Synthesis and Antibacterial and Cytotoxic Activities of New <i>N</i>‐3 Substituted Thiazolidine‐2,4‐dione Derivatives Bearing the Pyrazole Moiety

Desai, N. C.; Satodiya, H. M.; Kotadiya, G. M.; Vaghani, H. V.

doi:10.1002/ardp.201300466

Cited by 17 publications

(11 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The same findings are suitable for 2,4-thiazolidinedione derivatives e N3 modification provides to 5e40 folds increasing of the antimicrobial activity (72) [200,201].…”

Section: Antimicrobial Agentssupporting

confidence: 57%

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

141

133

View full text Add to dashboard Cite

The presented review is an attempt to summarize a huge volume of data on 5-ene-4-thiazolidinones being a widely studied class of small molecules used in modern organic and medicinal chemistry. The manuscript covers approaches to the synthesis of 5-ene-4-thiazolidinone derivatives: modification of the C5 position of the basic core; synthesis of the target compounds in the one-pot or multistage reactions or transformation of other related heterocycles. The most prominent pharmacological profiles of 5-ene derivatives of different 4-thiazolidinone subtypes belonging to hit-, lead-compounds, drug-candidates and drugs as well as the most studied targets have been discussed. Currently target compounds (especially 5-en-rhodanines) are assigned as frequent hitters or pan-assay interference compounds (PAINS) within high-throughput screening campaigns. Nevertheless, the crucial impact of the presence/nature of C5 substituent (namely 5-ene) on the pharmacological effects of 5-ene-4-thiazolidinones was confirmed by the numerous listed findings from the original articles. The main directions for active 5-ene-4-thiazolidinones optimization have been shown: i) complication of the fragment in the C5 position; ii) introduction of the substituents in the N3 position (especially fragments with carboxylic group or its derivatives); iii) annealing in complex heterocyclic systems; iv) combination with other pharmacologically attractive fragments within hybrid pharmacophore approach. Moreover, the utilization of 5-ene-4-thiazolidinones in the synthesis of complex compounds with potent pharmacological application is described. The chemical transformations cover mainly the reactions which involve the exocyclic double bond in C5 position of the main core and correspond to the abovementioned direction of the 5-ene-4-thiazolidinone modification.

show abstract

“…The same findings are suitable for 2,4-thiazolidinedione derivatives e N3 modification provides to 5e40 folds increasing of the antimicrobial activity (72) [200,201].…”

Section: Antimicrobial Agentssupporting

confidence: 57%

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

141

133

View full text Add to dashboard Cite

show abstract

“…To explain quantitative structure-antibacterial activity relationships (Q-SAR) of the fifteen ( E )- N '-benzylidenebenzohydrazide analogues ( 3a-o) , physicochemical calculations were conducted using ChemBio3D Pro 12 molecular modeling (CambridgeSoft Corporation, Cambridge, MA 02140, USA) and Molinspiration Cheminformatics software (Molinspiration Cheminformatics, SK 90026 Slovensky Grob, SR). The physicochemical properties of molecules, such as, their lipophilicities and polar surface areas (PSAs) play important roles in determining biological responses, and are commonly used to study the structure-activity relationships of bioactive molecules in medicinal chemistry (Alam et al, 2013[ 6 ]; Desai et al, 2014[ 12 ]). These parameters are now well-accepted major experimental and theoretical tools for drug design and discovery.…”

Section: Resultsmentioning

confidence: 99%

Biological and quantitative-SAR evaluations, and docking studies of (E)-N'-benzylidenebenzohydrazide analogues as potential antibacterial agents

Alam

Jebin

Rahman

et al. 2016

EXCLI Journal; 15:Doc350; ISSN 1611-2156

View full text Add to dashboard Cite

“…Accordingly, logP and PSA are viewed as meaningful parameters in structureactivity relationship studies (Desai et al, 2014;Alam et al, 2013). To explain the quantitative structureactivity relationships (Q-SARs) of chalcones IIa-IIj and the corresponding 2,3-dibromo analogues IIIaIIIj, physicochemical calculations were performed using Molinspiration Cheminformatics software.…”

Section: Quantitative Structure-activity Relationship (Q-sar) Studymentioning

confidence: 99%

Synthesis, biological evaluation, quantitative-SAR and docking studies of novel chalcone derivatives as antibacterial and antioxidant agents

2015

View full text Add to dashboard Cite

In the present study, a series of chalcone derivatives including 17 new compounds were synthesised; their antibacterial activities against eleven bacteria, and their free radical-scavenging activities using DPPH were evaluated. All compounds showed significant antibacterial activities against both Grampositive and Gram-negative bacteria. In particular, compound IIIf strongly inhibited Staphylococcus aureus (JMC 2151) and Enterococcus faecalis (CARS 2011-012) with MIC values of 6.25 µg mL −1 and 12.5 µg mL −1 , respectively, which are comparable to that of the standard antibiotic, nalidixic acid. Compound IIIg also inhibited S. aureus with a MIC value similar to that of nalidixic acid (6.25 µg mL −1 ). Furthermore, like nalidixic acid (MIC value of 25 µg mL −1 ), compounds IIIa, IIIc and IIId inhibited Listeria monocytogenes (ATCC 43256) with MIC values of 25 µg mL −1 , 12.5 µg mL −1 and 25 µg mL −1 , respectively. Quantitative structure-activity relationship (Q-SAR) studies using physicochemical calculations indicated that the antibacterial activities of chalcone derivatives correlated well with predicted physicochemical parameters (logP and PSA). Docking simulation by positioning the most active compound IIIf in the active site of the penicillin-binding protein (PBP-1b) of S. aureus was performed to explore the feasible binding mode. Furthermore, most of the compounds synthesised exhibited significant DPPH radical-scavenging activity, although compounds IIc and IIIc exhibited the greatest antioxidant activity with IC50 values of 1.68 µM and 1.44 µM, respectively, comparable to that of the standard antioxidant, ascorbic acid (1.03 µM).

show abstract

Synthesis and Antibacterial and Cytotoxic Activities of New N‐3 Substituted Thiazolidine‐2,4‐dione Derivatives Bearing the Pyrazole Moiety

Cited by 17 publications

References 41 publications

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Biological and quantitative-SAR evaluations, and docking studies of (E)-N'-benzylidenebenzohydrazide analogues as potential antibacterial agents

Synthesis, biological evaluation, quantitative-SAR and docking studies of novel chalcone derivatives as antibacterial and antioxidant agents

Contact Info

Product

Resources

About