Synthesis of some novel heterocylic compounds derived from 2-[3-(4-chlorophenyl)-5-(4-methoxybenzyl)-4H-1,2,4-triazol-4-yl]acetohydrazide and investigation of their lipase and<b>α</b>-glucosidase inhibition

Bekircan, Olcay; Ülker, Serdar; Menteşe, Emre

doi:10.3109/14756366.2014.1003213

Cited by 26 publications

(12 citation statements)

References 41 publications

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“…Over recent decade, various heterocyclic-based compounds possessing α -glucosidase inhibitory activities have been found 13 – 24 . For example, several pyrimidine derivatives have shown excellent inhibition potency 25 – 28 .…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, molecular docking, and in vitro α-glucosidase inhibitory activities of novel 3-amino-2,4-diarylbenzo[4,5]imidazo[1,2-a]pyrimidines against yeast and rat α-glucosidase

Peytam

Takalloobanafshi

Saadattalab

et al. 2021

Sci Rep

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In an attempt to find novel, potent α-glucosidase inhibitors, a library of poly-substituted 3-amino-2,4-diarylbenzo[4,5]imidazo[1,2-a]pyrimidines 3a–ag have been synthesized through heating a mixture of 2-aminobenzimidazoles 1 and α-azidochalcone 2 under the mild conditions. This efficient, facile protocol has been resulted into the desirable compounds with a wide substrate scope in good to excellent yields. Afterwards, their inhibitory activities against yeast α-glucosidase enzyme were investigated. Showing IC50 values ranging from 16.4 ± 0.36 µM to 297.0 ± 1.2 µM confirmed their excellent potency to inhibit α-glucosidase which encouraged us to perform further studies on α-glucosidase enzymes obtained from rat as a mammal source. Among various synthesized 3-amino-2,4-diarylbenzo[4,5]imidazo[1,2-a]pyrimidines, compound 3k exhibited the highest potency against both Saccharomyces cerevisiae α-glucosidase (IC50 = 16.4 ± 0.36 μM) and rat small intestine α-glucosidase (IC50 = 45.0 ± 8.2 μM). Moreover, the role of amine moiety on the observed activity was studied through substituting with chlorine and hydrogen resulted into a considerable deterioration on the inhibitory activity. Kinetic study and molecular docking study have confirmed the in-vitro results.

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Section: Introductionmentioning

confidence: 99%

Design, synthesis, molecular docking, and in vitro α-glucosidase inhibitory activities of novel 3-amino-2,4-diarylbenzo[4,5]imidazo[1,2-a]pyrimidines against yeast and rat α-glucosidase

Peytam

Takalloobanafshi

Saadattalab

et al. 2021

Sci Rep

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“…In addition, N CH carbons in the 13 C-NMR were observed in the range of 145.83 to 153.34 ppm. [33] 5-(4-Chlorobenzyl)-2-undecyl-2, 4-dihydro-3H-1,2,4-triazol-3-one (4) was produced from deamination of compound 2 with NaNO 2 in hypophosphorous acid medium. Characteristic NH group signals of compound 4 were revealed at 3063 cm −1 in the IR spectrum, and 11.47 ppm in the 1 H-NMR spectrum.…”

Section: CLmentioning

confidence: 99%

Synthesis and pancreatic lipase inhibitory activities of some 1,2,4‐triazol‐5(3)‐one derivatives

