2',5'-dihydroxy-4-dimethylaminochalcone | 215095-39-9

• 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: 2',5'-dihydroxy-4-dimethylaminochalcone
• 英文别名: 4'-dimethylamino-2,5-dihydroxychalcone；1-(2,5-Dihydroxyphenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one；1-(2,5-dihydroxyphenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one
• CAS: 215095-39-9
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: MHVFCVMAJIDJMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2',5'-dihydroxy-4-dimethylaminochalcone 在 mercury(II) diacetate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以49%的产率得到5-hydroxy-4'-dimethylaminoaurone
  参考文献：
  名称：

  Synthesis, docking studies and antioxidant activity of some chalcone and aurone derivatives

  摘要：

  Chalcones and aurones are found to possess high antioxidant activity. They are known to inhibit tyrosinase enzyme involved in synthesis of melanin. A series of substituted chalcones and aurones have been synthesized and tested for their antioxidant activity. Postulated structures of the newly synthesized compounds are in agreement with their IR, H-1 NMR and MS. The docking study of this series of compounds was performed on crystal structure of tyrosinase from Bacillus megaterium using VlifeMDS 3.0 software. Antioxidant activity data obtained from four methods, i.e., DPPH free radical scavenging assay, iron chelating assay, reducing power assay and hydrogen peroxide scavenging assay, indicate that the activity increased with dimethylamino group on position 4/4' of ring B as evident from the significant activities of SB7 and SB8 in case of chalcones and aurones, respectively. The poor activities of SB4 and SB5 in DPPH scavenging ability and reducing power assays could be because of presence of chloro group on B-ring. Furthermore, the activity is facilitated with the presence of hydroxyl group on A-ring (preferably on position 5/5') in both chalcones and aurones.

  DOI：

  10.1007/s00044-012-0413-3
• 作为产物：
  描述：

  对二甲氨基苯甲醛 、 2,5-二羟基苯乙酮 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 2',5'-dihydroxy-4-dimethylaminochalcone
  参考文献：
  名称：

  A Novel Colorimetric and Fluorescent Anion Chemosensor Based on the Flavone Quasi-crown Ether−Metal Complex

  摘要：

  The metal-ligand complex 1 ([Mg (L)] (2+)) (or 2 ([Ca (L)] (2+))) was demonstrated to selectively bind HSO4- (or H2PO4-) over other anions by using UV-vis absorption and fluorescence spectroscopy. The studied complex exhibits the remarkable color change and fluorescence quenching upon introducing HSO4- (or H2PO4-) anion in acetonitrile. Both the mechanism and structure of the secondary complex of complex 1 with anion were proposed on the basis of theoretical computation.

  DOI：

  10.1021/ol035818e

文献信息

• A Novel Colorimetric and Fluorescent Anion Chemosensor Based on the Flavone Quasi-crown Ether−Metal Complex
  作者：Li-Li Zhou、Hao Sun、Hua-Ping Li、Hui Wang、Xiao-Hong Zhang、Shi-Kang Wu、Shuit-Tong Lee

  DOI：10.1021/ol035818e

  日期：2004.4.1

  The metal-ligand complex 1 ([Mg (L)] (2+)) (or 2 ([Ca (L)] (2+))) was demonstrated to selectively bind HSO4- (or H2PO4-) over other anions by using UV-vis absorption and fluorescence spectroscopy. The studied complex exhibits the remarkable color change and fluorescence quenching upon introducing HSO4- (or H2PO4-) anion in acetonitrile. Both the mechanism and structure of the secondary complex of complex 1 with anion were proposed on the basis of theoretical computation.
• Synthesis, docking studies and antioxidant activity of some chalcone and aurone derivatives
  作者：Tamanna Narsinghani、Mukesh C. Sharma、Sakshi Bhargav

  DOI：10.1007/s00044-012-0413-3

  日期：2013.9

  Chalcones and aurones are found to possess high antioxidant activity. They are known to inhibit tyrosinase enzyme involved in synthesis of melanin. A series of substituted chalcones and aurones have been synthesized and tested for their antioxidant activity. Postulated structures of the newly synthesized compounds are in agreement with their IR, H-1 NMR and MS. The docking study of this series of compounds was performed on crystal structure of tyrosinase from Bacillus megaterium using VlifeMDS 3.0 software. Antioxidant activity data obtained from four methods, i.e., DPPH free radical scavenging assay, iron chelating assay, reducing power assay and hydrogen peroxide scavenging assay, indicate that the activity increased with dimethylamino group on position 4/4' of ring B as evident from the significant activities of SB7 and SB8 in case of chalcones and aurones, respectively. The poor activities of SB4 and SB5 in DPPH scavenging ability and reducing power assays could be because of presence of chloro group on B-ring. Furthermore, the activity is facilitated with the presence of hydroxyl group on A-ring (preferably on position 5/5') in both chalcones and aurones.