<b>Synthesis and DNA‐binding study of imidazole linked thiazolidinone derivatives</b>

War, Javeed Ahmad; Srivastava, Santosh K.; Srivastava, S. K.

doi:10.1002/bio.3156

Cited by 13 publications

(6 citation statements)

References 63 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…One of the discussed modes of action of thiazolidinone based compound is the DNA-binding process. In this study 2-imino derivatives 90 were designed and the most potent molecule bound at the DNA minor groove involving Van der Waals, H-bonding and hydrophobic interactions [217] (Scheme 43).…”

Section: Antiparasitic Agentsmentioning

confidence: 99%

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

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

145

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

Section: Antiparasitic Agentsmentioning

confidence: 99%

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

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

145

133

View full text Add to dashboard Cite

show abstract

“…Among the 5-ene-2-amino(imino)-4-thiazolidinones, active anticancer agents which are capable of inhibiting the growth of cancer cells were identified both in screening campaigns and small-scale studies 15–21 . Many ligands exhibiting high affinity to the known anticancer targets were also described, including integrin αVβ3 antagonists 22 , inhibitors of CDK1/cyclin B 23,24 , PPAR antagonists 25 , estrogen-related receptor-α modulators 26 , SHP-2 inhibitors 27 , PTP1B inhibitors 28 , DNA-binding agents (which bind with the DNA minor groove involving van der Waals, H-bonding, and hydrophobic interactions) 29 , and so on. Very few attempts have been made to outline the main molecular modes of action of 5-ene-2-amino(imino)-4-thiazolidinones 1,30 .…”

Section: Introductionmentioning

confidence: 99%

Anticancer properties of 5Z-(4-fluorobenzylidene)-2-(4-hydroxyphenylamino)-thiazol-4-one

Szychowski

Kaminskyy

Leja

et al. 2019

Sci Rep

View full text Add to dashboard Cite

4-thiazolidinones, which are privileged structures in medicinal chemistry, comprise the well-known class of heterocycles and are a source of new drug-like compounds. Undoubtedly, the 5-bulky-substituted-2,4-thiazolidinediones - a class of antihyperglycemic glitazones, which are peroxisome proliferator-activated receptor gamma (PPARγ) agonists, are the most described group among them. As there are various chemically distinct 4-thiazolidinones, different subtypes have been selected for studies; however, their main pharmacological profiles are similar. The aim of this study was to evaluate the anticancer activity of 5 Z -(4-fluorobenzylidene)-2-(4-hydroxyphenylamino)-thiazol-4-one (Les-236) in four human cancer cell lines, A549, SCC-15, SH-SY5Y, and CACO-2, and investigate its impact on the production of reactive oxygen species (ROS) and the apoptotic process as well as cytotoxicity and metabolism in these cell lines. The cell lines were exposed to increasing concentrations (1 nM to 100 µM) of the studied compound for 6, 24, and 48 h, and later, ROS production, cell viability, caspase-3 activity, and cell metabolism were examined. The obtained results showed that the studied compound decreased the production of ROS, increased the release of lactate dehydrogenase, and decreased cell metabolism/proliferation in all the five cell lines at micromolar concentrations. Interestingly, over a wide range of concentrations (from 1 nM to 100 µM), Les-236 was able to increase the activity of caspase-3 in BJ (after 6 h of exposure), A549, CACO-2, and SCC-15 (after 48 h of exposure) cell lines which could be an effect of the activation of PPARγ-dependent pathways.

show abstract

“…Imidazole polyamides constitute a highly active structural group which shows anti-cancerous properties by binding at DNA minor groove [13,14]. Combining multiple pharmacophoric units into a single molecule has been a successful method to design new drug candidates in structure based drug design [15].…”

Section: Introductionmentioning

confidence: 99%