17385-68-1Relevant articles and documents
A Library of Thiazolidin-4-one Derivatives as Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitors: An Attempt To Discover Novel Antidiabetic Agents
Patel, Ashish D.,Pasha, Thopallada Y.,Lunagariya, Paras,Shah, Umang,Bhambharoliya, Tushar,Tripathi, Rati K. P.
, p. 1229 - 1242 (2020)
Protein tyrosine phosphatase 1B (PTP1B) is an important target for the treatment of diabetes. A series of thiazolidin-4-one derivatives 8–22 was designed, synthesized and investigated as PTP1B inhibitors. The new molecules inhibited PTP1B with IC50 values in the micromolar range. 5-(Furan-2-ylmethylene)-2-(4-nitrophenylimino)thiazolidin-4-one (17) exhibited potency with a competitive type of enzyme inhibition. structure–activity relationship studies revealed various structural facets important for the potency of these analogues. The findings revealed a requirement for a nitro group-including hydrophobic heteroaryl ring for PTP1B inhibition. Molecular docking studies afforded good correlation with experimental results. H-bonding and π–π interactions were responsible for optimal binding and effective stabilization of virtual protein-ligand complexes. Furthermore, in-silico pharmacokinetic properties of test compounds predicted their drug-like characteristics for potential oral use as antidiabetic agents.Additionally, a binding site model demonstrating crucial pharmacophoric characteristics influencing potency and binding affinity of inhibitors has been proposed, which can be employed in the design of future potential PTP1B inhibitors.
Synthesis of novel inhibitors of α-amylase based on the thiazolidine-4-one skeleton containing a pyrazole moiety and their configurational studies
Kumar, Parvin,Duhan, Meenakshi,Kadyan, Kulbir,Sindhu, Jayant,Kumar, Sunil,Sharma, Hitender
, p. 1468 - 1476 (2017)
Postprandial hyperglycemia can be controlled by delaying the absorption of glucose resulting from carbohydrate digestion. α-Amylase is the initiator of the hydrolysis of polysaccharides, and therefore developing α-amylase inhibitors can lead to development of new treatments for metabolic disorders like diabetes mellitus. In the present work, we set out to rationally develop α-amylase inhibitors based on the thiazolidine-4-one scaffold. The structures of all these newly synthesized hybrids were confirmed by spectroscopic analysis (IR, 1H-NMR, MS). The appearance of two sets of signals for some protons in 1H NMR revealed the existence of a mixture of 2E,5Z (37.1-42.0%) and 2Z,5Z isomers (58.4-62.8%), which was further supported by DFT studies. All the newly synthesized compounds have potential inhibitory properties as revealed through in vitro α-amylase inhibition activity. Compound 5a at 100 μg mL-1 concentration showed a remarkable inhibition of 90.04%. In vitro α-amylase inhibition was further supported by docking studies of compound 5a against the active site of human pancreatic α-amylase (PDB ID: 2QV4). The docking studies revealed that the bonding interactions found between 5a and human pancreatic α-amylase are similar to those responsible for α-amylase inhibition by acarbose.
Synthesis and exploration of configurational dynamics in equilibrating E/Z 2-aryliminothiazolidin-4-ones using NMR and estimation of thermodynamic parameters
Devi, Meena,Kumar, Parvin,Sindhu, Jayant,Singh, Rahul
, p. 5012 - 5025 (2022/04/07)
In the present study, 2-aryliminothiazolidin-4-ones (3 and 5) were utilized as dynamic chemical systems, whose different states are modulated in a reversible fashion through specific chemical stimuli. The in-depth NMR investigation revealed that the magnitude of rotational energy barrier (ΔG?) is affected markedly by (1) the solvent polarity; (2) the electronic nature of the ring system present on the exocyclic CQN bond and (3) the temperature of the system. The derivatives of 5-(3-arylallylidene)-2-(arylimino)thiazolidin-4-one exist in two isomeric forms at room temperature in DMSO-d6: (2E,5Z,7E) ? (2Z,5Z,7E). The stereodynamics of the synthesized derivatives (5a-5t) has been investigated using variable temperature dynamic 1H-NMR (VT DNMR). The ΔG? values (≈15 kcal mol?1) estimated for the dynamic process depict a significant barrier between two forms in solution at ambient temperature. To go a step further, line shape analysis was also performed to get a clear understanding of the equilibration mechanism.
New thiazolidinyl analogs containing pyridine ring: Synthesis, biological evaluation and QSAR studies
Ranga, Reetu,Sharma, Vikas,Kumar, Vipin
, p. 1538 - 1548 (2013/07/26)
A series of pyridine derivatives of thiazolidin-4-ones (4a-4o) has been synthesized. Structures of these compounds were established on the basis of elemental analysis, IR, 1H NMR, 13C NMR, and Mass spectral data. All the synthesized compounds have been evaluated for their anti-inflammatory and analgesic effects. The results showed that compound 2-[4-methylphenylimino]-5-(1H-pyridin-2-ylmethylidene)-1,3-thiazolidin-4-one (4d), 2-(2,4-dinitro-phenylhydrazinylidine)-5-(1H-pyridin-2-yl-methylidene)-1,3- thiazolidin-4-one (4h), and 2-[3-nitro-phenylimino]-5-(1H-pyridin-2-yl- methylidene)-1,3-thiazolidin-4-one (4j) exhibited good anti-inflammatory and analgesic activity. Compound 4h was found to be the most active compound of the series with an interesting dual anti-inflammatory and analgesic activity. Docking simulation was performed to position synthesized compounds into the active site of COX-2. The relationships of energy-based docking score with analgesic and anti-inflammatory activities were also investigated by linear regression method. The QSAR models with R 2 of 0.621 and 0.740 were developed for analgesic and anti-inflammatory activities, respectively.
