(±)-1-(4-fluorophenylsulfonyl)-3-methylpiperazine

• 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: (±)-1-(4-fluorophenylsulfonyl)-3-methylpiperazine
• 英文别名: 1-(4-fluorobenzenesulfonyl)-3-methylpiperazine；1-(4-Fluorophenyl)sulfonyl-3-methylpiperazine
• 化学式: C₁₁H₁₅FN₂O₂S
• mdl: MFCD19291991
• 分子量: 258.317
• InChiKey: OLSMUHZTADQCDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-acetyl-N-(3-chloro-4-methylphenyl)-N-(3-chloropropyl)piperidine-4-carboxamide 、 (±)-1-(4-fluorophenylsulfonyl)-3-methylpiperazine 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以26%的产率得到(±)-1-acetyl-N-(3-chloro-4-methylphenyl)-N-(3-(4-(4-fluorophenylsulfonyl)-2-methylpiperazin-1-yl)propyl)piperidine-4-carboxamide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel 2-methylpiperazine derivatives as potent CCR5 antagonists

  摘要：

  Three series of novel 2-methylpiperazine derivatives were designed and synthesized using a fragment-assembly strategy. Among them, six compounds (13, 16, 18, 22, 33, and 36) showed potent activity against CCR5 comparable to that of the positive control, maraviroc, in calcium mobilization assay. Moreover, some compounds were selected and further tested for their antiviral activity in HIV-1 single cycle assay. As a result, four compounds (13, 16, 33, and 36) showed antiviral activity at the nanomolar level. Additionally, the potent four compounds showed no cytotoxicity at a concentration of 10 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.052
• 作为产物：
  描述：

  4-氟苯磺酰氯 、 2-甲基哌嗪 在 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 1.5h， 以64%的产率得到(±)-1-(4-fluorophenylsulfonyl)-3-methylpiperazine
  参考文献：
  名称：

  Molecular Simplification of 1,4-Diazabicyclo[4.3.0]nonan-9-ones Gives Piperazine Derivatives That Maintain High Nootropic Activity

  摘要：

  Several 4-substituted 1-acylpiperazines, obtained by molecular simplification of 4-substituted 1,4-diazabicyclo[4.3.0]nonan-9-ones, have been synthesized and tested in vivo on the mouse passive avoidance test, to evaluate their nootropic activity. The results show that, apparently, an N-acylpiperazine group can mimic the 2-pyrrolidinone ring of 1,4-diazabicyclo[4.3.0]nonan-9-one, as the compounds of the new series maintain high nootropic activity. Moreover molecular simplification produces more clear-cut structure-activity relationships with respect to the parent series. The mechanism of action also appears to be similar in the two series. In fact, although the molecular mechanism remains to be elucidated, the most potent compound of each class (DM232 and 13, DM235) is able to increase acetylcholine release in rat brain. Piperazine derivatives represent a new class of nootropic drugs with an in vivo pharmacological profile very similar to that of piracetam, showing much higher potency with respect to the reference compound. Among the compounds studied, 13 (DM235) shows outstanding potency, being active at a dose of 0.001 mg kg(-1) sc.

  DOI：

  10.1021/jm000972h