An<i>in silico</i>ADMET, molecular docking study and microwave-assisted synthesis of new phosphorylated derivatives of thiazolidinedione as potential anti-diabetic agents

Addanki, Hanumantha Rao; Vallabhaneni, Madhava Rao; Chennamsett, Subramanyam; Pullagura, Priyadarshini; Sagurthi, Someswar Rao

doi:10.1080/00397911.2021.2024574

Cited by 9 publications

(4 citation statements)

References 49 publications

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“…IC 50 values were calculated by graph pad prism® software, and the following formula calculated percentage inhibition: Pharmacokinetic properties. ADME (Distribution, Excretion, Metabolism, and Absorption) properties of synthesized compounds 9a-9c were calculated using Swiss ADME tools [23,24]. Molecular docking studies were performed to explain the binding mode and interactions of the binding site.…”

Section: Methodsmentioning

confidence: 99%

Mechanochemical Synthesis of Thiazolidinone-Triazoles Derivatives as Antidiabetic Agents: Pharmacokinetics, Molecular Docking, and In Vitro Antidiabetic Properties

et al. 2023

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Mechanochemistry is an eco-friendly and solventless method. In the present study, the surface of a custom-made closed mortar and pestle is used as a catalyst to synthesize thiazolidinone-triazole derivatives successfully. The compounds were subjected to potential antidiabetic activity. The results showed that para-chlorosubstituted derivative (9c) is most active with IC 50 values of 10±1.56. All three compounds 9a-9c with a maximum of 20% inhibition for ALR1 represent superior selectivity toward the targeted ALR2 to act as a lead in the search for new antidiabetic agents.

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Section: Methodsmentioning

confidence: 99%

Mechanochemical Synthesis of Thiazolidinone-Triazoles Derivatives as Antidiabetic Agents: Pharmacokinetics, Molecular Docking, and In Vitro Antidiabetic Properties

et al. 2023

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“…However, to our surprise, symmetric N-phosphorylated glycine or proline methyl esters have not yet been described in the literature. Nevertheless, N-phosphorylations of amino acid residues in the literature have been reported in mediocre to good yields [31][32][33][34]. These novel products can be accessed from commercially available diethyl phosphorochloridate 14a, with the corresponding N-phosphonylated glycine methyl ester (15a, 95% yield), L-homoserine lactone (15b, 89% yield) and L-proline methyl ester (15c, 88% yield) being isolated in excellent yields (Scheme 9A).…”

Section: Application For the Use Of Phosphoryl Chloridesmentioning

confidence: 99%

Synthesis of Mixed Phosphonate Esters and Amino Acid-Based Phosphonamidates, and Their Screening as Herbicides

Backx,

Desmedt,

Dejaegere

et al. 2024

IJMS

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While organophosphorus chemistry is gaining attention in a variety of fields, the synthesis of the phosphorus derivatives of amino acids remains a challenging task. Previously reported methods require the deprotonation of the nucleophile, complex reagents or hydrolysis of the phosphonate ester. In this paper, we demonstrate how to avoid these issues by employing phosphonylaminium salts for the synthesis of novel mixed n-alkylphosphonate diesters or amino acid-derived n-alkylphosphonamidates. We successfully applied this methodology for the synthesis of novel N-acyl homoserine lactone analogues with varying alkyl chains and ester groups in the phosphorus moiety. Finally, we developed a rapid, quantitative and high-throughput bioassay to screen a selection of these compounds for their herbicidal activity. Together, these results will aid future research in phosphorus chemistry, agrochemistry and the synthesis of bioactive targets.

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“…Docking studies revealed the potential interaction of compound 11 i within the active site of α-amylase (PDB ID: 7TAA, Aspergillus oryzae). The compound 11 i formed significant bonding with amino acids GLN 35 , TYR 79 , TRP 83 , and HIS 210 . Compound 11 i formed conventional hydrogen bonding with GLU 276 and ASP 349 within the active site of the α-glucosidase enzyme.…”

Section: Thiazolidinone Based α-Amylase Inhibitorsmentioning

confidence: 99%

“…SAR studies suggested the positive impact of the presence of electron-donating groups on inhibitory potential than electron-negative groups (Figure 30). Phosphorylated thiazolidinedione derivatives 26 a-j were synthesized by Addanki and coauthors [83] and tested for their in vitro inhibitory potential against the α-amylase enzyme. Results demonstrated that compounds 26 j, 26 e, 26 b and 26 f were found to show significant inhibition with IC 50 values in the range of 113.1-119.6 μg/mL in comparison to the standard drug, Acarbose (IC 50 = 110.5 μg/mL).…”

Section: Thiazolidinone Based α-Amylase Inhibitorsmentioning

confidence: 99%

α‐Amylase Inhibitors Based on Thiazolidinone Skeleton: A Promising Approach in Diabetes Management

Singh,

Sindhu,

Kumar

et al. 2023

ChemistrySelect

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Thiazolidinone scaffold has become a promising scaffold when it comes to therapeutic importance, and researchers are quite interested in it because of its wide range of applications in the different fields of chemistry. The capacity of this nucleus to interact with a variety of biological targets, including the peroxisome proliferator‐activated receptor (PPAR), protein tyrosine phosphatase 1B, aldose reductase, α‐glucosidase, and α‐amylase, has led to the observation of its antidiabetic effect. α‐Amylase (α‐1,4‐glucan‐4‐glucanohydrolase, EC 3.2.1.1) is one of the most important industrial endoamylases capable of hydrolyzing the internal α‐1,4‐glycosidic bonds in polysaccharides with net retention of α‐anomeric configuration in low molecular weight products, such as glucose, maltose, and maltotriose units. The inhibitors of α‐amylase have the ability to lower endogenous activity, which is crucial for the management of agricultural pests as well as the treatment and prevention of human disorders. In the present review, we attempted to compile the most recent studies on thiazolidinone‐based α‐amylase inhibitors, investigate their therapeutic potential in treating diabetes, comprehend the relationships between structure and activity, offer suggestions for future research and translation of these findings into clinical applications. This comprehensive review strives to be a valuable resource for researchers, medicinal chemists, and healthcare professionals involved in developing and applying novel therapeutics for treating metabolic disorders.

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Anin silicoADMET, molecular docking study and microwave-assisted synthesis of new phosphorylated derivatives of thiazolidinedione as potential anti-diabetic agents

Cited by 9 publications

References 49 publications

Mechanochemical Synthesis of Thiazolidinone-Triazoles Derivatives as Antidiabetic Agents: Pharmacokinetics, Molecular Docking, and In Vitro Antidiabetic Properties

Mechanochemical Synthesis of Thiazolidinone-Triazoles Derivatives as Antidiabetic Agents: Pharmacokinetics, Molecular Docking, and In Vitro Antidiabetic Properties

Synthesis of Mixed Phosphonate Esters and Amino Acid-Based Phosphonamidates, and Their Screening as Herbicides

α‐Amylase Inhibitors Based on Thiazolidinone Skeleton: A Promising Approach in Diabetes Management

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