonsteroidal AR agonists. We designed and synthesized a series of chiral bicalutamide analogs, which bear electron-withdrawing groups (either a cyano or a nitro group at the 4-position and a trifluoromethyl group at the 3-position) in the aromatic A ring, and different substituents at the para position in the aromatic B ring of the parent molecule. We also synthesized a series of racemic bicalutamide analogs, which have a trifluoromethyl group instead of a methyl group at the R, position. We examined AR binding affinities of our compounds in a competitive binding assay with a radiolabeled high affinity AR ligand, H-3-mibolerone, and also measured their abilities to stimulate AR-mediated transcriptional activation in a cotransfection assay. These studies demonstrated that (1) nonsteroidal ligands can be structurally modified from known nonsteroidal antiandrogens to generate, ligands capable of activating AR-mediated transcriptional activation. (2) R-isomer analogs exhibit higher AR binding affinity and more potent functional activity than their corresponding S-isomers in all cases. (3) All sulphide analogs show higher AR binding affinity and more potent functional activity than their corresponding sulphone analogs, with the exception of ligand R-8. Those ligands which exhibit high AR binding affinity and potent functional activity for human AR may provide effective clinical uses for male fertility, male contraception, and hormone replacement therapy. (C) 2002 Editions scientifiques et medicales Elsevier SAS.-All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01335-1
• 作为产物：
  描述：

  1,1,1-trifluoro-3-[(4-nitrophenyl)sulfanyl]acetone 在 盐酸 、 硫酸 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 44.0h， 生成 3,3,3-trifluoro-2-hydroxy-2-{[(4-nitrophenyl)sulfanyl]methyl}propanoic acid
  参考文献：
  名称：

  Novel nonsteroidal ligands with high binding affinity and potent functional activity for the androgen receptor

  摘要：

  While nonsteroidal androgen receptor (AR) antagonists have been known for many years, and used in the clinic for the treatment of hormone dependent prostate cancer, very little is known about nonsteroidal AR agonists. We designed and synthesized a series of chiral bicalutamide analogs, which bear electron-withdrawing groups (either a cyano or a nitro group at the 4-position and a trifluoromethyl group at the 3-position) in the aromatic A ring, and different substituents at the para position in the aromatic B ring of the parent molecule. We also synthesized a series of racemic bicalutamide analogs, which have a trifluoromethyl group instead of a methyl group at the R, position. We examined AR binding affinities of our compounds in a competitive binding assay with a radiolabeled high affinity AR ligand, H-3-mibolerone, and also measured their abilities to stimulate AR-mediated transcriptional activation in a cotransfection assay. These studies demonstrated that (1) nonsteroidal ligands can be structurally modified from known nonsteroidal antiandrogens to generate, ligands capable of activating AR-mediated transcriptional activation. (2) R-isomer analogs exhibit higher AR binding affinity and more potent functional activity than their corresponding S-isomers in all cases. (3) All sulphide analogs show higher AR binding affinity and more potent functional activity than their corresponding sulphone analogs, with the exception of ligand R-8. Those ligands which exhibit high AR binding affinity and potent functional activity for human AR may provide effective clinical uses for male fertility, male contraception, and hormone replacement therapy. (C) 2002 Editions scientifiques et medicales Elsevier SAS.-All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01335-1