Synthesis, biological evaluation and molecular docking of 3-substituted quinazoline-2,4(1H, 3H)-diones

Lumadhar, Santos-Ballardo; García-Páez, Fernando; Picos-Corrales, Lorenzo A.; Ochoa-Terán, Adrían; Bastidas, Pedro de Jesús Bastidas; Calderón-Zamora, Loranda; Guadalupe, Rendon-Maldonado; Osuna-Martínez, Ulises; Sarmiento-Sánchez, Juan I.

doi:10.1007/s12039-020-01813-1

Cited by 13 publications

(12 citation statements)

References 39 publications

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“…In an another study by Santos‐Ballarado et al ., the effects of the synthesized new quinazolinones on α‐glycosidase and α‐amylase were investigated. They reported that compounds showed moderate inhibitory effect against α‐Gly [29] . Whereas, our compounds have a much stronger inhibition profiles than the standard compound acarbose.…”

Section: Resultsmentioning

confidence: 62%

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Synthesis and Evaluation of Quinazolin‐4(3H)‐one Derivatives as Multitarget Metabolic Enzyme Inhibitors: A Biochemistry‐Oriented Drug Design

Tokalı¹,

Taslimi²,

Sadeghi

et al. 2023

ChemistrySelect

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In this study, imines bearing quinazolin‐4(3H)‐one were synthesized and their inhibitory properties were investigated against some metabolic enzymes including Acetylcholinesterase (AChE), Butyrylcholinesterase (BChE), α‐Glycosidase (α‐Gly), and human Carbonic Anhydrase I–II (hCA I–II). All compounds had inhibitory strength with Ki values in the range of 38.55±4.08–159.05±10.68 nM and 41.04±6.73–177.12±8.06 nM against hCA I and hCA‐II, respectively in comparison to the standard acetazolamide (AZA) Ki=125.15±0.78 nM (for hCA‐I) and Ki=148.75±0.92 nM (for hCA‐II). The compounds showed potent inhibitory activity against α‐Gly enzyme with IC50 value 0.34–2.28 nM (standard inhibitor acarbose (ACR): 3.18 nM). Also, these analogs had potent inhibitory strength with Ki values in the range of 4.20±0.15–26.10±2.36 nM against AChE and 1.22±0.05–16.09±0.88 nM against BChE in comparison to the standard tacrine (TAC) Ki=37.62±6.86 nM (for AChE) and Ki=26.75±5.79 nM (for BChE). Additionally, the molecular docking and molecular dynamics simulation study was carried out for the determination of ligand‐enzyme interactions. The docking scores of the most active compound were calculated as −7.31, −7.59, −6.66, −6.93 and −7.11 kcal/mol for AChE, BChE, hCA I, hCA II, and α‐Gly, respectively.

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Section: Resultsmentioning

confidence: 62%

“…They reported that compounds showed moderate inhibitory effect against α-Gly. [29] Whereas, our compounds have a much stronger inhibition profiles than the standard compound acarbose.…”

Section: Chemistryselectmentioning

confidence: 79%

Synthesis and Evaluation of Quinazolin‐4(3H)‐one Derivatives as Multitarget Metabolic Enzyme Inhibitors: A Biochemistry‐Oriented Drug Design

Tokalı¹,

Taslimi²,

Sadeghi

et al. 2023

ChemistrySelect

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“…A series of scaffold 47 with 3‐substituted quinazoline‐2,4‐dione was synthesized and tested for their biological potential as antidiabetic agents (Santos‐Ballardo et al, 2020). The 3‐propylquinazoline‐2,4(1 H ,3 H )‐dione and 3‐cyclohexylquinazoline‐2,4 (1 H ,3 H )‐dione derivatives have been demonstrated to be effective α‐amylase and α‐glucosidase inhibitors.…”

Section: Biological Actionsmentioning

confidence: 99%

A comprehensive review of recent advances in the biological activities of quinazolines

Gomaa

2022

Chem Biol Drug Des

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Quinazoline heterocycles are critical in the development of medications.Quinazoline derivatives have been intensively researched, providing a wide range of compounds with diverse biological roles. The quinazoline nucleus has garnered a lot of attention in medical chemistry in recent years. It was assumed to be a pharmacophore component in the development of physiologically interesting drugs. This review is an attempt to increase the potential of quinazoline by highlighting a wide range of advancements demonstrated by numerous derivatives of the quinazoline moiety, as well as focusing on diverse pharmacological actions of the quinazoline moiety. This review compiles recent studies on the quinazoline moiety described in the literature by researchers.

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“…A series with 3-substituted quinazoline-2,4 diones scaffolds was synthesized and evaluated for their biological activity as antidiabetic agents [69]. Synthesized compounds 3-propylquinazoline-2,4(1H,3H)-dione (a) and 3-cyclohexylquinazoline-2,4(1H,3H)-dione (b) as shown in Table 7, Compound 5, were found to have highly alpha-amylase and alphaglucosidase inhibitory activity in molecular docking studies artemia salina assay.…”

Section: Quinazoline As Antidiabetic Agentsmentioning

confidence: 99%

Recent Advances on Quinazoline Derivatives: A Potential Bioactive Scaffold in Medicinal Chemistry

et al. 2021

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This paper intended to explore and discover recent therapeutic agents in the area of medicinal chemistry for the treatment of various diseases. Heterocyclic compounds represent an important group of biologically active compounds. In the last few years, heterocyclic compounds having quinazoline moiety have drawn immense attention owing to their significant biological activities. A diverse range of molecules having quinazoline moiety are reported to show a broad range of medicinal activities like antifungal, antiviral, antidiabetic, anticancer, anti-inflammatory, antibacterial, antioxidant and other activities. This study accelerates the designing process to generate a greater number of biologically active candidates.

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Synthesis, biological evaluation and molecular docking of 3-substituted quinazoline-2,4(1H, 3H)-diones

Cited by 13 publications

References 39 publications

Synthesis and Evaluation of Quinazolin‐4(3H)‐one Derivatives as Multitarget Metabolic Enzyme Inhibitors: A Biochemistry‐Oriented Drug Design

Synthesis and Evaluation of Quinazolin‐4(3H)‐one Derivatives as Multitarget Metabolic Enzyme Inhibitors: A Biochemistry‐Oriented Drug Design

A comprehensive review of recent advances in the biological activities of quinazolines

Recent Advances on Quinazoline Derivatives: A Potential Bioactive Scaffold in Medicinal Chemistry

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