3,3'-((4-hydroxyphenyl)methylene)bis(2-hydroxynaphthalene-1,4-dione) | 1207194-43-1

• 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-hydroxyphenyl)methylene)bis(2-hydroxynaphthalene-1,4-dione)
• 英文别名: 3,3′-[(4-hydroxyphenyl)methylene]bis(2-hydroxynaphthalene-1,4-dione)；3,3′((4-hydroxy-phenyl)methylene)bis(2-hydroxynapthelene-14-dione)
• CAS: 1207194-43-1
• 化学式: C₂₇H₁₆O₇
• 分子量: 452.42
• InChiKey: HXXTYZBTPSNVSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  34.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  128.97
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  lawsone 、 对羟基苯甲醛 在 lithium chloride 作用下， 以 水 为溶剂， 反应 12.0h， 生成 3,3'-((4-hydroxyphenyl)methylene)bis(2-hydroxynaphthalene-1,4-dione)
  参考文献：
  名称：

  Antileishmanial activity evaluation of bis-lawsone analogs and DNA topoisomerase-I inhibition studies

  摘要：

  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.

  DOI：

  10.3109/14756366.2013.765413

文献信息

• An efficient approach to bis-benzoquinonylmethanes on water under catalysis of the bio-derived O-carboxymethyl chitosan
  作者：Fatereh Asghari-Haji、Kurosh Rad-Moghadam、Nosrat O. Mahmoodi

  DOI：10.1039/c5ra26580k

  日期：——

  O-Carboxymethyl chitosan was found to simulate an enzyme-like catalytic activity in the one-pot pseudo-three-component synthesis of bis-benzoquinonylmethane dyes in water.

  O-羧甲基壳聚糖在水相中的一锅法伪三组分合成双苯醌甲烷染料时被发现具有模拟酶促催化活性。

• 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。
• Selective Pro-Apoptotic Activity of Novel 3,3′-(Aryl/Alkyl-Methylene)Bis(2-Hydroxynaphthalene-1,4-Dione) Derivatives on Human Cancer Cells via the Induction Reactive Oxygen Species
  作者：Pritam Sadhukhan、Sukanya Saha、Krishnendu Sinha、Goutam Brahmachari、Parames C. Sil

  DOI：10.1371/journal.pone.0158694

  日期：——

  compared to cisplatin, thus indicating the superiority of 1j as a possible anticancer agent. This compound was observed to induce apoptosis in the glioma cells by inducing the caspase dependent apoptotic pathways via ROS and downregulating the PI3K/AKT/mTOR pathway. Estimation of different oxidative stress markers also confirms the induction of oxidative stress in 1j exposed cancer cells. The toxicity of 1j

  除了正常细胞之外，选择性诱导癌细胞凋亡被认为是对抗癌症的有效策略。在本研究中，分析了一系列二十二 (22) 种合成 3,3'-(芳基/烷基亚甲基)双(2-羟基萘-1,4-二酮)双劳松衍生物的促凋亡作用使用 MTT 测定在六种不同细胞系（五种癌性细胞系和一种正常细胞系）中检测活性。在这 22 种测试化合物中，1j 在研究中使用的不同细胞系中诱导人神经胶质瘤细胞 (CCF-4) 凋亡最有效。然后将该化合物 1j 的活性与流行的抗癌药物顺铂进行比较，顺铂因其肾毒性而使用有限。在这项研究中，与顺铂相比，1j 衍生物对正常肾细胞的毒性要小得多，从而表明 1j 作为一种可能的抗癌药物的优越性。据观察，该化合物通过 ROS 诱导 caspase 依赖性细胞凋亡途径并下调 PI3K/AKT/mTOR 途径，从而诱导神经胶质瘤细胞凋亡。对不同氧化应激标记物的估计也证实了 1j 暴露的癌细胞中氧化应激的诱导。
• 3,3′-(Arylmethylene)bis(2-hydroxynaphthalene-1,4-dione) as the Main Product of the Mannich Reaction of 2-Hydroxy-1,4-Naphthoquinone with 4<i>H</i>-1,2,4-Triazol-4-Amine and Various Aldehydes
  作者：Razieh Ghodsi、Morteza Safarnejad、Sina Omid Malayeri、Sima Golmakanion

  DOI：10.3184/174751918x15242406216491

  日期：2018.4

  The Mannich reaction of lawsone with various aldehydes and 4H-1,2,4-triazol-4-amine gave unexpected 3,3′-(arylmethylene)bis(2-hydroxynaphthalene-1,4-dione) derivatives. With 2,4-dihydroxybenzaldehyde under the same conditions, it led to the formation of 3-hydroxy-12-(3-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-6H-benzo[b]xanthene-6,11(12H)-dione instead of various triazolylaminonaphthoquinones

  劳松与各种醛和 4H-1,2,4-三唑-4-胺的曼尼希反应产生出乎意料的 3,3'-（芳基亚甲基）双（2-羟基萘-1,4-二酮）衍生物。与2,4-二羟基苯甲醛在相同条件下生成3-羟基-12-(3-羟基-1,4-二氧-1,4-二氢萘-2-基)-6H-苯并[b ]呫吨-6,11(12H)-二酮代替各种三唑基氨基萘醌。