6-hydroxy-4'-dimethylaminoaurone | 637753-80-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: 6-hydroxy-4'-dimethylaminoaurone
• 英文别名: NL-28；2-[[4-(Dimethylamino)phenyl]methylidene]-6-hydroxy-1-benzofuran-3-one
• CAS: 637753-80-1
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: XWVDODMZYGXNEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-hydroxy-4'-dimethylaminoaurone 在 4-二甲氨基吡啶 、 甲酸 、 氨基磺酰氯 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  WO2023/114761

  摘要：

  公开号：
• 作为产物：
  描述：

  2',4'-dihydroxy-4-dimethylaminochalcone 在 mercury(II) diacetate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以43%的产率得到6-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

文献信息

• 6-芳氧乙酰氧基橙酮类化合物及其在农药上的 应用
  申请人：江苏大学

  公开号：CN104072455B

  公开（公告）日：2016-06-15

  本发明6-芳氧乙酰氧基橙酮类化合物及其在农药上的应用,属于除草剂技术领域。本发明6-芳氧乙酰氧基橙酮类化合物是下述通式化合物：；其中，R1:氢、卤素、C1-C4卤代烷基、C1-C4烷基、C1-C4烷氧基、C1-C4烷氨基；R2:氢、C1-C4烷基。本发明提供了许多新的化学结构和新化合物。生物活性测定结果表明，化合物Ⅰ具有很高的除草活性。
• Some morpholine tethered novel aurones: Design, synthesis, biological, kinetic and molecular docking studies
  作者：Bhavna Saroha、Gourav Kumar、Priyanka Arya、Neera Raghav、Suresh Kumar

  DOI：10.1016/j.bioorg.2023.106805

  日期：2023.11

  the hybrids were evaluated for their intracellular (cathepsin B) and extracellular (trypsin, lipase, amylase) enzyme inhibition potencies. The in-vitro inhibition screening against cathepsin B revealed that most of the synthesized compounds are good competitive inhibitors (% inhibition = 22.91–75.04), with 6q (% inhibition = 75.04) and 6r (% inhibition = 71.13) as the eminent inhibitors of the series

  酶是生物大分子，已成为重要的药物靶点，因为酶的上调/失衡会导致各种病理状况，例如炎症、寄生虫感染、阿尔茨海默病、癌症等。在这里，我们设计并合成了一些吗啉束缚的新型橙酮，并评估它们作为 CTSB、α-淀粉酶、脂肪酶和胰蛋白酶激活剂的潜在抑制剂。所有新合成的化合物均通过各种光谱技术（1 H NMR、13 C NMR、HRMS）进行了充分表征，并根据单晶 XRD 数据和1 H NMR 化学位移值指定了它们的Z构型。此外，还评估了杂交体的细胞内（组织蛋白酶 B）和细胞外（胰蛋白酶、脂肪酶、淀粉酶）​​酶抑制效力。针对组织蛋白酶 B 的体外抑制筛选表明，大多数合成的化合物都是良好的竞争性抑制剂（抑制百分比 = 22.91–75.04），其中6q（抑制百分比 = 75.04）和6r（抑制百分比 = 71.13）是最有效的抑制剂。该系列。同时，它们对淀粉酶（抑制百分比 = 7.22–22.48）和脂肪酶（抑制百分比
• 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.
• WO2023/114761
  申请人：——

  公开号：——

  公开（公告）日：——