Synthesis, Characterization and Biological Evaluation of Novel Thiourea Derivatives

Tok, Fatih; Çakir, Cansel; Çam, Dilaycan; KIRPAT, Mustafa Murat; Sıcak, Yusuf

doi:10.33808/clinexphealthsci.1062872

Cited by 3 publications

(2 citation statements)

References 28 publications

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“…19 Furthermore, the antidiabetic activity of the synthesized thiourea derivatives has also been previously evaluated. 20,21 According to the literature, any disorder or upregulation of PTP1B in the body can cause hyperglycemia. 22 Skeletal muscles are the main targets of insulin-mediated glucose homeostasis.…”

Section: Introductionmentioning

confidence: 99%

“…A group of researchers synthesized and studied the antibacterial activities of vanadium (IV, V) complexes containing chelidamic acid and novel thiourea derivatives 19 . Furthermore, the antidiabetic activity of the synthesized thiourea derivatives has also been previously evaluated 20,21 . According to the literature, any disorder or upregulation of PTP1B in the body can cause hyperglycemia 22 .…”

Section: Introductionmentioning

confidence: 99%

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Thiourea derivatives inhibit key diabetes‐associated enzymes and advanced glycation end‐product formation as a treatment for diabetes mellitus

et al. 2022

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This study was designed to screen novel thiourea derivatives against different enzymes, such as α-amylase, α-glucosidase, protein tyrosine phosphatase 1 B, and advanced glycated end product (AGEs). A cytotoxicity analysis was performed using rat L6 myotubes and molecular docking analysis was performed to map the binding interactions between the active compounds and α-amylase and α-glucosidase. The data revealed the potency of five compounds, including Ethiourea), and AH (1-(2,4-difluorophenyl)-3-(2-iodophenyl) thiourea), showed activity against α-amylase. The corresponding percentage inhibitions were found to be 85 ± 1.9, 82 ± 0.7, 75 ± 1.2, 72 ± 0.4, and 65 ± 1.1%, respectively. These compounds were then screened using in vitro assays. Among them, AH showed the highest activity against α-glucosidase, AGEs, and PTP1B, with percentage inhibitions of 86 ± 0.4% (IC 50 = 47.9 μM), 85 ± 0.7% (IC 50 = 49.51 μM), and 85 ± 0.5% (IC 50 = 79.74 μM), respectively. Compound AH showed an increased glucose uptake at a concentration of 100 μM. Finally, an in vivo study was conducted using a streptozotocin-induced diabetic mouse model and PTP1B expression was assessed using real-time PCR. Additionally, we examined the hypoglycemic effect of compound AH in diabetic rats compared to the standard drug glibenclamide.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Thiourea derivatives inhibit key diabetes‐associated enzymes and advanced glycation end‐product formation as a treatment for diabetes mellitus

et al. 2022

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Synthesis, Characterization, Molecular Docking Studies and Biological Evaluation of Some Novel 3,5-disubstituted-1-phenyl-4,5-dihydro-1H-pyrazole Derivatives

Tok,

Bayrak,

Karakaraman

et al. 2024

COC

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In this study, some new pyrazoline derivatives bearing cyano or nitro groups were synthesized. The structures of the compounds were characterized by IR, 1H-NMR, 13C-NMR and elemental analysis data. The ABTS·+, DPPH·, CUPRAC and β-Carotene/linoleic acid assays were carried out to determine the antioxidant activity of the synthesized pyrazolines. Compound P14 showed higher antioxidant activity than the standard substance BHA with IC50 values of 1.71±0.31 μM and 0.29±0.04 μM in ABTS+ and β-carotene/linoleic acid assays, respectively. Compound P12 also exhibited higher antioxidant activities than BHA with an IC50 value of 0.36±0.14 μM in β-carotene/linoleic acid analysis. In activity studies of pyrazolines against cholinesterase (AChE and BChE), tyrosinase, α-amylase and α- glucosidase, compound P1 (IC50 = 39.51±3.80 μM) showed higher activity against α-amylase and compounds P5 and P12 displayed higher activity against α-glucosidase than acarbose with IC50 values of 14.09±0.62 and 83.26±2.57 μM, respectively. The drug-like properties such as Lipinski and Veber, bioavailability and toxicity risks of the synthesized compounds were also evaluated. The compounds were predicted to be compatible with Lipinski and Veber rules, have high bioavailability and low toxicity profiles. Moreover, molecular docking studies were performed to better understand the high activity of the compounds against a-amylase and a-glucosidase enzymes.

