2-hydroxy-3-((5-methylfuran-2-yl)methyl)-1,4-naphthoquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-3-((5-methylfuran-2-yl)methyl)-1,4-naphthoquinone
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: XXWADEVWQDEJFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.51
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-((5-methylfuran-2-yl)methyl)-1,4-naphthoquinone 、 cobalt(II) diacetate tetrahydrate 以 乙醇 为溶剂， 反应 1.0h， 以87%的产率得到[Co(2-hydroxy-3-((5-methylfuran-2-yl)methyl)-1,4-naphthoquinone)₂]_n
  参考文献：
  名称：

  Preparation of new metallic complexes from 2-hydroxy-3-((5-methylfuran-2-yl)methyl)-1,4-naphthoquinone

  摘要：

  In this work, two series of copper, zinc, niquel, cobalt and manganese complexes have been synthesized and characterized. The first one was prepared from 2-hydroxy-3-((5-methylfuran-2-yl)methyl)-1,4-naphthoquinone (1) (NQ) as ligand and the second one from the ligands 2-hydroxy-3-((5-methylfuran-2-yl)methyl)-1,4-naphthoquinone (NQ) and phenantroline (Phen). In the first series, a 1D polymer was obtained for all metallic complexes while in the second series, the phenantroline ligand avoids the polymerization. The complexes were characterized by elemental analyses, IR spectroscopy and X-ray crystallography. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2019.114280
• 作为产物：
  描述：

  2-甲基呋喃 、 聚合甲醛 、 2-羟基-1,4-萘醌 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 以46%的产率得到2-hydroxy-3-((5-methylfuran-2-yl)methyl)-1,4-naphthoquinone
  参考文献：
  名称：

  在人早幼粒细胞白血病HL-60细胞系中具有细胞毒活性的萘醌衍生物的合成和药效基团建模。

  摘要：

  催化剂/ HypoGen药效团建模方法和三维定量结构-活性关系（3D-QSAR）/比较分子相似性指数分析（CoMSIA）方法已成功用于解释一组测试的51种天然和合成萘醌衍生物的细胞毒活性在人早幼粒细胞白血病HL-60细胞系中。计算模型促进了对抗肿瘤特性至关重要的配体结构元素的鉴定。高活性β-环-吡喃-1,2-萘醌[0.1 microM

  DOI：

  10.1021/jm060849b

文献信息

• Synthesis and Pharmacophore Modeling of Naphthoquinone Derivatives with Cytotoxic Activity in Human Promyelocytic Leukemia HL-60 Cell Line
  作者：Elisa Pérez-Sacau、Raquel G. Díaz-Peñate、Ana Estévez-Braun、Angel G. Ravelo、Jose M. García-Castellano、Leonardo Pardo、Mercedes Campillo

  DOI：10.1021/jm060849b

  日期：2007.2.1

  quantitative structure-activity relationship (3D-QSAR)/comparative molecular similarity indices analysis (CoMSIA) methods have been successfully applied to explain the cytotoxic activity of a set of 51 natural and synthesized naphthoquinone derivatives tested in human promyelocytic leukemia HL-60 cell line. The computational models have facilitated the identification of structural elements of the ligands

  催化剂/ HypoGen药效团建模方法和三维定量结构-活性关系（3D-QSAR）/比较分子相似性指数分析（CoMSIA）方法已成功用于解释一组测试的51种天然和合成萘醌衍生物的细胞毒活性在人早幼粒细胞白血病HL-60细胞系中。计算模型促进了对抗肿瘤特性至关重要的配体结构元素的鉴定。高活性β-环-吡喃-1,2-萘醌[0.1 microM
• Preparation of new metallic complexes from 2-hydroxy-3-((5-methylfuran-2-yl)methyl)-1,4-naphthoquinone
  作者：Amagoia Aguirrechu-Comerón、Sandra Oramas-Royo、Raquel Pérez-Acosta、Rita Hernández-Molina、Javier Gonzalez-Platas、Ana Estévez-Braun

  DOI：10.1016/j.poly.2019.114280

  日期：2020.2

  In this work, two series of copper, zinc, niquel, cobalt and manganese complexes have been synthesized and characterized. The first one was prepared from 2-hydroxy-3-((5-methylfuran-2-yl)methyl)-1,4-naphthoquinone (1) (NQ) as ligand and the second one from the ligands 2-hydroxy-3-((5-methylfuran-2-yl)methyl)-1,4-naphthoquinone (NQ) and phenantroline (Phen). In the first series, a 1D polymer was obtained for all metallic complexes while in the second series, the phenantroline ligand avoids the polymerization. The complexes were characterized by elemental analyses, IR spectroscopy and X-ray crystallography. (C) 2019 Elsevier Ltd. All rights reserved.