Synthesis, Characterization, ADMET prediction, and Molecular Docking Studies of Novel Coumarin Sulfonate Derivatives

Korkmaz, Adem

doi:10.21597/jist.1089701

Cited by 7 publications

(10 citation statements)

References 32 publications

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“…Benzothiazole‐sulfonate hybrid derivatives containing azomethine motif were modeled and their inhibition against pancreatic lipase was evaluated by in vitro and in silico methods. Target molecules were synthesized using procedures similar to our previous work [21–24] . In addition, the aromatic ring backbones of the sulfonate groups are decorated with 2,4,5‐trichloro, 2,4,6‐trimethyl, 4‐methyl, 2‐methyl‐5‐nitro, 4‐bromo, 4‐methoxy, 4‐fluoro, and 4‐chloro substituents.…”

Section: Resultsmentioning

confidence: 99%

“…Benzothiazole-sulfonate hybrid bearing azomethine compounds were synthesized by the method [21][22][23][24] previously studied by our group. Compound 3 (1 mmol) and triethylamine (1.2 mmol) were placed in a 50 mL flask.…”

Section: General Synthesis Of Benzothiazole-sulfonate Hybrid Bearing ...mentioning

confidence: 99%

“…Target molecules were synthesized using procedures similar to our previous work. [21][22][23][24] In addition, the aromatic ring backbones of the sulfonate groups are decorated with 2,4,5-trichloro, 2,4,6trimethyl, 4-methyl, 2-methyl-5-nitro, 4-bromo, 4-methoxy, 4fluoro, and 4-chloro substituents. Benzothiazole-sulfonate hybrid derivatives containing the azomethine motif were synthesized in 70 min using a TEA-Base/substrate ratio of 1.2 at 0-5 °C.…”

Section: Synthesismentioning

confidence: 99%

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In Silico and in Vitro Biological Evaluation of Novel Serial Sulfonate Derivatives on Pancreatic Lipase Activity

Yetişsin,

Korkmaz,

Kaya

2023

Chemistry & Biodiversity

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The novel benzothiazole sulfonate hybrid derivatives containing azomethine group were synthesized and characterized using 1H NMR, 13C NMR, and HRMS analysis. The potential enzyme inhibition activities against pancreatic lipase of the novel benzothiazole sulfonate hybrid derivatives containing azomethine group were screened with in vitro and in silico methods. IC50 values of compounds 5b (23.89 µM), 5i (28.87 µM), and 5f (30.13±4.32) were found to be more effective pancreatic lipase inhibitors than orlistat (57.75 µM) in vitro studies. Also, the binding affinities of compounds 5b (‐8.7 kcal/mol), 5i (‐8.6 kcal/mol), and 5f (‐8.9 kcal/mol) were found potential inhibitors for pancreatic lipase in silico studies. In addition, the absorption distribution, metabolism, and excretion properties (ADME), molecular properties, toxicity estimation, and bioactivity scores of the synthesized compounds were scanned. It was found to have the ability to cross the brain‐blood barrier for compounds 5a, 5b, 5c, and 5d. All compounds were calculated to be taken orally as drugs, suitable for absorption in the intestinal tract and not carcinogenic, as well as very strongly bound to plasma proteins. Finally, compound 5f was observed to be the best inhibitor for pancreatic lipase according to in vitro and in silico studies.

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Section: Resultsmentioning

confidence: 99%

Section: General Synthesis Of Benzothiazole-sulfonate Hybrid Bearing ...mentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

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In Silico and in Vitro Biological Evaluation of Novel Serial Sulfonate Derivatives on Pancreatic Lipase Activity

Yetişsin,

Korkmaz,

Kaya

2023

Chemistry & Biodiversity

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“…The benzothiazole-sulfonate hybrid derivatives (3 a-i) were prepared similarly to the source method. [48][49][50] The 2-hydroxybenzothiazole (0.517 g; 3.425 mmol) and triethylamine (3.425 mmol, 0.477 mL) were added into a 100 mL cruet and N,N-Dimethylformamide (DMF, 2 mL) was added with stirring in an ice bath. The corresponding sulfonyl chloride (3.425 mmol) was added slowly in portions over 3 minutes.…”

Section: General Synthesis Of Benzothiazole-sulfonate Hybrid Derivati...mentioning

confidence: 99%

“…The molecular docking studies for the benzothiazole-sulfonate hybrid derivatives (3 a-i) was executed in line with protocols previously established. [30,[48][49][50] The target proteins for our docking studies were sourced from the Protein Data Bank. Our molecular docking procedures employed AutoDock Vina for the primary docking simulations.…”

Section: Molecular Docking Studiesmentioning

confidence: 99%

In Vitro and In Silico Evaluation of Amylase, Tyrosinase, and Pancreatic Lipase Inhibitions of Novel Benzothiazole‐Sulfonate Derivatives

