Synthesis, α-glucosidase inhibitory activity, and molecular docking of cinnamamides

Aijijiyah, Nur Pasca; Wati, First Ambar; Rahayu, Reni; Srilistiani, Alfatchu; Mahzumi, Farah; Aulia, T R; Santoso, Liangga; Pamela, Egar; Ramadhani, Ersya Yanu; Ilfahmi, Yan Alamanda; Purnomo, Adi Setyo; Putra, Surya Rosa; Santoso, Eko Budi; Ningsih, Sri; Firdausi, Nisrina; Santoso, Mardi

doi:10.1007/s00044-023-03032-y

Cited by 5 publications

(3 citation statements)

References 58 publications

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“…Molecular docking methods can validate the binding interaction between small molecule drugs and potential targets, providing information for the potential therapeutic effects of small molecule drugs on diseases [ 17 , 18 ]. To investigate the interaction of compound P3 with different targets, we conducted molecular docking.…”

Section: Resultsmentioning

confidence: 99%

A New Potent Inhibitor against α-Glucosidase Based on an In Vitro Enzymatic Synthesis Approach

Zhang,

Che,

Jing

et al. 2024

Molecules

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Inhibiting the activity of intestinal α-glucosidase is considered an effective approach for treating type II diabetes mellitus (T2DM). In this study, we employed an in vitro enzymatic synthesis approach to synthesize four derivatives of natural products (NPs) for the discovery of therapeutic drugs for T2DM. Network pharmacology analysis revealed that the betulinic acid derivative P3 exerted its effects in the treatment of T2DM through multiple targets. Neuroactive ligand–receptor interaction and the calcium signaling pathway were identified as key signaling pathways involved in the therapeutic action of compound P3 in T2DM. The results of molecular docking, molecular dynamics (MD) simulations, and binding free energy calculations indicate that compound P3 exhibits a more stable binding interaction and lower binding energy (−41.237 kcal/mol) with α-glucosidase compared to acarbose. In addition, compound P3 demonstrates excellent characteristics in various pharmacokinetic prediction models. Therefore, P3 holds promise as a lead compound for the development of drugs for T2DM and warrants further exploration. Finally, we performed site-directed mutagenesis to achieve targeted synthesis of betulinic acid derivative. This work demonstrates a practical strategy of discovering novel anti-hyperglycemic drugs from derivatives of NPs synthesized through in vitro enzymatic synthesis technology, providing potential insights into compound P3 as a lead compound for anti-hyperglycemic drug development.

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Section: Resultsmentioning

confidence: 99%

A New Potent Inhibitor against α-Glucosidase Based on an In Vitro Enzymatic Synthesis Approach

Zhang,

Che,

Jing

et al. 2024

Molecules

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“…The crystal structure of the COX-2 protein was obtained from the Protein Data Bank (PDB ID: 5IKR) and prepared using MGLTools 1.5.6 [13]. The 3D structure of N -(5bromofuran-2-carbonyl)isonicotinohydrazide (1) was generated using the MarvinSketch tool [14]. The location of the receptor binding site was set using a grid box placed at the position of the native ligand (mefenamic acid) with a centering of x: 38.042; y: 2.131; z: 61.280, xyz dimensions of 30 × 30 × 30, and a spacing of 0.375 Å.…”

Section: Molecular Docking Studymentioning

confidence: 99%

N′-(5-Bromofuran-2-carbonyl)isonicotinohydrazide

Ramadhani

Aijijiyah

Santoso

et al. 2023

Molbank

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N′-(5-bromofuran-2-carbonyl)isonicotinohydrazide (1) was obtained in the form of a colorless solid from the 2-methyl-6-nitrobenzoic anhydride (MNBA)/4-dimethylaminopyridine (DMAP)-catalyzed reaction of 5-bromofuran-2-carboxylic acid and isoniazid in dichloromethane at room temperature with a yield of 83%. The structure of N′-(5-bromofuran-2-carbonyl)isonicotinohydrazide (1) was elucidated using 1H NMR, 13C NMR, FTIR, and high-resolution mass spectrometry. Molecular docking screening of the title compound (1) on cyclooxygenase-2 (COX-2) protein (PDB ID: 5IKR) indicated that compound (1) has a good binding affinity, suggesting that further structure optimization and in-depth research can be carried out on compound (1) as a potential COX-2 inhibitor.

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“…[16][17][18][19][20] In parallel, cinnamide pharmacophore is regarded an interesting scaffold in the realm of medicinal and pharmaceutical chemistry. 21 Cinnamide-based compounds also displayed a wide plethora of biological properties including anticancer activities via different mechanism of action such as the inhibition of tyrosine kinase, cell cycle arrest and so on. [22][23][24][25][26] Moreover, cinnamide moiety is commonly exploited as a potential pharmacologically active component in the construction of tubulin assembly inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and cytotoxic activity of molecular hybrids based on quinolin-8-yloxy and cinnamide hybrids and their apoptosis inducing property

Binjawhar,

Al-Salmi,

Abu Ali

et al. 2024

RSC Adv.

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Synthesis, α-glucosidase inhibitory activity, and molecular docking of cinnamamides

Cited by 5 publications

References 58 publications

A New Potent Inhibitor against α-Glucosidase Based on an In Vitro Enzymatic Synthesis Approach

A New Potent Inhibitor against α-Glucosidase Based on an In Vitro Enzymatic Synthesis Approach

N′-(5-Bromofuran-2-carbonyl)isonicotinohydrazide

Design, synthesis and cytotoxic activity of molecular hybrids based on quinolin-8-yloxy and cinnamide hybrids and their apoptosis inducing property

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