7-Chloro-4-(1,4-diazepan-1-yl)quinoline

• 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: 7-Chloro-4-(1,4-diazepan-1-yl)quinoline
• 化学式: C₁₄H₁₆ClN₃
• mdl: MFCD05182289
• 分子量: 261.754
• InChiKey: ACGOVCPNPCHPKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.357
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-Chloro-4-(1,4-diazepan-1-yl)quinoline 在 potassium phosphate 、 copper(l) iodide 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 29.0h， 生成 4-(4-(4-(7-chloroquinolin-4-yl)-1,4-diazepan-1-yl)phenyl)-N-methyl-3-nitro-4H-chromen-2-amine
  参考文献：
  名称：

  Synthesis, in vitro and in silico antimalarial activity of 7-chloroquinoline and 4H-chromene conjugates

  摘要：

  A new series of chloroquinoline-4H-chromene conjugates incorporating piperizine or azipane tethers were synthesized and their anti-malarial activity were evaluated against two Plasmodium falciparum strains namely 3D7 chloroquine sensitive (CQS) and K1 chloroquine resistant (CQR). Chloroquine was used as the standard and also reference for comparison. The conjugates exhibit intense UV absorption with lambda(max) located at 342 nm (log epsilon = 4.0), 254 nm (log epsilon = 4.2), 223 nm (log epsilon = 4.4) which can be used to spectrometrically track the molecules even in trace amounts. Among all the synthetic compounds, two molecules namely 6-nitro and N-piperazine groups incorporated 7d and 6-chloro and N-azapane incorporated 15b chloroquinoline-4H-chromene conjugates showed significant anti-malarial activity against two strains (3D7 and K1) of P. falciparum. These values are lesser than the values of standard antimalarial compound. Molecular docking results suggested that these two compounds showing strong binding affinity with P. falciparum lactate dehydrogenase (PfLDH) and also they occupy the co-factor position which indicated that they could be the potent inhibitors for dreadful disease malaria and specifically attack the glycolytic pathway in parasite for energy production. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.08.030
• 作为产物：
  描述：

  高哌嗪 、 4,7-二氯喹啉 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以62 %的产率得到7-Chloro-4-(1,4-diazepan-1-yl)quinoline
  参考文献：
  名称：

  融合硫内酯和喹啉支架：新的潜在抗结核结合物

  摘要：

  结核病感染构成了严峻的挑战，特别是由于耐药分枝杆菌菌株的出现，凸显了开发新药的必要性。我们报告了二十四种新化合物，这些化合物是通过将硫内酯和喹啉支架聚合而设计和合成的，作为潜在的抗结核实体。细菌测定表明，其中一种缀合物 4f 是一种高效分子，最低抑菌浓度 (MIC) 值为 0.5 μg/mL，与一线药物相当。值得注意的是，缀合物 4f 对利福平和多重耐药分枝杆菌菌株表现出相似的效力，同时对正常细胞表现出很小的毒性。体内研究证明了该缀合物进一步开发的巨大潜力。最后，对四个不同靶点进行了分子对接研究，以阐明可能的作用机制。

  DOI：

  10.1016/j.molstruc.2023.137255

文献信息

• [EN] QUINOLYLPIPERAZINO SUBSTITUTED THIOLACTONE COMPOUNDS AND PROCESS FOR THE PREPARATION THEREOF<br/>[FR] COMPOSÉS DE THIOLACTONE À SUBSTITUTION QUINOLYLPIPÉRAZINO, ET PROCÉDÉ D'ÉLABORATION CORRESPONDANT
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2011138666A1

  公开（公告）日：2011-11-10

  The present invention provides compounds of general formulae A, useful as potential anti-tubercular agents against Mycobacterium tuberculosis H37Rv, and drug-resistant Mycobacterium tuberculosis and a process for the preparation thereof. Formula (A).

  本发明提供通式A的化合物，可用作潜在的抗结核药物，用于对抗结核分枝杆菌H37Rv和耐药结核分枝杆菌，并提供其制备方法。通式A如下：
• QUINOLYLPIPERAZINO SUBSTITUTED THIOLACTONE COMPOUNDS AND PROCESS FOR THE PREPARATION THEREOF
  申请人：Council of Scientific and Industrial Research

  公开号：EP2566863A1

  公开（公告）日：2013-03-13
• US9085557B2
  申请人：——

  公开号：US9085557B2

  公开（公告）日：2015-07-21