A Brief Review on Different Reactions of Rhodanine DOI
Paramita Das, Suman Ray

Journal of Heterocyclic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 23, 2024

ABSTRACT 2‐Thioxo‐4‐thiazolidinone which is trivially known as rhodanine a five‐membered heterocycle, containing sulfur and nitrogen atom at 1 3 positions, respectively. It very attractive class of compounds, because derivatization yields number molecules having multifarious application in medicinal chemistry biology. There are many derived from already being used commercially drug molecules. So owing to the importance field biology, comprehensive review familiarizing different derivatives parent molecule their syntheses highly warranted. In this review, we have broadly categorized reactions as; (a) Knoevenagel condensation through C‐5 active methylene group with carbonyl (b) nucleophilic attack on thioxo position 2 by aliphatic amines, (c) oxo conversion, (d) all other reactions. far, best our knowledge, no such literature accounts for kinds reported. Here, not only presented schemes various literatures, but discussed about advantages inadequacies that particular catalytic processes. Moreover, end article given own critical analysis these reports, based understanding experience.

Language: Английский

Significance of Five-Membered Heterocycles in Human Histone Deacetylase Inhibitors DOI Creative Commons

Anton Frühauf,

Martin Behringer,

Franz‐Josef Meyer‐Almes

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(15), P. 5686 - 5686

Published: July 27, 2023

Five-membered heteroaromatic rings, in particular, have gained prominence medicinal chemistry as they offer enhanced metabolic stability, solubility and bioavailability, crucial factors developing effective drugs. The unique physicochemical properties biological effects of five-membered heterocycles positioned them key structural motifs numerous clinically Hence, the exploration five-ring remains an important research area chemistry, with aim discovering new therapeutic agents for various diseases. This review addresses incorporation heteroatoms such nitrogen, oxygen sulfur into aromatic ring these heterocyclic compounds, enhancing their polarity facilitating both stacking interactions formation hydrogen bonds. Histone deacetylases are present multiprotein complexes within epigenetic machinery play a central role cellular processes. They emerged targets cancer, neurodegenerative diseases other indications. In histone deacetylase inhibitors (HDACi's), perform functions zinc-binding group, linker or head contributing to binding activity selective recognition. focuses on providing up-to-date overview different utilized HDACi motifs, highlighting properties. It summarizes relevant publications from past decade, offering insights recent advancements this field research.

Language: Английский

Citations

16
Design, synthesis, bioassay, and in silico studies of thiazolidinedione–morpholine hybrid ionic liquids as new antidiabetic agents DOI
Somayeh Behrouz, Mohammad Navid Soltani Rad,

Zohreh Miralaei

et al.

Journal of Molecular Liquids, Journal Year: 2025, Volume and Issue: unknown, P. 127050 - 127050

Published: Jan. 1, 2025

Language: Английский

Citations

0
Facile synthesis, antimicrobial activity, and molecular docking analysis of 8-hydroxyquinoline-4-thiazolidinone hybrids DOI

Jagruti Peddapaka,

Aayesha Nasreen,

Tulja Sanam

et al.

Future Medicinal Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 13

Published: Feb. 14, 2025

8-Hydroxyquinoline and 4-thiazolidinone derivatives are promising antimicrobial agents, recognized for their activity against resistant pathogens. The aim of this study is to develop 8-hydroxyquinoline-4-thiazolidinone as potential agents. Using a one-pot reaction with sodium tetrafluoroborate an efficient eco-friendly catalyst, compounds 6a - l were synthesized subsequently screened antibacterial antifungal activity. Additionally, molecular docking dynamic simulations performed evaluate the active gain deeper insights into Compounds 6f 6 g showed superior ciprofloxacin, particularly Gram-negative bacteria, while 6b, g, h demonstrated strong effects. Molecular docking, dynamics simulations, MM-GBSA calculations highlighted binding interactions stable conformations within pocket FabZ enzyme. ADMET analyses further indicated that these possess favorable drug-like properties. hybrids exhibit broad-spectrum agents merit investigation drug candidates.

