3,3′((4-hydroxy-3-methoxyphenyl)methylene)bis(2-hydroxynapthelene-14-dione) | 1582250-18-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 3,3′((4-hydroxy-3-methoxyphenyl)methylene)bis(2-hydroxynapthelene-14-dione)
• 英文别名: 2,2'-[(4-hydroxy-3-methoxyphenyl)methylene]bis(3-hydroxynaphthalene-1,4-dione)
• CAS: 1582250-18-7
• 化学式: C₂₈H₁₈O₈
• 分子量: 482.446
• InChiKey: LZXCZOOWYVQASJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  36.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  138.2
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  2-羟基-1,4-萘醌 、 香草醛 在 溶剂黄146 、 β-丙氨酸 作用下， 反应 2.0h， 以34%的产率得到3,3′((4-hydroxy-3-methoxyphenyl)methylene)bis(2-hydroxynapthelene-14-dione)
  参考文献：
  名称：

  新型抗寄生虫双萘醌衍生物

  摘要：

  测试了一系列通过芳基醛与劳松酮缩合制备的双萘醌衍生物对弓形虫和布氏锥虫寄生虫的抗寄生虫活性。单氟苯基衍生物 1a、3,4-二氟苯基类似物 1c 和呋喃基化合物 1l 对弓形虫细胞表现出显着的活性，似乎是针对这种寄生虫的新候选药物。3,4,5-三氟苯基衍生物 1g 和异香草基衍生物 1j 显示出对主要利什曼原虫无鞭毛体的选择性活性。

  DOI：

  10.1002/cbdv.201900597

文献信息

• Molecular docking, synthesis, and biological evaluation of naphthoquinone as potential novel scaffold for H5N1 neuraminidase inhibition
  作者：Garima Sharma、S. Vasanth Kumar、Habibah A. Wahab

  DOI：10.1080/07391102.2016.1274271

  日期：2018.1.2

  and evaluated against neuraminidase of H5N1 virus. p-hydroxy derivatives showed higher inhibition when compared to p-halogenated compounds. Molecular docking studies conducted with H5N1 neuraminidase clearly demonstrated different binding modes of the most active compound onto the open and closed conformations of loop 150. The results thus provide not only evidences of a novel scaffold evaluated as

  设计，合成了一系列含有天然2-羟基-1-4-萘醌部分的二聚萘醌，并针对H5N1病毒的神经氨酸酶进行了评估。与对卤代化合物相比，对羟基衍生物显示出更高的抑制作用。用H5N1神经氨酸酶进行的分子对接研究清楚地表明，最具活性的化合物在环路150的开环和闭环构象上具有不同的结合模式。因此，结果不仅提供了一种新型支架作为抑制剂的证据，而且还提供了涉及分子模型的合理解释以及循环150在绑定中的作用。
• Antileishmanial activity evaluation of bis-lawsone analogs and DNA topoisomerase-I inhibition studies
  作者：Garima Sharma、Sayan Chowdhury、Suman Sinha、Hemanta K. Majumder、S. Vasanth Kumar

  DOI：10.3109/14756366.2013.765413

  日期：2014.4.1

  For the development of potent novel antileishmanial agents, 3,3'-(arylmethylene)bis(2-hydroxynaphthalene-1,4 dione) derivatives were synthesized from lawsone and evaluated for cytotoxicity on Leishmania donovani promastigotes as well as on leishmanial DNA topoisomerase-I. Enzyme inhibition studies were conducted with simultaneous and preincubation conditions. Total inhibition is compared to camptothecin (CPT), which was taken as positive control on both the systems of enzyme inhibition. The range of activity varied from 37.5 to 70 mu M in simultaneous assay and 13-16 mu M in preincubation assay. Furthermore, when evaluated against L. donovani promastigotes, the synthesized compounds exhibited the activity ranging from 2 to 14 mu M. The results revealed that all the compounds exhibit promising antileishmanial activity.