2-((3-((7-chloroquinolin-4-yl)amino)propyl)amino)-naphthalene-1,4-dione | 1256837-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-((3-((7-chloroquinolin-4-yl)amino)propyl)amino)-naphthalene-1,4-dione
• 英文别名: 2-[3-[(7-Chloroquinolin-4-yl)amino]propylamino]naphthalene-1,4-dione
• CAS: 1256837-72-5
• 化学式: C₂₂H₁₈ClN₃O₂
• 分子量: 391.857
• InChiKey: GMWYTQUOYKZOLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,7-二氯喹啉 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 53.0h， 生成 2-((3-((7-chloroquinolin-4-yl)amino)propyl)amino)-naphthalene-1,4-dione
  参考文献：
  名称：

  通过体外和计算机评估评估的作为细胞毒剂的合成烯胺萘醌衍生自指甲花醌

  摘要：

  我们合成了十种烯胺萘醌，产率在 43% 到 76% 之间。通过 MTT 测定法筛选这些化合物对四种类型的人类癌细胞系 HCT116、PC3、HL60 和 SNB19 的体外抗增殖活性。带有甲基吡啶 ( 7 ) 和喹啉 ( 12 ) 部分的萘醌是最活跃的（所有细胞系的 IC 50  < 24 μM），与对照药物获得的值相当或更好。计算机评估使我们能够建立定性的结构-活性关系，这表明静电特征，特别是C 2 -C 3核间斥力和分子偶极矩，与生物反应有关。此外，分子对接模拟表明，合成化合物具有通过抑制拓扑异构酶-II 和胸苷酸合酶作为抗癌分子的潜力。

  DOI：

  10.1016/j.bmcl.2021.128419

文献信息

• Parallel Synthesis, Evaluation, and Preliminary Structure−Activity Relationship of 2,5-Diamino-1,4-benzoquinones as a Novel Class of Bivalent Anti-Prion Compound
  作者：Salvatore Bongarzone、Hoang Ngoc Ai Tran、Andrea Cavalli、Marinella Roberti、Paolo Carloni、Giuseppe Legname、Maria Laura Bolognesi

  DOI：10.1021/jm100882t

  日期：2010.11.25

  A library of 11 entries, featuring a 2,5-diamino-1,4-benzoquinones nucleus as spacer connecting two aromatic prion recognition motifs, was designed and evaluated against prion infection. Notably. 6-chloro-1,2,3,4-tetrithydroacridine 10 showed an EC50 of 0.17 mu M, which was lower than that displayed by reference compound BiCappa. More importantly, 10 possessed the capability to contrast prion fibril formation and oxidative stress, together with a low cytotoxicity. This study further corroborates the bivalent strategy as a viable approach to the rational design of anti-prion chemical probes.
• Synthesis, Molecular Modelling and Anticancer Activities of New Molecular Hybrids Containing 1,4-Naphthoquinone, 7-Chloroquinoline, 1,3,5-Triazine and Morpholine Cores as PI3K and AMPK Inhibitors in the Metastatic Melanoma Cells
  作者：Rodolfo Fiorot、Regina Westphal、Bárbara Lemos、Rodrigo Romagna、Paola Gonçalves、Maruska Fernandes、Carmen Ferreira、Alex Taranto、Sandro Greco

  DOI：10.21577/0103-5053.20190096

  日期：——

  Three molecular hybrids containing 1,4-naphtlioquinones, 1.3,5-triazines, morpholine and 7-chloroquinoline, which have recognized contributions to the biological activity of many drugs. were synthesized in yields ranging from 43-84%. All hybrids were obtained in three steps starting from readily available reactants: lawsone, cyanuric chloride. morpholine and 4,7-dichloroquinoline. A previous docking study was carried out to identify the binding energy and pharmacophore conformation of the promising anticancer compounds with PI3K gamma (phosphoinositide 3-kinase) and AMPK (5' AMP-activated protein kinase). The cancer activity in human metastatic melanoma cells (SKMEL-103) were performed, and the synthetized compounds presented half maximal inhibitory concentration (IC50) values around 25 mu M. The expressions of PI3K and AMPK were also determined using western blotting technique, and all molecular hybrids negatively modulated both targets.
• Synthetic enamine naphthoquinone derived from lawsone as cytotoxic agents assessed by in vitro and in silico evaluations
  作者：Bárbara C. Lemos、Regina Westphal、Eclair Venturini Filho、Rodolfo G. Fiorot、José Walkimar M. Carneiro、Anne Caroline C. Gomes、Celina J. Guimarães、Fátima C.E. de Oliveira、Pedro Mikael S. Costa、Claudia Pessoa、Sandro J. Greco

  DOI：10.1016/j.bmcl.2021.128419

  日期：2021.12

  We synthesized ten enamine naphthoquinones with yields ranging from 43 to 76%. These compounds were screened for their in vitro antiproliferative activities by MTT assay against four types of human cancer cell lines: HCT116, PC3, HL60 and SNB19. The naphthoquinones bearing the picolylamine (7) and quinoline (12) moieties were the most actives (IC50 < 24 μM for all the cell lines), which were comparable

  我们合成了十种烯胺萘醌，产率在 43% 到 76% 之间。通过 MTT 测定法筛选这些化合物对四种类型的人类癌细胞系 HCT116、PC3、HL60 和 SNB19 的体外抗增殖活性。带有甲基吡啶 ( 7 ) 和喹啉 ( 12 ) 部分的萘醌是最活跃的（所有细胞系的 IC 50  < 24 μM），与对照药物获得的值相当或更好。计算机评估使我们能够建立定性的结构-活性关系，这表明静电特征，特别是C 2 -C 3核间斥力和分子偶极矩，与生物反应有关。此外，分子对接模拟表明，合成化合物具有通过抑制拓扑异构酶-II 和胸苷酸合酶作为抗癌分子的潜力。