1-(4-bromo-1-hydroxy-naphthalen-2-yl)-3-(4-methoxy-phenyl)-propenone | 109865-87-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(4-bromo-1-hydroxy-naphthalen-2-yl)-3-(4-methoxy-phenyl)-propenone
• CAS: 109865-87-4
• 化学式: C₂₀H₁₅BrO₃
• 分子量: 383.241
• InChiKey: VPJOWOKCUHLIKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(4-bromo-1-hydroxy-naphthalen-2-yl)-3-(4-methoxy-phenyl)-propenone 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 5-(4''-Methoxy)-phenyl-3-(1'-hydroxy-4'-brom)naphthyl-(2')-isooxazolin
  参考文献：
  名称：

  Warty,A.S.; Jadhav,G.V., Journal of the Indian Chemical Society, 1973, vol. 50, p. 488 - 491

  摘要：

  DOI：

文献信息

• Synthesis, characterization, antimicrobial screening and cytotoxic properties of Cu(II) and Zn(II) complexes with bidentate hydroxylated 1,3-diaryl-2-propene-1-ones ligand
  作者：Pravinkumar Patil、Sainath Zangade

  DOI：10.2298/jsc200901068z

  日期：——

  A series of binary metal complexes (halo, hydroxyl and methoxy substituted bis(2-(E)acryloyl)naphthalen-1-yl)oxy)Cu(II) and Zn(II) (C1? ?C10)) of Cu2+ and Zn2+ ions derived from bi-coordinated hydroxylated 1,3- -diaryl-2-propene-1-ones were synthesized. The newly synthesized metal complexes were structurally determined by FT-IR, 1H-NMR, 13C-NMR, ESR spectral, XRD and TGA analyses. The FT-IR and ESR studies demonstrated that interactions between metal ions with ligands occur through carbonyl oxygen and deprotonated hydroxyl oxygen and correspond to square-planar geometry for all complexes. The metal complexes were screened in-vitro and evaluated for their antimicrobial and cytotoxic activities. The complexes C1 and C4 showed significant antimicrobial activity while the remaining complexes showed moderate antimicrobial activity against the tested pathogens. The complexes were evaluated for cytotoxic activity against the organism Artemia salina. Complexes C2?C5 exhibited LC50 values of 630.45, 969.99, 921.94 and 918.41 ?M mL-1, respectively. Furthermore, the complexes were evaluated for their anticancer activity against the liver cancer cell line Hep G2 in comparison with the 5-fluorouracil standard. Complex C5 showed a significant IC50 value of 58.94 ?g mL-1. Therefore, the present study is useful for the development of a new class of antimicrobial and anticancer agents.

  从双配位羟基 1,3- 二芳基-2-丙烯-1-酮中合成了一系列 Cu2+ 和 Zn2+ 离子的二元金属配合物（卤素、羟基和甲氧基取代的双（2-(E)丙烯酰基）萘-1-基）Cu(II) 和 Zn(II) (C1??C10)。通过 FT-IR、1H-NMR、13C-NMR、ESR 光谱、XRD 和 TGA 分析确定了新合成的金属配合物的结构。傅立叶变换红外光谱和 ESR 研究表明，金属离子与配体之间的相互作用是通过羰基氧和去质子化羟基氧发生的，并且所有配合物都符合方形几何结构。对这些金属配合物进行了体外筛选，并评估了它们的抗菌和细胞毒性活性。络合物 C1 和 C4 显示出显著的抗菌活性，而其余络合物则对测试病原体显示出中等程度的抗菌活性。还评估了复合物对盐蒿属生物的细胞毒活性。复合物 C2?C5 的 LC50 值分别为 630.45、969.99、921.94 和 918.41 M mL-1。此外，与 5-氟尿嘧啶标准品相比，还评估了复合物对肝癌细胞系 Hep G2 的抗癌活性。复合物 C5 显示出明显的 IC50 值，即 58.94.g mL-1。因此，本研究有助于开发一类新的抗菌剂和抗癌剂。