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Sains Malaysiana 55(5)(2026): 898-914
http://doi.org/10.17576/jsm-2026-5505-12
Synthesis, In Silico Study, and In Vitro Essay of Pyridazinone-Hydrazone Hybrid as Inhibitor for α-Glucosidase
(Sintesis, Kajian In silico dan Esei In Vitro Hibrid Piridazinon-Hidrazon sebagai Perencat α-Glukosidase)
YUNI
FATISA1,2, HENLI HENLI1, NENI FRIMAYANTI3,
HILWAN YUDA TERUNA1 & JASRIL JASRIL1,*
1Department of Chemistry,
Faculty of Mathematics and Natural Sciences, Universitas Riau, Pekanbaru (28293), Indonesia
2Department of Chemistry
Education, Faculty of Tarbiyah and Keguruan, Universitas Islam
Negeri Sultan Syarif Kasim Riau, Pekanbaru (28293), Indonesia
3Department of Pharmacy, Sekolah Tinggi Ilmu Farmasi Riau, Pekanbaru (28293),
Indonesia
Diserahkan: 16 Oktober 2025/Diterima: 28 April 2026
Abstract
Although pyridazinone derivatives as
α-glucosidase inhibitors have been reported as potential
α-glucosidase inhibitors, studies in this area remains limited, and
require further studies exploration. Current α-glucosidase inhibitor
therapies, such as acarbose, are effective but may cause undesirable side
effects in some patients. This study aimed to synthesise new pyridazinone-hydrazone hybrids (7a–f) and
evaluate their potential as α-glucosidase inhibitors targeting the 3A4A
receptor. The compounds were synthesized by reacting compound 5 with
various hydrazines via a microwave-assisted
addition-elimination reaction. Structural characterizations were performed
using FTIR, HRMS, 1H-NMR, and 13C-NMR spectroscopy.
Antidiabetic activity was investigated using molecular docking with MOE 2024,
density functional theory (DFT) calculations with GaussView 5.0, in vitro α-glucosidase inhibition assays, and ADMET
predictions using the pkCSM and ProTo-x-II
servers. Microwave irradiation enabled the efficient synthesis of the target
compounds (7a-f) in good yields with significantly reduced reaction
times (3-10 min). Molecular docking predicted favorable binding free energies
comparable to acarbose and indicated stable non-covalent interactions with key
residues in the enzyme active site. DFT analysis showed favorable electronic
properties with small HOMO-LUMO energy gaps for the synthesized complexes. In
vitro assays confirmed that compounds 7a–c exhibited strong
inhibitory activity, with IC50 values of 26.33, 18.80, and 12.35 μg/mL, respectively,
although acarbose remained more potent (IC50 = 0.01 μg/mL). ADMET
predictions indicated potential limitations in terms of oral bioavailability.
These findings highlight pyridazinone–hydrazone hybrids as promising α-glucosidase
inhibitors and suggest that further structure–activity relationship (SAR)
optimization is required to improve their pharmacokinetic properties.
Keywords: ADMET; DFT; molecular docking; pyridazinone;
α-glucosidase enzyme
Abstrak
Walaupun kajian berkaitan potensi terbitan piridazinone sebagai perencat α-glukosidase telah dilaporkan, tetapi penyelidikannya masih terhad dan keputusan yang diperoleh memerlukan penambahbaikan selanjutnya. Terapi perencat α-glukosidase seperti akarbose telah terbukti berkesan tetapi mempunyai kesan sampingan. Objektif penyelidikan ini adalah untuk mensintesis hibrid piridazinone-hidrazon (7a-f), menganalisis keberkesanannya merencat aktiviti α-glukosidase (3A4A). Sintesis sebatian7a-f dijalankan melalui tindak balas antara sebatian 5 dan pelbagai kumpulan hidrazin menggunakan penyinaran gelombang mikro melalui tindak balas penambahan-penyingkiran. Pencirian produk menggunakanspektroskopi FTIR, HRMS, 1H-NMR
dan 13C-NMR. Aktiviti α-glukosidase (3A4A) dinilai melalui pendokan molekul menggunakan perisian MOE 2024.0901 dan DFT menggunakan perisian Gaussian view 5.0, ujian in vitro profil α-glukosidase dan meramalkan profil ADMET menggunakan pKCSm dan ProTox II. Kaedah penyinaran gelombang mikro membolehkan sintesis sebatian (7a-f) memberikan hasil yang baik dengan masa tindak balas yang cepat (3-10 min). Pendokan molekul menunjukkan sebatian7a-f mempunyai nilai tenaga bebas pengikat hampir sama dengan akarbose, membentuk interaksi bukan kovalen dan membentuk sentuhan dengan residu pada tapak aktif reseptor. Analisis DFT menunjukkan sifat elektronik yang baik dan tenaga HOMO-LUMO GAP
yang kecil. Ujian in
vitro menunjukkan bahawa akarbose adalah perencat yang sangat aktif (IC50 0.01 μg/mL), manakala sebatian7a-c aktif sebagai perencat α-glukosidase dengan nilai IC50 26.33, 18.80 dan 12.35 μg/mL. Kajian farmakokinetik memberikan cabaran utama untuk bioketersediaan oral. Analisis struktur-aktiviti hubungan (SAR) diperlukan untuk mereka bentuk sebatian terbitan baharu daripada hibrid piridazinon-hidrazon ini yang boleh mengekalkan potensi perencatan yang berkesan tetapi dengan sifat farmakokinetik yang lebih baik.
Kata kunci: ADMET;
DFT; enzim α-glukosidase; pendokan molekul; piridazinon
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*Pengarang untuk surat-menyurat; email: jasril.k@lecturer.unri.ac.id
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