Language: Английский

Citations

0
Innovative Multitarget Organoselenium Hybrids With Apoptotic and Anti‐Inflammatory Properties Acting as JAK1/STAT3 Suppressors DOI Open Access
Saad Shaaban,

Aya Yaseen Mahmood Alabdali,

Mai H. A. Mousa

et al.

Drug Development Research, Journal Year: 2025, Volume and Issue: 86(2)

Published: March 18, 2025

ABSTRACT Herein, we report the design, synthesis, and characterization of novel organoselenium (OSe) hybrids ( 5 – 19 ) via modifications lead, N ‐(4‐selaneylphenyl)‐2‐selaneylacetamide. The OSe‐based thiazol 9 showed highest growth inhibition % (GI%) 64.72% relative to positive reference doxorubicin (DOX), with a GI% 79.5%. Furthermore, OSe derivatives low values compared normal cell lines employed, demonstrating their selectivity. tethered ‐chloroacetamide Schiff base cytotoxic effect an IC 50 (25.07 11.61 µM), respectively, against A549 tumor line (34.22 20.12 HELA cancer line. Enzyme‐linked immunosorbent assay study JAK1 STAT3 inhibitory potentials compounds in cells both promising activities 25.07 µM, respectively. Protein expression analysis on upregulation P53, BAX, Caspases 3, 6, 8, as apoptotic proteins. However, candidates expressed downregulation antiapoptotic proteins (BCL2, MMP2, MMP9). Moreover, described examined inflammatory proteins: COX2, IL‐6, IL‐1β. In addition, compound potential cycle arrest at G0, S, G2‐M layers, increase cellular levels. Finally, molecular docking studies most toward target receptors, binding scores interactions exceeding that cocrystallized inhibitor JAK1.

Language: Английский

Citations

0
Design, and synthesis of 2,4-thiazolidinedione substituted 1–3-5-triazine derivatives as anti-HIV agent via inhibition of reverse transcriptase along with anti-SARS CoV-2, antibacterial and antibiofilm activity DOI

Saumya Singh,

Kumar Saurabh Srivastava, Prashant Gahtori

et al.

Bioorganic Chemistry, Journal Year: 2025, Volume and Issue: 160, P. 108427 - 108427

Published: April 2, 2025

Language: Английский

Citations

0
Thiazolidinedione an auspicious scaffold as PPAR-γ agonist: its possible mechanism to Manoeuvre against insulin resistant diabetes mellitus DOI Creative Commons
Sourav Basak, Anjali Murmu, Balaji Wamanrao Matore

et al.

European Journal of Medicinal Chemistry Reports, Journal Year: 2024, Volume and Issue: 11, P. 100160 - 100160

Published: April 21, 2024

Thiazolidinedione (TZD) plays a crucial role in activating PPAR-γ receptor, which helps to inhibit insulin-resistant Diabetes Mellitus through binding with DNA by forming complex retinoid receptors. TZD derivatives are the sulphur and nitrogen containing heterocyclic compounds that have massive impact synthetic chemistry for their plethora of pharmacological activities. improve insulin resistance lowering blood glucose level oxidation carbohydrate case type II Mellitus. scaffold is pentacyclic sulphur-containing compound two carbonyl groups an alpha hydrogen offering huge possibility structural modification this biologically active molecule, here N-3 & C-5 positions most versatile site nucleus. In review, we focus on brief description its antidiabetic activity mechanism action, structure relationship various approach main pharmacophore hope it will help develop idea about moiety future researchers.

Language: Английский

Citations

3
Synthesis, Characterization, Antiglycation Evaluation, Molecular Docking, and ADMET Studies of 4-Thiazolidinone Derivatives DOI Creative Commons
Ashanul Haque, Mohd Wajid Ali Khan, Khalaf M. Alenezi

et al.

