(E)-7-chloro-4-[2-(4-hydroxybenzylidene)hydrazinyl]quinoline | 1395918-92-9

• 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: (E)-7-chloro-4-[2-(4-hydroxybenzylidene)hydrazinyl]quinoline
• 英文别名: (E)-4-((2-(7-chloroquinolin-4-yl)hydrazono)methyl)phenol；4-[(E)-[(7-chloro-4-quinolyl)hydrazono]methyl]phenol；4-[(E)-[(7-chloroquinolin-4-yl)hydrazinylidene]methyl]phenol
• CAS: 1395918-92-9
• 化学式: C₁₆H₁₂ClN₃O
• 分子量: 297.744
• InChiKey: VAOZIGNCIRWVGN-VXLYETTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-7-chloro-4-[2-(4-hydroxybenzylidene)hydrazinyl]quinoline 在 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.0h， 生成 (Z)-1-(4-chlorophenyl)-2-(4-((E)-(2-(7-chloroquinolin-4-yl)hydrazono)methyl)phenoxy)-3-(2,4-dichlorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and in vitro evaluation of new chloroquine-chalcone hybrids against chloroquine-resistant strain of Plasmodium falciparum

  摘要：

  The control of malaria has been complicated with increasing resistance of malarial parasite against existing antimalarials. Herein, we report the synthesis of a new series of chloroquine-chalcone based hybrids (8-22) and their antimalarial efficacy against both chloroquine-susceptible (3D7) and chloroquine-resistant (K1) strains of Plasmodium falciparum. Most of the compounds showed enhanced antimalarial activity as compared to chloroquine in chloroquine-resistant (K1) strain of Plasmodium falciparum. Furthermore, to unfold the mechanism of action of these synthesized hybrid molecules, we carried out hemin dependent studies, in which three compounds were found to be active. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.028
• 作为产物：
  描述：

  4,7-二氯喹啉 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 (E)-7-chloro-4-[2-(4-hydroxybenzylidene)hydrazinyl]quinoline
  参考文献：
  名称：

  Synthesis and in vitro evaluation of new chloroquine-chalcone hybrids against chloroquine-resistant strain of Plasmodium falciparum

  摘要：

  The control of malaria has been complicated with increasing resistance of malarial parasite against existing antimalarials. Herein, we report the synthesis of a new series of chloroquine-chalcone based hybrids (8-22) and their antimalarial efficacy against both chloroquine-susceptible (3D7) and chloroquine-resistant (K1) strains of Plasmodium falciparum. Most of the compounds showed enhanced antimalarial activity as compared to chloroquine in chloroquine-resistant (K1) strain of Plasmodium falciparum. Furthermore, to unfold the mechanism of action of these synthesized hybrid molecules, we carried out hemin dependent studies, in which three compounds were found to be active. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.028

文献信息

• 10.1016/j.molstruc.2024.138528
  作者：Pereira, Gabriel Rodrigues Coutinho、Fraga, Letícia de Souza、de Jesus, Romulo Pereira、Queiroz, Rafael Compan、Leite, Beatriz de Frias、Alves, Marina Amaral、de Mesquita, Joelma Freire、de Souza, Alessandra Mendonça Teles、da Silva, Leandro Louback、Rodrigues, Carlos Rangel、Cabral, Lucio Mendes、Abrahim-Vieira, Barbara de Azevedo、Barbosa, Maria Leticia de Castro

  DOI：10.1016/j.molstruc.2024.138528

  日期：——

  promising pharmacological strategy for managing inflammatory-related diseases. This study describes the synthesis, as well as the and evaluation, of a series of 7‑chloro-quinolines designed as novel MPO inhibitors. Among the synthetic analogs, compounds , and emerged as the most potent enzyme inhibitors. The pharmacokinetic and toxicological assessments of these compounds pointed to their drug-likeness

  鉴于髓过氧化物酶 (MPO) 在炎症中的核心作用，MPO 抑制被认为是治疗炎症相关疾病的一种有前途的药理学策略。本研究描述了一系列被设计为新型 MPO 抑制剂的 7-氯喹啉的合成、评估和评估。在合成的类似物、化合物中，并成为最有效的酶抑制剂。这些化合物的药代动力学和毒理学评估指出了它们的药物相似性和有利的药代动力学特征，但引起了对其潜在毒性的一些担忧。此外，分析阐明了它们的结合谱，发现其与先前描述的几种抑制剂的先前结果一致，表明化合物抑制 MPO 的能力主要来自与催化三联体残基的相互作用。此外，分子动力学表明，化合物，最有效的 MPO 抑制剂，在模拟过程中始终保持活性位点内的密切相互作用，从而重申了复合物的稳定性。这项研究确定了一种新型化学类别的 7-氯喹啉 MPO 抑制剂，突出了衍生物的潜力，并作为未来和研究其安全性和抗炎活性的有希望的候选者。
• Synthesis and in vitro evaluation of new chloroquine-chalcone hybrids against chloroquine-resistant strain of Plasmodium falciparum
  作者：Koneni V. Sashidhara、Srinivasa Rao Avula、Gopala Reddy Palnati、Shiv Vardan Singh、Kumkum Srivastava、Sunil K. Puri、J.K. Saxena

  DOI：10.1016/j.bmcl.2012.07.028

  日期：2012.9

  The control of malaria has been complicated with increasing resistance of malarial parasite against existing antimalarials. Herein, we report the synthesis of a new series of chloroquine-chalcone based hybrids (8-22) and their antimalarial efficacy against both chloroquine-susceptible (3D7) and chloroquine-resistant (K1) strains of Plasmodium falciparum. Most of the compounds showed enhanced antimalarial activity as compared to chloroquine in chloroquine-resistant (K1) strain of Plasmodium falciparum. Furthermore, to unfold the mechanism of action of these synthesized hybrid molecules, we carried out hemin dependent studies, in which three compounds were found to be active. (C) 2012 Elsevier Ltd. All rights reserved.