Korkmaz,

Bursal,

Kurtay

2023

ChemistrySelect

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This paper provides a comprehensive account of the synthesis and assessment of newly developed aryl sulfonate derivatives based on benzothiazole as enzyme inhibitors, specifically focusing on their ability to target tyrosinase, amylase, and pancreatic lipase. The assessments were performed utilizing experimental (in vitro) and computational (in silico) methodologies. For this aim, nine different aryl sulfonate derivatives were synthesized. The synthesized compounds were subjected to structural characterizations by utilizing Nuclear Magnetic Resonance (1H NMR, 13C NMR) and High‐Resolution Mass Spectrometry (HRMS) studies, which provided confirmation of their structural properties. The inhibitory efficiency of the compounds was determined by measuring their 50 % inhibitory concentration (IC50) values and comparing them with the standard inhibitory compounds. According to the in vitro amylase activity, benzo[d]thiazol‐2‐yl 4‐methylbenzenesulfonate showed the best inhibition with the lowest IC50 value (43.31±4.3 μM) which was calculated to be at a close level to the IC50 value of standard acarbose (38.50±3.8 μM). Also, benzo[d]thiazol‐2‐yl 4‐bromobenzenesulfonate (22.73±4.15 μM) and benzo[d]thiazol‐2‐yl 4‐chlorobenzenesulfonate (25.28±1.95 μM) were calculated to have the lowest IC50 values and the most effective inhibition capacities against pancreatic lipase. Benzo[d]thiazol‐2‐yl 4‐fluorobenzenesulfonate and benzo[d]thiazol‐2‐yl 4‐methylbenzenesulfonate significantly exhibited superior tyrosinase inhibition compared to other derivatives and conventional kojic acid. In silico molecular docking affirmed that benzo[d]thiazol‐2‐yl naphthalene‐2‐sulfonate presented the highest binding affinities to the studied enzymes, with values of −7.8 kcal/mol for tyrosinase, −10.7 kcal/mol for pancreatic lipase, and −9.4 kcal/mol for α‐amylase. The pharmacokinetic characteristics and drug‐likeness of the synthesized sulfonate derivatives were also evaluated using absorption, distribution, metabolism, excretion, and toxicity (ADMET) prediction. Density Functional Theory (DFT) calculations were employed at the DFT/B3LYP/6‐311 g(d,p) level of theory to investigate the electronic characteristics of the compounds, therefore facilitating the comprehension of the reported enzyme inhibitory actions. In summary, our research highlights the potential of benzothiazole aryl sulfonate derivatives as effective enzyme inhibitors that hold promise for therapeutic applications.

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Design, Synthesis, Characterization, Enzyme Inhibition, Molecular Docking, and Pharmacological Evaluation of New Chalcone‐Sulfonate Derivatives Bearing Thiophene

Aslan,

Yetişsin,

Korkmaz

et al. 2024

ChemistrySelect

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The novel chalcone‐sulfonate derivatives bearing thiophene motif were synthesized and characterized using 1H NMR, 13C NMR, and HRMS analysis. The evaluation of in vitro and in silico potential pancreatic lipase inhibition activity of the novel chalcone‐sulfonate derivatives bearing thiophene motif was scanned. IC50 values of compounds 5 i (28.76±2.11 μM) and 5 f (30.58±0.45 μM) were determined to be more effective pancreatic lipase inhibitors for in vitro studies. The best potential inhibitor for pancreatic lipase binding affinity was found as compound 5 f (−9.8 kcal mol−1) for in silico studies. Although compounds 5 f and 5 i were identified as the best pancreatic lipase inhibitor candidates in vitro and molecular docking studies, compounds 5 f and 5 i were predicted mutagenic and carcinogenic properties in mice according to ADMET studies. Deeply, compound 5 h was a more effective pancreatic lipase inhibitor according to enzyme inhibition, molecular docking, and ADMET studies. It can be said that compound 5 h may be a more efficient drug candidate than orlistat in the treatment of obesity.

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Synthesis, Characterization, ADMET prediction, and Molecular Docking Studies of Novel Coumarin Sulfonate Derivatives

Cited by 7 publications

References 32 publications

In Silico and in Vitro Biological Evaluation of Novel Serial Sulfonate Derivatives on Pancreatic Lipase Activity

In Silico and in Vitro Biological Evaluation of Novel Serial Sulfonate Derivatives on Pancreatic Lipase Activity

In Vitro and In Silico Evaluation of Amylase, Tyrosinase, and Pancreatic Lipase Inhibitions of Novel Benzothiazole‐Sulfonate Derivatives

Design, Synthesis, Characterization, Enzyme Inhibition, Molecular Docking, and Pharmacological Evaluation of New Chalcone‐Sulfonate Derivatives Bearing Thiophene

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