N-(3-bromopropyl)quinoline-2-carboxamide

• 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: N-(3-bromopropyl)quinoline-2-carboxamide
• 化学式: C₁₃H₁₃BrN₂O
• mdl: MFCD11133316
• 分子量: 293.163
• InChiKey: LDTLPDIPBRTMCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2,4-dichlorophenyl)piperazine hydrochloride 、 N-(3-bromopropyl)quinoline-2-carboxamide 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 以42%的产率得到N-(3-(4-(2,4-dichlorophenyl)piperazin-1-yl)propyl)quinoline-2-carboxamide
  参考文献：
  名称：

  Design, synthesis and docking study of 4-arylpiperazine carboxamides as monoamine neurotransmitters reuptake inhibitors

  摘要：

  Rational drug design method has been used to generate 4-arylpiperazine carboxamides in an effort to develop safer, more potent and effective monoamine neurotransmitters reuptake inhibitors. Out of twenty-seven synthesized compounds, compound 9 displayed potent monoamine neurotransmitter reuptake inhibitory activity against HEK cells transfected with hSERT or hNET. A Surflex-Dock docking model of 9 was also studied.

  DOI：

  10.1016/j.bmc.2018.06.043
• 作为产物：
  描述：

  喹哪啶酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(3-bromopropyl)quinoline-2-carboxamide
  参考文献：
  名称：

  Design and synthesis of 4-benzylpiperidine carboxamides as dual serotonin and norepinephrine reuptake inhibitors

  摘要：

  A series of 4-benzylpiperidine carboxamides were designed and synthesized, and tested for their dual (serotonin and norepinephrine) reuptake inhibition. The synthesis of 4-benzylpiperidine carboxamides involved two main steps: amidation and substitution. Derivatives with 3 carbon linker displayed better activity than with 2 carbon linker. 4-Biphenyl- and 2-naphthyl-substituted derivatives 7e and 7j showed greater dual reuptake inhibition than standard drug venlafaxine HCl. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.08.022

文献信息

• Design, synthesis and biological evaluation of novel aminopropylcarboxamide derivatives as sigma ligands
  作者：Daniele Zampieri、Sara Fortuna、Maurizio Romano、Emanuele Amata、Maria Dichiara、Agostino Marrazzo、Lorella Pasquinucci、Rita Turnaturi、Maria Grazia Mamolo

  DOI：10.1016/j.bmcl.2022.128860

  日期：2022.9

  novel sigma receptor (SR) ligands, we present the design, synthesis and binding studies of a small library of aminopropylcarboxamide derivatives, obtained from a deconstruction of the piperidine ring of previously synthesized piperidine-based compounds. The best results were achieved with benzofuran (5c, 5g) and quinoline (5a, 5e) derivatives. These compounds revealed the highest affinity for both receptor

  在我们不断努力开发新的 σ 受体 (SR) 配体的过程中，我们提出了一个小型氨基丙基甲酰胺衍生物库的设计、合成和结合研究，该库是从先前合成的基于哌啶的化合物的哌啶环的解构中获得的。苯并呋喃（5c，5g）和喹啉（5a，5e）衍生物的效果最好。这些化合物显示出对两种受体亚型的最高亲和力。特别是 3,4-二甲氧基苯基衍生物5e和5g对 S2R 表现出最高的选择性，尤其是喹啉衍生物5e对 S2R 亚型的亲和力高出 35 倍。针对广泛用于乳腺癌研究的 SKBR3 和 MCF7 细胞系评估了上述化合物的细胞毒活性。尽管5g的效力与西拉美新和氟哌啶醇在两种细胞系中的效力相似，但化合物5a、5c和5e在 SKBR3 细胞中表现出至少与氟哌啶醇相当的效力。对 S2R 结合位点的分子模型评估证实了化合物5e的强相互作用，从而证明了其最高的 S2R 亲和力。
• Design and synthesis of 4-benzylpiperidine carboxamides as dual serotonin and norepinephrine reuptake inhibitors
  作者：Suresh Paudel、Yongkai Cao、Shuohan Guo、Byeongkwan An、Kyeong-Man Kim、Seung Hoon Cheon

  DOI：10.1016/j.bmc.2015.08.022

  日期：2015.10

  A series of 4-benzylpiperidine carboxamides were designed and synthesized, and tested for their dual (serotonin and norepinephrine) reuptake inhibition. The synthesis of 4-benzylpiperidine carboxamides involved two main steps: amidation and substitution. Derivatives with 3 carbon linker displayed better activity than with 2 carbon linker. 4-Biphenyl- and 2-naphthyl-substituted derivatives 7e and 7j showed greater dual reuptake inhibition than standard drug venlafaxine HCl. (C) 2015 Elsevier Ltd. All rights reserved.
• Design, synthesis and docking study of 4-arylpiperazine carboxamides as monoamine neurotransmitters reuptake inhibitors
  作者：Suresh Paudel、Ningning Sun、Daulat Bikram Khadka、Goon Yoon、Kyeong-Man Kim、Seung Hoon Cheon

  DOI：10.1016/j.bmc.2018.06.043

  日期：2018.8

  Rational drug design method has been used to generate 4-arylpiperazine carboxamides in an effort to develop safer, more potent and effective monoamine neurotransmitters reuptake inhibitors. Out of twenty-seven synthesized compounds, compound 9 displayed potent monoamine neurotransmitter reuptake inhibitory activity against HEK cells transfected with hSERT or hNET. A Surflex-Dock docking model of 9 was also studied.