Synthesis, characterization, molecular docking, and biological activities of coumarin–1,2,3‐triazole‐acetamide hybrid derivatives

Sepehri, Nima; Mohammadi‐Khanaposhtani, Maryam; Asemanipoor, Nafise; Hosseini, Samanesadat; Biglar, Mahmood; Larijani, Bagher; Mahdavi, Mohammad; Hamedifar, Haleh; Taslimi, Parham; Sadeghian, Nastaran; Gülçın, İlhami

doi:10.1002/ardp.202000109

Cited by 64 publications

(37 citation statements)

References 89 publications

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“…These are key components of cholinergic brain synapses and neuromuscular connections. [ 38–40 ] The main function of AChE and BChE is to catalyze the hydrolysis of the neurotransmitter ACh and nerve impulse termination at cholinergic synapses. Thus, compounds acting as cholinesterase inhibitors can be considered potential drugs in the treatment of AD, other neurological disorders, and as therapeutic agents.…”

Section: Resultsmentioning

confidence: 99%

New quinoxalin‐1,3,4‐oxadiazole derivatives: Synthesis, characterization, in vitro biological evaluations, and molecular modeling studies

Mirzazadeh

Asgari

Barzegari

et al. 2021

Archiv der Pharmazie

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A new series of quinoxalin‐1,3,4‐oxadiazole (10a–l) derivatives was synthesized and evaluated against some metabolic enzymes including human carbonic anhydrase (hCA) isoenzymes I and II (carbonic anhydrases I and II), cholinesterase (acetylcholinesterase and butyrylcholinesterase), and α‐glucosidase. Obtained data revealed that all the synthesized compounds were more potent as compared with the used standard inhibitors against studied target enzymes. Among the synthesized compounds, 4‐fluoro derivative (10f) against hCA I, 4‐chloro derivative (10i) against hCA II, 3‐fluoro derivative (10e) against acetylcholinesterase and butyrylcholinesterase, and 3‐bromo derivative (10k) against α‐glucosidase were the most potent compounds with inhibitory activity around 1.8‐ to 7.37‐fold better than standard inhibitors. Furthermore, docking studies of these compounds were performed at the active site of their target enzymes.

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Section: Resultsmentioning

confidence: 99%

New quinoxalin‐1,3,4‐oxadiazole derivatives: Synthesis, characterization, in vitro biological evaluations, and molecular modeling studies

Mirzazadeh

Asgari

Barzegari

et al. 2021

Archiv der Pharmazie

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“…This disease has two major kinds, type 2‐DM (T2DM, non‐insulin‐dependent diabetes) and type 1‐DM (T1DM, insulin‐dependent diabetes), which the most significant treatment protocols for T1DM is injectable insulin and for T2DM are oral factors like acarbose (glucose uptake reducer in the small intestine), sulfonylurea derivatives (stimulating release of insulin from the β‐cells), troglitazone (improving target cell response to insulin), metformin (insulin resistance reducer), and repaglinide (stimulating release of insulin from the β‐cells). [ 52–54 ]…”

Section: Introductionmentioning

confidence: 99%

Silver N‐heterocyclic carbene complexes bearing fluorinated benzyl group: Synthesis, characterization, crystal structure, computational studies, and inhibitory properties against some metabolic enzymes

