4-(4-oxo-4H-chromen-2-yl)benzohydrazide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 4-(4-oxo-4H-chromen-2-yl)benzohydrazide
• 英文别名: 4-(4-Oxochromen-2-yl)benzohydrazide；4-(4-oxochromen-2-yl)benzohydrazide
• 化学式: C₁₆H₁₂N₂O₃
• 分子量: 280.283
• InChiKey: WXYGSHTYNOUSJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-二甲氧基苯甲醛 、 4-(4-oxo-4H-chromen-2-yl)benzohydrazide 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 以71%的产率得到(E)-N'-(3,5-dimethoxybenzylidene)-4-(4-oxo-4H-chromen-2-yl)benzohydrazide
  参考文献：
  名称：

  Synthesis of novel flavone hydrazones: In-vitro evaluation of α-glucosidase inhibition, QSAR analysis and docking studies

  摘要：

  Thirty derivatives of flavone hydrazone (5-34) had been synthesized through a five-step reaction and screened for their a-glucosidase inhibition activity. Chalcone 1 was synthesized through aldol condensation then subjected through oxidative cyclization, esterification, and condensation reaction to afford the final products. The result for baker's yeast alpha-glucosidase (EC 3.2.1.20) inhibition assay showed that all compounds are active with reference to the IC50 value of the acarbose (standard drug) except for compound 3. Increase in activity observed for compounds 2 to 34 clearly highlights the importance of flavone, hydrazide and hydrazone linkage in suppressing the activity of a-glucosidase. Additional functional group on N-benzylidene moiety further enhances the activity significantly. Compound 5 (15.4 +/- 0.22 mu M), a 2,4,6-trihydroxy substituted compound, is the most active compound in the series. Other compounds which were found to be active are those having chlorine, fluorine, and nitro substituents. Compounds with methoxy, pyridine, and methyl substituents are weakly active. Further studies showed that they are not active in inhibiting histone deacetylase activity and do not possess any cytotoxic properties. QSAR model was being developed to further identify the structural requirements contributing to the activity. Using Discovery Studio (DS) 2.5, various 2D descriptors were being used to develop the model. The QSAR model is able to predict the pIC(50) and could be used as a prediction tool for compounds having the same skeletal framework. Molecular docking was done for all compounds using homology model of alpha-glucosidase to identify important binding modes responsible for inhibition activity. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.017
• 作为产物：
  描述：

  methyl 4-(4-oxo-4H-chromen-2-yl)benzoate 在 hydrazine hydrate 作用下， 以 甲醇 为溶剂， 生成 4-(4-oxo-4H-chromen-2-yl)benzohydrazide
  参考文献：
  名称：

  合成 Chromen-4-One-Oxadiazole 取代类似物作为有效的 β-葡萄糖醛酸酶抑制剂

  摘要：

  Chromen-4-one 取代的恶二唑类似物 1-19 已被合成、表征和评估对 β-葡萄糖醛酸酶的抑制作用。与标准 d-糖精酸 1,4 内酯 (IC50 = 48.1 ± 1.2 μM) 相比，所有类似物都表现出不同程度的 β-葡萄糖醛酸酶抑制活性，IC50 值范围在 0.8 ± 0.1–42.3 ± 0.8 μM 之间。已建立所有化合物的构效关系。进行分子对接研究以预测化合物与酶活性位点的结合相互作用。

  DOI：

  10.3390/molecules24081528

文献信息

• Synthesis of novel flavone hydrazones: In-vitro evaluation of α-glucosidase inhibition, QSAR analysis and docking studies
  作者：Syahrul Imran、Muhammad Taha、Nor Hadiani Ismail、Syed Muhammad Kashif、Fazal Rahim、Waqas Jamil、Maywan Hariono、Muhammad Yusuf、Habibah Wahab

  DOI：10.1016/j.ejmech.2015.10.017

  日期：2015.11

  Thirty derivatives of flavone hydrazone (5-34) had been synthesized through a five-step reaction and screened for their a-glucosidase inhibition activity. Chalcone 1 was synthesized through aldol condensation then subjected through oxidative cyclization, esterification, and condensation reaction to afford the final products. The result for baker's yeast alpha-glucosidase (EC 3.2.1.20) inhibition assay showed that all compounds are active with reference to the IC50 value of the acarbose (standard drug) except for compound 3. Increase in activity observed for compounds 2 to 34 clearly highlights the importance of flavone, hydrazide and hydrazone linkage in suppressing the activity of a-glucosidase. Additional functional group on N-benzylidene moiety further enhances the activity significantly. Compound 5 (15.4 +/- 0.22 mu M), a 2,4,6-trihydroxy substituted compound, is the most active compound in the series. Other compounds which were found to be active are those having chlorine, fluorine, and nitro substituents. Compounds with methoxy, pyridine, and methyl substituents are weakly active. Further studies showed that they are not active in inhibiting histone deacetylase activity and do not possess any cytotoxic properties. QSAR model was being developed to further identify the structural requirements contributing to the activity. Using Discovery Studio (DS) 2.5, various 2D descriptors were being used to develop the model. The QSAR model is able to predict the pIC(50) and could be used as a prediction tool for compounds having the same skeletal framework. Molecular docking was done for all compounds using homology model of alpha-glucosidase to identify important binding modes responsible for inhibition activity. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Synthesis of Chromen-4-One-Oxadiazole Substituted Analogs as Potent β-Glucuronidase Inhibitors
  作者：Muhammad Taha、Fazal Rahim、Muhammad Ali、Muhammad Naseem Khan、Mohammed A. Alqahtani、Yasser A. Bamarouf、Mohammed Gollapalli、Rai Khalid Farooq、Syed Adnan Ali Shah、Qamar Uddin Ahmed、Zainul Amiruddin Zakaria

  DOI：10.3390/molecules24081528

  日期：——

  Chromen-4-one substituted oxadiazole analogs 1–19 have been synthesized, characterized and evaluated for β-glucuronidase inhibition. All analogs exhibited a variable degree of β-glucuronidase inhibitory activity with IC50 values ranging in between 0.8 ± 0.1–42.3 ± 0.8 μM when compared with the standard d-saccharic acid 1,4 lactone (IC50 = 48.1 ± 1.2 μM). Structure activity relationship has been established

  Chromen-4-one 取代的恶二唑类似物 1-19 已被合成、表征和评估对 β-葡萄糖醛酸酶的抑制作用。与标准 d-糖精酸 1,4 内酯 (IC50 = 48.1 ± 1.2 μM) 相比，所有类似物都表现出不同程度的 β-葡萄糖醛酸酶抑制活性，IC50 值范围在 0.8 ± 0.1–42.3 ± 0.8 μM 之间。已建立所有化合物的构效关系。进行分子对接研究以预测化合物与酶活性位点的结合相互作用。