2-(4-octyl-piperazin-1-yl)-6-nitroquinoline | 1344678-07-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(4-octyl-piperazin-1-yl)-6-nitroquinoline
• 英文别名: 2-(4-Octyl-piperazin-1-yl)-6-nitroquinoline (8)；6-nitro-2-(4-octylpiperazin-1-yl)quinoline
• CAS: 1344678-07-4
• 化学式: C₂₁H₃₀N₄O₂
• 分子量: 370.495
• InChiKey: XDJGGKOIRQGFEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  65.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氯喹啉 在 硫酸 、 硝酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 70.5h， 生成 2-(4-octyl-piperazin-1-yl)-6-nitroquinoline
  参考文献：
  名称：

  Synthesis, Antidepressant Evaluation and Docking Studies of Long-Chain Alkylnitroquipazines as Serotonin Transporter Inhibitors

  摘要：

  Twelve alkyl analogues (1–12) of the high‐affinity serotonin transporter (SERT) inhibitor 6‐nitroquipazine (6‐NQ) were synthesized and studied using in vitro radioligand competition binding assays to determine their binding affinity (Ki). The putative antidepressant activity of five of the binders with the highest SERT binding affinities was studied by the forced swim and locomotor activity mouse tests. The three‐dimensional (3D) structures of 8 and 9 were determined using NOE NMR technique. Flexible docking of the compounds was undertaken to illustrate the binding of the compounds in the SERT model. Our results showed that several of the 6‐NQ analogues are high‐affinity SERT inhibitors and indicated that the octyl (8), decyl (10) and dodecyl (12) 6‐NQ analogues exhibit moderate antidepressant activity.

  DOI：

  10.1111/cbdd.12116

文献信息

• Synthesis, Antidepressant Evaluation and Docking Studies of Long-Chain Alkylnitroquipazines as Serotonin Transporter Inhibitors
  作者：Mari Gabrielsen、Karol Wołosewicz、Anna Zawadzka、Jerzy Kossakowski、Gabriel Nowak、Małgorzata Wolak、Katarzyna Stachowicz、Agata Siwek、Aina W. Ravna、Irina Kufareva、Lech Kozerski、Elżbieta Bednarek、Jerzy Sitkowski、Wojciech Bocian、Ruben Abagyan、Andrzej J. Bojarski、Ingebrigt Sylte、Zdzisław Chilmonczyk

  DOI：10.1111/cbdd.12116

  日期：2013.6

  Twelve alkyl analogues (1–12) of the high‐affinity serotonin transporter (SERT) inhibitor 6‐nitroquipazine (6‐NQ) were synthesized and studied using in vitro radioligand competition binding assays to determine their binding affinity (Ki). The putative antidepressant activity of five of the binders with the highest SERT binding affinities was studied by the forced swim and locomotor activity mouse tests. The three‐dimensional (3D) structures of 8 and 9 were determined using NOE NMR technique. Flexible docking of the compounds was undertaken to illustrate the binding of the compounds in the SERT model. Our results showed that several of the 6‐NQ analogues are high‐affinity SERT inhibitors and indicated that the octyl (8), decyl (10) and dodecyl (12) 6‐NQ analogues exhibit moderate antidepressant activity.