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<p>In search for novel α-amylase inhibitors, the present study reports an efficient protocol for the synthesis of 2-pyrazoline derivatives, which involves an Amberlyst-15-catalyzed (3 + 2) annulation reaction of chalcones with phenylhydrazine or semicarbazide at room temperature. The structures were confirmed by spectroscopic analysis, and among the series, the compound 5-(4-(dimethylamino)phenyl)-3-(4-methylphenyl)-4,5-dihydro-1<i>H</i>-pyrazole-1-carboxamide <b>5c</b>, was confirmed through single crystal X-ray diffraction studies. The analysis revealed the presence of intermolecular C–H...O and N–H...O hydrogen bond interactions. The molecular structure was stabilized by C–H...π and π...π molecular interactions. The intermolecular N–H...O interaction leads to the formation of an R<sub>2</sub><sup>2</sup>(8) supramolecular synthon. The preliminary <i>in vitro</i> α-amylase inhibition assay studies of compounds <b>4</b>(<b>a</b>–<b>d</b>) and <b>5</b>(<b>a</b>–<b>d</b>) indicated the promising inhibitory effects. The compounds demonstrated good α-amylase inhibition with IC<sub>50</sub> values ranging from 2.23 to 9.16 µM, with the most potent inhibitors being <b>5b</b> (IC<sub>50</sub> = 2.23 µM) and <b>4b</b> (IC<sub>50</sub> = 3.86 µM), in comparison to the control drug acarbose (IC<sub>50</sub> = 2.56&#xa0;µM).</p> Graphical abstract <p>In search of potent anti-diabetic agents, a series of pyrazoles <b>4</b>(<b>a</b>–<b>d</b>) and pyrazole carboxamides <b>5</b>(<b>a</b>–<b>d</b>) were synthesised through Amberlyst-15 catalysed reaction of chalcones <b>3</b>(<b>a</b>–<b>d</b>) with phenylhydrazine/semicarbazide hydrochloride in acetonitrile medium at room temperature. The crystallographic studies confirm the structure of <b>5c</b>. The newly synthesised compounds were evaluated for α-amylase activity, and the results revealed that <b>4b</b> and <b>5b</b> exhibit the most potent activities.</p>

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Design, synthesis, crystal structure, spectral characterization of new pyrazole derivatives and their α-amylase inhibitory potential

  • 期刊论文

  • 发表日期：

    2026年3月26日

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  • Dinesh Kumar Govindappa,
  • Karthik Kumara,
  • Swati Mylarappa,
  • Neratur Krishnappagowda Lokanath,
  • Kariyappa Ajay Kumar,
  • Hanasavadi Parameshwarappa Jayadevappa

摘要

In search for novel α-amylase inhibitors, the present study reports an efficient protocol for the synthesis of 2-pyrazoline derivatives, which involves an Amberlyst-15-catalyzed (3 + 2) annulation reaction of chalcones with phenylhydrazine or semicarbazide at room temperature. The structures were confirmed by spectroscopic analysis, and among the series, the compound 5-(4-(dimethylamino)phenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide 5c, was confirmed through single crystal X-ray diffraction studies. The analysis revealed the presence of intermolecular C–H...O and N–H...O hydrogen bond interactions. The molecular structure was stabilized by C–H...π and π...π molecular interactions. The intermolecular N–H...O interaction leads to the formation of an R22(8) supramolecular synthon. The preliminary in vitro α-amylase inhibition assay studies of compounds 4(a–d) and 5(a–d) indicated the promising inhibitory effects. The compounds demonstrated good α-amylase inhibition with IC50 values ranging from 2.23 to 9.16 µM, with the most potent inhibitors being 5b (IC50 = 2.23 µM) and 4b (IC50 = 3.86 µM), in comparison to the control drug acarbose (IC50 = 2.56 µM).

Graphical abstract

In search of potent anti-diabetic agents, a series of pyrazoles 4(a–d) and pyrazole carboxamides 5(a–d) were synthesised through Amberlyst-15 catalysed reaction of chalcones 3(a–d) with phenylhydrazine/semicarbazide hydrochloride in acetonitrile medium at room temperature. The crystallographic studies confirm the structure of 5c. The newly synthesised compounds were evaluated for α-amylase activity, and the results revealed that 4b and 5b exhibit the most potent activities.