7-Chloro-4-(4-phenylpiperazin-1-yl)quinoline | 353257-17-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 7-Chloro-4-(4-phenylpiperazin-1-yl)quinoline
• CAS: 353257-17-7
• 化学式: C₁₉H₁₈ClN₃
• 分子量: 323.825
• InChiKey: SHBIVVWFJHADHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  19.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-4-(methylthio)-3-nitro-4H-chromen-2-amine 、 7-Chloro-4-(4-phenylpiperazin-1-yl)quinoline 以 乙醇 为溶剂， 反应 6.0h， 以83%的产率得到N-benzyl-4-(4-(4-(7-chloroquinolin-4-yl)piperazin-1-yl)phenyl)-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：

  4,7-二氯喹啉 、 N-苯基哌嗪 以 乙醇 为溶剂， 反应 2.0h， 以98%的产率得到7-Chloro-4-(4-phenylpiperazin-1-yl)quinoline
  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

文献信息

• [EN] ACTIVATORS OF CYLINDRICAL PROTEASES<br/>[FR] ACTIVATEURS DES PROTÉASES CYLINDRIQUES
  申请人：UNIV TORONTO

  公开号：WO2012079164A1

  公开（公告）日：2012-06-21

  The present invention is directed to activators of cylindrical proteases ("ACPs"), particularly ClpP, and the role thereof in the diagnosis and treatment of bacterial infections. A number of ACPs were identified that activate caseinolytic protease P ("ClpP"), which independently can only degrade small peptides. In the presence of ACPs, ClpP may be activated to allow it to degrade larger proteins, hence, abolishing the specificity arising from the ATP-dependent chaperones. Members of the ACPs were found to have bactericidal activity. As such, ACPs represent a new classes of compounds that can activate ClpP and that can be developed as potential novel antibiotics.

  本发明涉及圆柱形蛋白酶（“ACPs”）的激活剂，特别是ClpP，以及其在细菌感染的诊断和治疗中的作用。已经确定了许多激活酪蛋白酶P（“ClpP”）的ACP，独立地只能降解小肽。在存在ACP的情况下，ClpP可以被激活，使其能够降解更大的蛋白质，从而消除了ATP依赖的分子伴侣引起的特异性。发现了ACP成员具有杀菌活性。因此，ACP代表了一类新的化合物，可以激活ClpP，并可以作为潜在的新型抗生素开发。
• Synthesis, in vitro and in silico antimalarial activity of 7-chloroquinoline and 4H-chromene conjugates
  作者：A. Parthiban、J. Muthukumaran、Ashan Manhas、Kumkum Srivastava、R. Krishna、H. Surya Prakash Rao

  DOI：10.1016/j.bmcl.2015.08.030

  日期：2015.10

  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.