5-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-3-[4-[(2,2,2-trifluoroacetyl)amino]phenyl]-3,4-dihydropyrazole-5-carboxamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-3-[4-[(2,2,2-trifluoroacetyl)amino]phenyl]-3,4-dihydropyrazole-5-carboxamide
• 化学式: C₂₀H₁₅F₆N₅O₄
• 分子量: 503.361
• InChiKey: GGFNZICGVFBBTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  3.0
• 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：
  12

反应信息

• 作为反应物：
  描述：

  5-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-3-[4-[(2,2,2-trifluoroacetyl)amino]phenyl]-3,4-dihydropyrazole-5-carboxamide 在 三氟乙酸 作用下， 生成 3-methyl-5-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-3,4-dihydro-2H-pyrazole-3-carboxylic acid (4-nitro-3-trifluoromethyl-phenyl)-amide
  参考文献：
  名称：

  Design, Synthesis, and in Vivo SAR of a Novel Series of Pyrazolines as Potent Selective Androgen Receptor Modulators

  摘要：

  A novel series of pyrazolines 2 have been designed, synthesized, and evaluated by in vivo screening as tissue-selective androgen receptor modulators (SARMs). Structure- activity relationships (SAR) were investigated at the R-1 to R-6 positions as well as the core pyrazoline ring and the anilide linker. Overall, strong electron-withdrawing groups at the RI and 2 positions and a small group at the R1 and RI position are optimal for AR agonist activity. The (S)-isomer of 7c exhibits more potent AR agonist activity than the corresponding (R)-isomer. (S)-7c exhibited an overall partial androgenic effect but full anabolic effect via oral administration in castrated rats. It demonstrated a noticeable antiandrogenic effect on prostate in intact rats with endogenous testosterone. Thus, (S)-7c is a tissue-selective nonsteroidal androgen receptor modulator with agonist activity on muscle and mixed agonist and antagonist activity on prostate.

  DOI：

  10.1021/jm0613976
• 作为产物：
  描述：

  4-(三氟乙酰氨基)苯甲醛 在 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 5-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-3-[4-[(2,2,2-trifluoroacetyl)amino]phenyl]-3,4-dihydropyrazole-5-carboxamide
  参考文献：
  名称：

  Design, Synthesis, and in Vivo SAR of a Novel Series of Pyrazolines as Potent Selective Androgen Receptor Modulators

  摘要：

  A novel series of pyrazolines 2 have been designed, synthesized, and evaluated by in vivo screening as tissue-selective androgen receptor modulators (SARMs). Structure- activity relationships (SAR) were investigated at the R-1 to R-6 positions as well as the core pyrazoline ring and the anilide linker. Overall, strong electron-withdrawing groups at the RI and 2 positions and a small group at the R1 and RI position are optimal for AR agonist activity. The (S)-isomer of 7c exhibits more potent AR agonist activity than the corresponding (R)-isomer. (S)-7c exhibited an overall partial androgenic effect but full anabolic effect via oral administration in castrated rats. It demonstrated a noticeable antiandrogenic effect on prostate in intact rats with endogenous testosterone. Thus, (S)-7c is a tissue-selective nonsteroidal androgen receptor modulator with agonist activity on muscle and mixed agonist and antagonist activity on prostate.

  DOI：

  10.1021/jm0613976