Bal

Demirci

Şen

et al. 2021

Applied Organom Chemis

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A series of the silver N‐heterocyclic carbene (NHC) complexes have been synthesized from the reactions between benzimidazolium salts bearing fluorinated benzyl group and Ag2O via the deprotonation method. All Ag(I)NHC complexes were characterized by known spectroscopic techniques (1H nuclear magnetic resonance [NMR], 13C NMR, and Fourier transform infrared [FT‐IR]) and elemental analysis. The molecular structures of the two complexes were unambiguously elucidated through single‐crystal X‐ray diffraction analysis. Namely, X‐ray studies show that the coordination geometry around the Ag(I) atom in the case of complex 2c is revealed to be almost linear with C–Ag–Cl angle, whereas in complex 2e, it appears as a nonlinear structure. The inhibitory profiles of these new complexes are investigated on some metabolic enzymes. Representatively, the most potent complex against human carbonic anhydrase isoenzymes I and II (hCAs I and II), 2d, was 1.8 times more potent than standard inhibitor acetazolamide against hCAs I and II. On the other hand, complexes 2c and 2b as most potent compounds against both cholinesterase enzymes was around 5 and 1.6 times more potent than tacrine against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), respectively. The most active α‐glucosidase inhibitor 2d had similar activity to acarbose as a standard inhibitor. Furthermore, it confirms its in vitro studies as a result of molecular docking studies for each enzyme with (i) binding energy and inhibition constant values and (ii) the definition of the best conformation and nonbonding interactions of the related complexes (2b, 2c, and 2d) against the different target proteins.

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“…On the basis of the work of Sharpless and Medal, different copper sources such as Cu (I) [15][16][17][18][19][20], MNP@PIL-Cu [21], Cu-complex [22], Cu NPs [23], and HMS-DP-Cu(II) [24] have been tested. Moreover, in recent years, in order to synthesize triazoles, many other methods have been suggested [25][26][27]. Although these simple procedures are feasible for many reactions, they have a major drawback; when copper salts are used as a homogeneous catalyst, it faces problems such as difficult separation and recycling of the catalyst, cytotoxicity, and environmental pollution.…”

Section: Introductionmentioning

confidence: 99%

Upgraded valorization of copper (II) immobilization onto Schiff base-functionalized pectin grafted magnetic nanoparticles: A thermostable, reusable, and efficient nanocatalyst for the green synthesis of 1,2,3-triazole in pure water

Siuki¹,

Bagherzade²

2021

Preprint

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In this project, the new catalyst copper defines as Fe3O4@Pectin@(CH2)3-Acetamide-Cu(II) was successfully manufactured and fully characterized by different techniques, including FT-IR, XRD, TEM, FESEM, EDX, VSM, and ICP analysis. All results showed that copper was successfully supported on the polymer‐coated magnetic nanoparticles. One of the most important properties of a catalyst is the ability to be prepared from simple materials such as pectin that’s a biopolymer that is widely found in nature. The catalytic activity of Fe3O4@Pectin@(CH2)3-Acetamide-Cu(II) was examined in a classical, one pot, and the three-component reaction of terminal alkynes, alkyl halides, and sodium azide in water and observed, proceeding smoothly and completed in good yields and high regioselectivity. The critical potential interests of the present method include high yields, recyclability of catalyst, easy workup, using an eco-friendly solvent, and the ability to sustain a variety of functional groups, which give economical as well as ecological rewards. The capability of the nanocomposite was compared with previous works, and the nanocomposite was found more efficient, economical, and reproducible. Also, the catalyst can be easily removed from the reaction solution using an external magnet and reused for five runs without reduction in catalyst activity.

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Synthesis, characterization, molecular docking, and biological activities of coumarin–1,2,3‐triazole‐acetamide hybrid derivatives

Cited by 64 publications

References 89 publications

New quinoxalin‐1,3,4‐oxadiazole derivatives: Synthesis, characterization, in vitro biological evaluations, and molecular modeling studies

New quinoxalin‐1,3,4‐oxadiazole derivatives: Synthesis, characterization, in vitro biological evaluations, and molecular modeling studies

Silver N‐heterocyclic carbene complexes bearing fluorinated benzyl group: Synthesis, characterization, crystal structure, computational studies, and inhibitory properties against some metabolic enzymes

Upgraded valorization of copper (II) immobilization onto Schiff base-functionalized pectin grafted magnetic nanoparticles: A thermostable, reusable, and efficient nanocatalyst for the green synthesis of 1,2,3-triazole in pure water

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