Özdemir

Bekircan

Baltaş

et al. 2020

Journal of Heterocyclic Chem

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In this study, starting from 4-amino-5-(4-chlorobenzyl)-2,4-dihydro-3H-1,2, 4-triazole-3-one (1), the 4-Amino-5-(4-chlorobenzyl)-2-undecyl-2,4-dihydro-3H-1,2,4-triazol-3-one (2) was first synthesized and this compound was converted to Schiff base derivatives (3a-e). In the second step of the study, the 2-[3-(4-chlorobenzyl)-5-oxo-1-undecyl-1,5-dihydro-4H-1,2,4-triazole-4-yl]acetohydrazide (6), which was used as a key product in the synthesis of many heterocyclic compounds was synthesized in four steps, and then this compound was converted into methylidene acetohydrazide (7a-e), thiosemicarbazide (8a-e), and 1,2,4-triazole-5-thione (9a-e) derivatives. Also, in the last part of the study, 1,2,4-triazole-5-thione derivatives were changed into Mannich bases (10a-b) bearing a 4-phenylpiperazine ring. These new compounds were tested with regard to pancreatic lipase (PL) inhibition activity, and compound 3b, 3d, 7d, 8d, and 9d showed a considerable anti-lipase activity at various concentrations. The activity of compounds 7b (IC 50 = 1.45 ± 0.12 μM) was the highest in terms of IC 50 , comparable to that of orlistat, a well-known PL inhibitor used as an antiobesity drug.

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“…There are reports of several pharmacological activities of analogues and derivatives of DHPMs, such as antitumor, antiviral, anti-inflammatory, antidepressant, antimalarial and anticancer (Ramachandran et al, 2016), antioxidant, antibacterial (Stefani et al, 2006;de Vasconcelos et al, 2012;Niemirowicz-Laskowska et al, 2018), insecticidal and larvicidal (Venugopala et al, 2016), and calcium channel modulation (Kappe, 2000;Fathima et al, 2013). Recent studies indicate effective action of pyrimidine analogs in the treatment of diabetes, by reducing the enzyme α-glucosidase and delaying the absorption of glucose (Bekircan et al, 2015;Peytam et al, 2021).…”

Section: Introductionmentioning

confidence: 99%

Dihydropyrimidinones Against Multiresistant Bacteria

et al. 2022

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The increase in bacterial resistance to antimicrobials has led to high morbidity and mortality rates, posing a major public health problem, requiring the discovery of novel antimicrobial substances. The biological samples were identified as the Gram-negative bacilli Acinetobacter baumannii, Escherichia coli, Enterobacter cloacae, Klebsiella pneumoniae, Morganella morgannii, Pseudomonas aeruginosa and Serratia marcescens and the Gram-positive cocci Enterococcus faecium, and Staphylococcus aureus, all of them resistant to at least three classes of antimicrobials. The antibacterial activity of the compounds was checked in vitro by determining the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) by the broth microdilution method and plating in brain heart infusion (BHI) agar, respectively. The chemical characterization of the compounds was performed by measuring the melting point and gas chromatography coupled with mass spectrometry (GC–MS) on a Shimadzu GC–MS-QP system 2010SE. Synthetic compounds showed antimicrobial activity against Gram-positive cocci at MIC concentrations 0.16–80 μg/ml and Gram-negative bacilli at MIC concentrations 23.2–80 μg/ml. Enterococcus faecium and S. aureus had the best MIC values. The results of the cytotoxicity test indicated that the synthetic compounds showed no significant difference in three concentrations tested (5, 20, and 80 μg/ml), allowing cell viability not different from that assigned to the control, without the tested compounds. In this context, the development of DHPM derivatives brings an alternative and perspective on effectiveness of drugs as potential future antimicrobial agents.

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Synthesis of some novel heterocylic compounds derived from 2-[3-(4-chlorophenyl)-5-(4-methoxybenzyl)-4H-1,2,4-triazol-4-yl]acetohydrazide and investigation of their lipase andα-glucosidase inhibition

Cited by 26 publications

References 41 publications

Design, synthesis, molecular docking, and in vitro α-glucosidase inhibitory activities of novel 3-amino-2,4-diarylbenzo[4,5]imidazo[1,2-a]pyrimidines against yeast and rat α-glucosidase

Design, synthesis, molecular docking, and in vitro α-glucosidase inhibitory activities of novel 3-amino-2,4-diarylbenzo[4,5]imidazo[1,2-a]pyrimidines against yeast and rat α-glucosidase

Synthesis and pancreatic lipase inhibitory activities of some 1,2,4‐triazol‐5(3)‐one derivatives

Dihydropyrimidinones Against Multiresistant Bacteria

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