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Synthesis, Computational Study, and In Vitro α-Glucosidase Inhibitory Action of Thiourea Derivatives Based on 3-Aminopyridin-2(1H)-Ones

Shulgau,

Palamarchuk,

Sergazy

et al. 2024

Molecules

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Reactions with allyl-, acetyl-, and phenylisothiocyanate have been studied on the basis of 3-amino-4,6-dimethylpyridine-2(1H)-one, 3-amino-4-phenylpyridine-2-one, and 3-amino-4-(thiophene-2-yl)pyridine-2(1H)-one (benzoyl-)isothiocyanates, and the corresponding thioureide derivatives 8-11a-c were obtained. Twelve thiourea derivatives were obtained and studied for their anti-diabetic activity against the enzyme α-glucosidase in comparison with the standard drug acarbose. The comparison drug acarbose inhibits the activity of α-glucosidase at a concentration of 15 mM by 46.1% (IC50 for acarbose is 11.96 mM). According to the results of the conducted studies, it was shown that alkyl and phenyl thiourea derivatives 8,9a-c, in contrast to their acetyl–(benzoyl) derivatives and 10,11a-c, show high antidiabetic activity. Thus, 1-(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)-3-phenylthiourea 9a has the highest inhibitory activity against the enzyme α-glucosidase, exceeding the activity of the comparison drug acarbose, which inhibits the activity of α-glucosidase by 56.6% at a concentration of 15 mm (IC50 = 9,77 mM). 1-(6-methyl-2-oxo 4-(thiophen-2-yl)-1,2-dihydropyridin-3-yl)-3-phenylthiourea 9c has inhibitory activity against the enzyme α-glucosidase, comparable to the comparison drug acarbose, inhibiting the activity of α-glucosidase at a concentration of 15 mm per 41.2% (IC50 = 12,94 mM). Compounds 8a, 8b, and 9b showed inhibitory activity against the enzyme α-glucosidase, with a lower activity compared to acarbose, inhibiting the activity of α-glucosidase at a concentration of 15 mM by 23.3%, 26.9%, and 35.2%, respectively. The IC50 against α-glucosidase for compounds 8a, 8b, and 9b was found to be 16.64 mM, 19.79 mM, and 21.79 mM, respectively. The other compounds 8c, 10a, 10b, 10c, 11a, 11b, and 11c did not show inhibitory activity against α-glucosidase. Thus, the newly synthesized derivatives of thiourea based on 3-aminopyridine-2(1H)-ones are promising candidates for the further modification and study of their potential anti-diabetic activity. These positive bioanalytical results will stimulate further in-depth studies, including in vivo models.

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Synthesis, Characterization and Biological Evaluation of Novel Thiourea Derivatives

Cited by 3 publications

References 28 publications

Thiourea derivatives inhibit key diabetes‐associated enzymes and advanced glycation end‐product formation as a treatment for diabetes mellitus

Thiourea derivatives inhibit key diabetes‐associated enzymes and advanced glycation end‐product formation as a treatment for diabetes mellitus

Synthesis, Characterization, Molecular Docking Studies and Biological Evaluation of Some Novel 3,5-disubstituted-1-phenyl-4,5-dihydro-1H-pyrazole Derivatives

Synthesis, Computational Study, and In Vitro α-Glucosidase Inhibitory Action of Thiourea Derivatives Based on 3-Aminopyridin-2(1H)-Ones

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