Synthesis, antimycobacterial activity, and acid dissociation constants of polyfunctionalized 3-[2-(pyrrolidin-1-yl)thiazole-5-carbonyl]-2H-chromen-2-one derivatives

Nural, Yahya

doi:10.1007/s00706-018-2250-7

Cited by 18 publications

(3 citation statements)

References 64 publications

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“…Acylthiourea derivatives have been intensively studied in drug research studies because of their significant bioactivity [20] and their use as intermediates in the synthesis of various pharmacophore groups such as thiazole [21] and thiohydantoin [22] . Due to the ability of acylthioureas to form hydrogen bonds, they interact strongly with the active site [23] .…”

Section: Introductionmentioning

confidence: 99%

Investigation of The Effect of Acylthiourea Derivatives on Diabetes‐Associated Enzymes

et al. 2022

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One of the most prevalent chronic metabolic disorders, diabetes mellitus, is defined by chronic hyperglycemia and the emergence of microvascular and macrovascular pathology unique to diabetes. Several diabetes problems are primarily caused by persistent hyperglycemia. In this study, aldose reductase (AR) and sorbitol dehydrogenase (SDH) enzymes were purified using chromatographic techniques from sheep kidneys and α-glycosidase purchased commercially. The inhibitory effect of seven acylthiourea compounds on the activity of these enzymes associated with diabetes was investigated. As a result of the studies, the acyl thioureas showed an inhibition effect at the micromolar level on the activity of studied enzymes. The most active compound dimethyl 1-((4-methoxybenzoyl)carbamothioyl)-5,5-diphenylpyrrolidine-2,4-dicarboxylate (2 c) had an excellent selectivity on AR with K i : 0.200 � 0.024 μM and dimethyl 1-((2,4-dichlorobenzoyl)carbamothioyl)-5,5-diphenylpyrrolidine-2,4-dicarboxylate (2 g) on SDH and αglycosidase with K i : 0.114 � 0.01 μM and K i : 055 � 0.01 μM, respectively. The findings suggest that our study will contribute to the development of innovative and/or alternative treatment strategies in the treatment of diabetes in the future since acylthiourea compounds have an effective inhibition capacity on critical enzymes associated with diabetes.

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Section: Introductionmentioning

confidence: 99%

Investigation of The Effect of Acylthiourea Derivatives on Diabetes‐Associated Enzymes

et al. 2022

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“…The acid dissociation constant (p K a ) of 1,4‐naphthoquinone acyl thiourea hybrids 1 – 7 were determined according to the method described in the literature using a computer‐controlled automated titrator having an ultra‐combination pH electrode [36] p K a values of the 1 – 7 ligands were potentiometrically determined in a DMSO‐water (20 : 80 v/v) hydro‐organic solvent in an acidic medium and 0.1 M NaCl ionic strength at 25.0±0.1 °C, and the obtained p K a values are given in Table 1. Titration curves of 1 – 7 and distribution curve of 1 are given in Figure 10, and distribution curves of 2 – 7 are presented in the SI part.…”

Section: Resultsmentioning

confidence: 99%

“…The acid dissociation constant (p K a ) is critical analytical data due to providing significant information on the acidity/basicity of compounds and their solubility in various solvents and pH mediums. It is also a useful parameter for the development of molecular docking programs, which has a very important place in drug design, and for determining optimal conditions while developing analytical methods [34–36] …”

Section: Introductionmentioning

confidence: 99%

Anti‐inflammatory Potential of 1,4‐Naphthoquinone Acyl Thiourea Hybrids on Lipopolysaccharide‐Activated Mammalian Macrophages, and Their Acid Dissociation Constants

Canatar,

Türkben,

Efeoglu

et al. 2023

ChemistrySelect

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In this study, seven new and known 1,4‐naphthoquinone acyl thiourea hybrids were synthesized and their molecular structures were confirmed by various analytical methods. These derivatives were tested for their anti‐inflammatory potential on the murine macrophages. Pro‐inflammatory cytokine production levels and cell viabilities were compared between the groups and with LPS positive control groups to determine the most potent anti‐inflammatory drug candidate. Our results suggest that these derivatives had anti‐inflammatory activity without exerting major cytotoxicity. Their future evaluation in inflammatory and autoimmune disease settings will be crucial for their possible utilization in the clinical setting. The acid dissociation constants of synthesized hybrids 1–7 were determined potentiometrically at 25.0±0.1 °C, at an ionic strength of 0.1 M NaCl in 20 % (v/v) DMSO – water hydro‐organic solvent mixture in an acidic medium. Three acid dissociation constants were calculated for each hybrid with the HYPERQUAD computer program using the data obtained as a result of potentiometric titrations under the specified conditions.

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Synthesis, Biological Evaluation, Molecular Docking, and Acid Dissociation Constant of New Bis‐1,2,3‐triazole Compounds

et al. 2021

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In this study, new bis-1,2,3-triazole derivatives, N,N'-(1,3phenylene)bis(2-(4-R-1H-1,2,3-triazol-1-yl)acetamide), were synthesized by copper-catalyzed azide-alkyne cycloaddition click chemistry in 84-96 % yield. A wide range bioactivity screening was performed to determine DNA cleavage, antioxidant, antibacterial and antifungal activities. All of the synthesized bis-1,2,3-triazoles showed excellent DNA cleavage activity and 4 e, bearing 2-bromoethyl moiety as a substituent, was almost degraded all of the plasmid DNA. Molecular docking simulations suggest that the synthesized compounds act as minor groove binders of DNA. The antioxidant activities of the bis-1,2,3-triazoles were determined based on the radical scavenging effect of the stable 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical and iron chelating activity. The compounds exhibited effective iron chelating activity at 200 mg/L while showing a moderate ability to scavenge DPPH radical. The compounds exhibited antibacterial activity against B. cereus, L. pneumophila subsp. pneumophila, S. aureus, P. aeruginosa, E. coli and E. hirae bacterial strains, and antifungal activity against C. albicans and C. tropicalis microfungus strains with a MIC value in the range of 4-128 μg/mL. 4 d, bearing cyclohexylmethyl moiety as substituent, exhibited a broadspectrum antimicrobial activity (both antibacterial and antifungal). Four different acid dissociation constant (pK a ) values of each product were determined potentiometrically in 20 % (v/v) dimethyl sulfoxide-water at 25 � 0.1°C, at an ionic background of 0.1mol/L of NaCl using the HYPERQUAD program.

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Synthesis, antimycobacterial activity, and acid dissociation constants of polyfunctionalized 3-[2-(pyrrolidin-1-yl)thiazole-5-carbonyl]-2H-chromen-2-one derivatives

Cited by 18 publications

References 64 publications

Investigation of The Effect of Acylthiourea Derivatives on Diabetes‐Associated Enzymes

Investigation of The Effect of Acylthiourea Derivatives on Diabetes‐Associated Enzymes

Anti‐inflammatory Potential of 1,4‐Naphthoquinone Acyl Thiourea Hybrids on Lipopolysaccharide‐Activated Mammalian Macrophages, and Their Acid Dissociation Constants

Synthesis, Biological Evaluation, Molecular Docking, and Acid Dissociation Constant of New Bis‐1,2,3‐triazole Compounds

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