ACS Omega, Journal Year: 2023, Volume and Issue: 9(1), P. 1810 - 1820

Published: Dec. 28, 2023

The design and development of new small-molecule glycation inhibitors are essential for preventing various chronic diseases, including diabetes mellitus, immunoinflammation, cardiovascular, neurodegenerative diseases. 4-Thiazolidinone or thiazolidine-4-one is a well-known heterocyclic compound with the potential to inhibit formation advanced end products. In present work, we report synthesis characterization four 5-arylidene 3-cyclopropyl-2-(phenylimino)thiazolidin-4-one (1–4) compounds their human serum albumin inhibitory activity. One 5-(2H-1,3-benzodioxol-5-ylmethylidene)-3-cyclopropyl-2-(phenylimino)-1,3-thiazolidin-4-one (3) showed potent inhibition in initial, intermediary, final products reactions. Besides, conformational changes α-helix β-sheet (due hyperglycemia) were also found be reversed upon addition (3). Experimental findings complemented by computational [molecular docking, ADME/Tox, density functional theory (DFT)] studies. docking scores order 1 > 3 2 4, indicating importance polar group at moiety. results ADME/Tox DFT calculations revealed safe nature high drug-likeness stability. Overall, speculate that this study could provide valuable insights into biological activity 4-thiazolidinones.

Language: Английский

Citations

6
L‐proline‐based DES in Knoevenagel synthesis of arylidene rhodanines, thiazolidine‐2,4‐diones, and barbituric derivatives DOI
Stéphanie Hesse, Jasmine Hertzog, Sandrine Rup‐Jacques

et al.

Journal of Heterocyclic Chemistry, Journal Year: 2024, Volume and Issue: 61(6), P. 1015 - 1023

Published: April 9, 2024

Abstract Deep eutectic solvents (DES) are environmentally friendly that prevent the use of toxic organic and have been extensively studied in recent years. However, volatile compounds (VOC) often still used during workup isolation products. Here, a zero‐VOC strategy for Knoevenagel reaction is reported. (Hetero)aromatic aldehydes successfully condensed with rhodanine, thiazolidine‐2,4‐dione TZD, or barbituric acid under mild conditions an L‐proline‐based DES pure obtained after hydrolysis without any purification. For less reactive activation by microwave allows diminution time from 24 h to just 1 h.

Language: Английский

Citations

2
The synthesis and antitumor activity of novel 1-alkyl-3-phenyland 3-alkyl-1-phenylimidazothiazolotriazines DOI
Alexei N. Izmest’ev,

Sergey S. Isakov,

Ангелина Н. Кравченко

et al.

Chemistry of Heterocyclic Compounds, Journal Year: 2024, Volume and Issue: 60(3-4), P. 196 - 204

Published: April 1, 2024

Language: Английский

Citations

1
In silico evaluation of 4-thiazolidinone-based inhibitors against the receptor for advanced glycation end products (RAGE) DOI
Ashanul Haque, Khalaf M. Alenezi, Mohd Wajid Ali Khan

et al.

Journal of Biomolecular Structure and Dynamics, Journal Year: 2023, Volume and Issue: unknown, P. 1 - 12

Published: Dec. 8, 2023

Non-enzymatic glycation of biomolecules by reducing sugars led to several products, including the advanced end products (AGEs), accumulation which has been linked various life-threatening diseases. The binding AGEs their respective protein receptors for (RAGE) can initiate a cascade reactions, may alter physiological conditions. present work investigates potential 4-thiazolidinones as RAGE inhibitors. We performed an extensive computational study identify structural requirements needed act To achieve this goal, 4-thiazolidinone-based compounds available in PubChem, ZINC15, ChEMBL, and ChEBI databases were screened against (PDB: 4LP5), leading identification top five drug-like candidates with high affinity V‐domain catalytic region. Drug likeness, absorption, distribution, metabolism, excretion, toxicity (ADMET) top-scoring have studied discussed. Global molecular descriptors, chemical reactivity, hardness, softness, etc., estimated. Finally, dynamics (MD) simulations at 100 ns carried out check stability other properties. Overall, we believe that identified potentially attenuate RAGE–AGE interactions.

Language: Английский

Citations

1