N-methyl-N'-(4-acetamido-benzylidene)hydrazine | 20131-82-2

• 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: N-methyl-N'-(4-acetamido-benzylidene)hydrazine
• 英文别名: N-[4-[(methylhydrazinylidene)methyl]phenyl]acetamide
• CAS: 20131-82-2
• 化学式: C₁₀H₁₃N₃O
• 分子量: 191.233
• InChiKey: ZASGACLWAYUOBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  53.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-methyl-N'-(4-acetamido-benzylidene)hydrazine 在 N-氯代丁二酰亚胺 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-acetamido-N-methyl-benzenecarbohydrazonoyl chloride
  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：

  对乙酰氨基苯甲醛 、 对甲苯磺酰肼 以 甲醇 为溶剂， 生成 N-methyl-N'-(4-acetamido-benzylidene)hydrazine
  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

文献信息

• Design, Synthesis, and in Vivo SAR of a Novel Series of Pyrazolines as Potent Selective Androgen Receptor Modulators
  作者：Xuqing Zhang、Xiaojie Li、George F. Allan、Tifanie Sbriscia、Olivia Linton、Scott G. Lundeen、Zhihua Sui

  DOI：10.1021/jm0613976

  日期：2007.8.1

  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.