N-(4-bromobenzyl)-1,3,5-trimethyl-1H-pyrazol-4-amine | 1152826-59-9

• 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-(4-bromobenzyl)-1,3,5-trimethyl-1H-pyrazol-4-amine
• 英文别名: N-[(4-bromophenyl)methyl]-1,3,5-trimethylpyrazol-4-amine
• CAS: 1152826-59-9
• 化学式: C₁₃H₁₆BrN₃
• mdl: MFCD11160809
• 分子量: 294.194
• InChiKey: RKZYZLYDWOYPBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  29.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,3,5-三甲基-吡唑-4-胺 、 对溴溴苄 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以43%的产率得到N-(4-bromobenzyl)-1,3,5-trimethyl-1H-pyrazol-4-amine
  参考文献：
  名称：

  Discovery of a Novel Class of Orally Active Trypanocidal N-Myristoyltransferase Inhibitors

  摘要：

  N-Myristoyltransferase (NMT) represents a promising drug target for human African trypanosomiasis (HAT), which is caused by the parasitic protozoa Trypanosoma brucei. We report the optimization of a high throughput screening hit (1) to give a lead molecule DDD85646 (63), which has potent activity against the enzyme (IC50 = 2 nM) and T. brucei (EC50 = 2 nM) in culture. The compound has good oral pharmacokinetics and cures rodent models of peripheral HAT infection. This compound provides an excellent tool for validation of T. brucei NMT as a drug target for HAT as well as a valuable lead for further optimization.

  DOI：

  10.1021/jm201091t

文献信息

• Discovery of a Novel Class of Orally Active Trypanocidal <i>N</i>-Myristoyltransferase Inhibitors
  作者：Stephen Brand、Laura A. T. Cleghorn、Stuart P. McElroy、David A. Robinson、Victoria C. Smith、Irene Hallyburton、Justin R. Harrison、Neil R. Norcross、Daniel Spinks、Tracy Bayliss、Suzanne Norval、Laste Stojanovski、Leah S. Torrie、Julie A. Frearson、Ruth Brenk、Alan H. Fairlamb、Michael A. J. Ferguson、Kevin D. Read、Paul G. Wyatt、Ian H. Gilbert

  DOI：10.1021/jm201091t

  日期：2012.1.12

  N-Myristoyltransferase (NMT) represents a promising drug target for human African trypanosomiasis (HAT), which is caused by the parasitic protozoa Trypanosoma brucei. We report the optimization of a high throughput screening hit (1) to give a lead molecule DDD85646 (63), which has potent activity against the enzyme (IC50 = 2 nM) and T. brucei (EC50 = 2 nM) in culture. The compound has good oral pharmacokinetics and cures rodent models of peripheral HAT infection. This compound provides an excellent tool for validation of T. brucei NMT as a drug target for HAT as well as a valuable lead for further optimization.