Publication: Synthesis Of Carboxamidostilbene Analogues Via Heck-Cross Coupling Reaction, In Silico And Antidiabetes Evaluation
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Date
2025-02
Authors
Babai, Mahdi
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Abstract
New series of ortho-carboxamidostilbene and para-carboxamidostilbene derivatives were synthesised via the heck coupling reaction. The structures of the synthesised compounds were confirmed by various spectroscopic analyses, including ftir, hresims, 1d-nmr (1h nmr and 13c nmr), 2d-nmr (cosy and hmbc). Carboxamidostilbenes were synthesised by reacting iodophenyl acylamide in dry dmf with styrene and et3n as the base in the presence of palladium (ii) acetate (pd(oac)2). All carboxamidostilbenes were screened in vitro for their α-amylase inhibition properties, using resveratrol and acarbose as referenced drugs. The compounds exhibited moderate to good inhibitory activity, with ic50 values ranging from 13.3 to 28.2 μm, compared to resveratrol and acarbose (ic50 = 35.0 ± 3.5, 30.2 ± 0.1 μm, respectively). Among them, compounds 186e, 186f, 187e, 191d, 191e, 191f, 192c, 192d, 192e and 192f showed significant α-amylase inhibitory activity, with ic50 values between 13.3 and 27.9 μm. Structure-activity relationship (sar) analysis was performed to establish the relationship between chemical structure and α-amylase inhibitory activity. In silico molecular docking was used to model the binding interactions of the ortho- and para-carboxamidostilbenes with α-amylase. Pharmacokinetic properties (adme) and drug-likeness were also investigated. Molecular docking studies showed strong interactions between the investigated molecules and the α-amylase binding pocket.
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Amides—Synthesis