Exploration of thioxothiazolidinone–sulfonate conjugates as a new class of aldehyde/aldose reductase inhibitors: A synthetic and computational investigation

Andleeb, Hina; Tehseen, Yildiz; Jabeen, Farrukh; Khan, Imtiaz; Iqbal, Jamshed; Hameed, Shahid

doi:10.1016/j.bioorg.2017.08.009

Cited by 19 publications

(7 citation statements)

References 41 publications

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“…The organic fraction was extracted with dichloromethane (2 Â 15 ml). The combined organic fractions were dried (MgSO 4 ), filtered and concentrated in vacuo to afford the title compounds 3a-c and 4a-c (Andleeb et al, 2017). CHO), 7.89-7.81 (2H, m, ArH), 7.77 (2H, d, J = 8.8 Hz, ArH), 7.55-7.48 (2H, m, ArH), 7.20-7.13 (2H, m, ArH); 13 C NMR (101 MHz, CDCl 3 ): 190.…”

Section: Preparation Of 2-and 4-formylphenyl 4-substituted Benzenesulmentioning

confidence: 99%

“…The syntheses of the 2-and 4-formylphenyl 4-substituted benzenesulfonates 3a-c and 4a-c were accomplished by the efficient condensation of salicylaldehyde/4-hydroxybenzaldehyde (1) with different aryl sulfonyl chlorides (i.e. 2a-c) in the presence of triethylamine as a base (Scheme 1) (Andleeb et al, 2017). The IR spectra of 3a-c and 4a-c showed the stretching absorption bands at 1352-1345 and 1728-1712 cm À1 attributable to the presence of sulfonate S O and aldehyde C O groups, respectively.…”

Section: Synthesismentioning

confidence: 99%

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A comparative experimental and theoretical investigation of hydrogen-bond, halogen-bond and π–π interactions in the solid-state supramolecular assembly of 2- and 4-formylphenyl arylsulfonates

et al. 2018

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To explore the operational role of noncovalent interactions in supramolecular architectures with designed topologies, a series of solid-state structures of 2- and 4-formylphenyl 4-substituted benzenesulfonates was investigated. The compounds are 2-formylphenyl 4-methylbenzenesulfonate, CHOS, 3a, 2-formylphenyl 4-chlorobenzenesulfonate, CHClOS, 3b, 2-formylphenyl 4-bromobenzenesulfonate, CHBrOS, 3c, 4-formylphenyl 4-methylbenzenesulfonate, CHOS, 4a, 4-formylphenyl 4-chlorobenzenesulfonate, 4b, CHClOS, and 4-formylphenyl 4-bromobenzenesulfonate, CHBrOS, 4c. The title compounds were synthesized under basic conditions from salicylaldehyde/4-hydroxybenzaldehydes and various aryl sulfonyl chlorides. Remarkably, halogen-bonding interactions are found to be important to rationalize the solid-state crystal structures. In particular, the formation of O...X (X = Cl and Br) and type I X...X halogen-bonding interactions have been analyzed by means of density functional theory (DFT) calculations and characterized using Bader's theory of `atoms in molecules' and molecular electrostatic potential (MEP) surfaces, confirming the relevance and stabilizing nature of these interactions. They have been compared to antiparallel π-stacking interactions that are formed between the arylsulfonates.

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Section: Preparation Of 2-and 4-formylphenyl 4-substituted Benzenesulmentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

A comparative experimental and theoretical investigation of hydrogen-bond, halogen-bond and π–π interactions in the solid-state supramolecular assembly of 2- and 4-formylphenyl arylsulfonates

et al. 2018

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“…There were depicted that aryl sulfonate derivatives were found as potential anticancer alkylating agents [13] . Furthermore, another study described the new thioxothiazolidinone‐sulfonate compounds as potent aldehyde/aldose reductase inhibitors [14] …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Biological Activity and Molecular Docking Studies of Novel Sulfonate Derivatives Bearing Salicylaldehyde

Korkmaz

Bursal

2022

Chemistry & Biodiversity

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Enzyme activity alterations have been associated with many metabolism disorders and have crucial roles in the pathogenesis of some diseases. Tyrosinase is a key enzyme in melanin biosynthesis, which is responsible for skin pigmentation to protect the skin from solar radiation. Pancreatic lipase has been considered a key enzyme for the treatment of obesity. Herein, we reported the synthesis and enzyme inhibitions of a series of sulfonates as possible tyrosinase and pancreatic lipase inhibitors. According to the calculated IC50 values, compound 3f (74.1±11.1 μM) and compound 3c (86.6±6.9 μM) were determined to be the best inhibitors among the synthesized compounds for the tyrosinase and pancreatic lipase enzymes, respectively. The approach yielded at extremely high level by creating very flexible structural domains for the chemically modified groups. The structural characterization of the target molecules was implemented by 1H‐NMR, 13C‐NMR, and HR‐MS analyses. Also, molecular docking studies of the synthesized compounds with tyrosinase and pancreatic lipase enzymes were conducted using AutoDock Vina software. Additionally, the studies of the absorption distribution, metabolism, and excretion (ADME) were performed to uncover the target compounds′ pharmacokinetics, drug similarities, and medicinal properties of the novel sulfonate derivatives bearing salicylaldehyde.

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“…The sorbitol in turn converts metabolically via another enzyme sorbitol dehydrogenase into fructose, resulting in increase in the glucose flux. 8 High glucose level in diabetes promotes the combination of glucose to ALR2 and metabolized about one third of the total glucose to sorbitol via the polyol pathway in tissues such as retina, lens, peripheral nerves and kidneys. As a result, the regulated polyol pathway accumulates the sorbitol in cells causing swelling of cell, osmotic imbalance and changes in permeability of membrane.…”

Section: Introductionmentioning

confidence: 99%

Exploring synthetic and therapeutic prospects of new thiazoline derivatives as aldose reductase (ALR2) inhibitors

et al. 2021

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Exploration of thioxothiazolidinone–sulfonate conjugates as a new class of aldehyde/aldose reductase inhibitors: A synthetic and computational investigation

Cited by 19 publications

References 41 publications

A comparative experimental and theoretical investigation of hydrogen-bond, halogen-bond and π–π interactions in the solid-state supramolecular assembly of 2- and 4-formylphenyl arylsulfonates

A comparative experimental and theoretical investigation of hydrogen-bond, halogen-bond and π–π interactions in the solid-state supramolecular assembly of 2- and 4-formylphenyl arylsulfonates

Synthesis, Biological Activity and Molecular Docking Studies of Novel Sulfonate Derivatives Bearing Salicylaldehyde

Exploring synthetic and therapeutic prospects of new thiazoline derivatives as aldose reductase (ALR2) inhibitors

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