6,6-dimethyl-1-(4-nitrophenyl)-1,5,6,7-tetrahydro-4H-indazol-4-one | 58635-20-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6,6-dimethyl-1-(4-nitrophenyl)-1,5,6,7-tetrahydro-4H-indazol-4-one
• 英文别名: 6,6-dimethyl-1-(4-nitro-phenyl)-1,5,6,7-tetrahydro-indazol-4-one；1-p-Nitrophenyl-6,7-dihydro-6,6-dimethylindazol-4(5H)-on；6,6-Dimethyl-1-(4-nitrophenyl)-5,7-dihydroindazol-4-one
• CAS: 58635-20-4
• 化学式: C₁₅H₁₅N₃O₃
• 分子量: 285.302
• InChiKey: WZMAEABDJQOUOK-UHFFFAOYSA-N

物化性质

• 沸点：
  452.5±33.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,6-dimethyl-1-(4-nitrophenyl)-1,5,6,7-tetrahydro-4H-indazol-4-one 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis of new indazole based dual inhibitors of α-glucosidase and α-amylase enzymes, their in vitro, in silico and kinetics studies

  摘要：

  The current study describes the discovery of novel inhibitors of alpha-glucosidase and a-amylase enzymes. For that purpose, new hybrid analogs of N-hydrazinecarbothioamide substituted indazoles 4-18 were synthesized and fully characterized by EI-MS, FAB-MS, HRFAB-MS, H-1-, and C-13 NMR spectroscopic techniques. Stereochemistry of the imine double bond was established by NOESY measurements. All derivatives 4-18 with their intermediates 1-3, were evaluated for in vitro alpha-glucosidase and a-amylase enzyme inhibition. It is worth mentioning that all synthetic compounds showed good inhibition potential in the range of 1.54 +/- 0.02-4.89 +/- 0.02 mu M for alpha-glucosidase and for alpha-amylase 1.42 +/- 0.04-4.5 +/- 0.18 mu M in comparison with the standard acarbose (IC50 value of 1.36 +/- 0.01 mu M). In silico studies were carried out to rationalize the mode of binding interaction of ligands with the active site of enzymes. Moreover, enzyme inhibitory kinetic characterization was also performed to understand the mechanism of enzyme inhibition.

  DOI：

  10.1016/j.bioorg.2019.103195
• 作为产物：
  描述：

  5,5-Dimethyl-2-[N'-(4-nitro-phenyl)-hydrazinomethylene]-cyclohexane-1,3-dione 生成 6,6-dimethyl-1-(4-nitrophenyl)-1,5,6,7-tetrahydro-4H-indazol-4-one
  参考文献：
  名称：

  NUNN A. J.; ROWELL F. J., J. CHEM. SOC. PERKIN TRANS PART 1, , 1975, NO 23, 2435-2438 D=#2+

  摘要：

  DOI：

文献信息

• Synthesis of new indazole based dual inhibitors of α-glucosidase and α-amylase enzymes, their in vitro, in silico and kinetics studies
  作者：Rafaila Rafique、Khalid Mohammed Khan、Arshia、Kanwal、Sridevi Chigurupati、Abdul Wadood、Ashfaq Ur Rehman、Arunkumar Karunanidhi、Shehryar Hameed、Muhammad Taha、Mariya al-Rashida

  DOI：10.1016/j.bioorg.2019.103195

  日期：2020.1

  The current study describes the discovery of novel inhibitors of alpha-glucosidase and a-amylase enzymes. For that purpose, new hybrid analogs of N-hydrazinecarbothioamide substituted indazoles 4-18 were synthesized and fully characterized by EI-MS, FAB-MS, HRFAB-MS, H-1-, and C-13 NMR spectroscopic techniques. Stereochemistry of the imine double bond was established by NOESY measurements. All derivatives 4-18 with their intermediates 1-3, were evaluated for in vitro alpha-glucosidase and a-amylase enzyme inhibition. It is worth mentioning that all synthetic compounds showed good inhibition potential in the range of 1.54 +/- 0.02-4.89 +/- 0.02 mu M for alpha-glucosidase and for alpha-amylase 1.42 +/- 0.04-4.5 +/- 0.18 mu M in comparison with the standard acarbose (IC50 value of 1.36 +/- 0.01 mu M). In silico studies were carried out to rationalize the mode of binding interaction of ligands with the active site of enzymes. Moreover, enzyme inhibitory kinetic characterization was also performed to understand the mechanism of enzyme inhibition.
• NUNN A. J.; ROWELL F. J., J. CHEM. SOC. PERKIN TRANS PART 1, <JCPK-BH>, 1975, NO 23, 2435-2438 D=#2+
  作者：NUNN A. J.、 ROWELL F. J.

  DOI：——

  日期：——