Novel thiazolidines: Synthesis, antiproliferative properties and 2D-QSAR studies

Singh, Ravi P.; Aziz, Marian N.; Gout, Delphine; Fayad, Walid; El-Manawaty, May A.; Lovely, Carl J.

doi:10.1016/j.bmc.2019.115047

Cited by 18 publications

(9 citation statements)

References 27 publications

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“…Combination of a methoxy and a nitro group in compound 5k did not cause a significant effect on the corresponding potency (1.38 μM), which is still close to a single methoxy substituted phenyl group (compound 5i with IC 50 = 1.75 μM) and nitro group (compound 5e with IC 50 = 1.15 μM). The activity of the current library of thiazolidines is not only consistent with our previously published series, but it shows a good improvement in terms of IC 50 values [ 13 ]. IC 50′ s of the previously synthesized thiazolidines ranged from 7.4–28.7 µM ( Scheme 1 ), while the new derivatives ranged from 0.27–16.32 µM ( Table 1 ).…”

Section: Resultssupporting

confidence: 86%

“…Analysis of compound 5f via X-ray single crystal shows the constitution is as expected and that the geometry of the two exocyclic double bonds is exhibiting the same geometry of the previous reported thiazolidines, Z , Z ’-configurations [ 13 ]. Colorless needle crystals of compound 5f crystallized in a monoclinic space group P2 1 /c with four molecules per unit cell.…”

Section: Resultssupporting

confidence: 71%

“…Breast cancer is among the most feared of women’s diseases due to the fact there are multiple genotypes and phenotypes and that it is a metastatic and heterogenous solid tumor [ 6 ]. Therefore, there are a number of published studies focused on developing novel lead/hit compounds containing thiazolidines targeting cancers [ 7 , 8 , 9 , 10 , 11 , 12 , 13 ]. Figure 1 shows three different compounds described in recently published studies, in which novel thiazolidine analogues are reported as anti-proliferative agents targeting breast cancer [ 14 , 15 , 16 ].…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, we have focused on developing this interesting one-pot chemistry further to access bio-active thiazolidine-based structures easily [ 36 ]. In 2019, our group published the synthesis of a novel group of thiazolidines using this procedure, some of which were prone to oxidation at C4 upon extended exposure to the ambient atmosphere producing thiazolidinones ( Scheme 1 ) [ 13 ]. Most of the reported compounds showed good anti-tumor activity against colon and breast cancers (in vitro study using HCT116 and MCF7 cell lines), which inspired us to design new analogs belonging to thiazolidines system only.…”

Section: Introductionmentioning

confidence: 99%

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One-Pot Synthesis of Novel 2-Imino-5-Arylidine-Thiazolidine Analogues and Evaluation of Their Anti-Proliferative Activity against MCF7 Breast Cancer Cell Line

et al. 2022

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An efficient surface-mediated synthetic method to facilitate access to a novel class of thiazolidines is described. The rationale behind the design of the targeted thiazolidines was to prepare stable thiazolidine analogues and evaluate their anti-proliferative activity against a breast cancer cell line (MCF7). Most of the synthesized analogues exhibited increased potency ranging from 2–15-fold higher compared to the standard reference, cisplatin. The most active thiazolidines contain a halogenated or electron withdrawing group attached to the N-phenyl ring of exocyclic 2-imino group. However, combination of the two substituents did not enhance the activity. The anti-proliferative activity was measured in terms of IC50 values using an MTT assay.

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Section: Resultssupporting

confidence: 86%

Section: Resultssupporting

confidence: 71%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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One-Pot Synthesis of Novel 2-Imino-5-Arylidine-Thiazolidine Analogues and Evaluation of Their Anti-Proliferative Activity against MCF7 Breast Cancer Cell Line

et al. 2022

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“…Abdel Hafez and coworkers [103] developed a series of 2-(2-(1-(3,4-dimethoxyphenyl)ethylidine)hydrazono)-substituted thiazolidinone derivatives and tested them for antimicrobial activity against fungal strains (A. niger and A. flavus) and yeast strains (S. cerevisiae, C. albicans). Thiosemicarbazone derivatives (57a and 57b) were refluxed with appropriate α-halo carbonyl compounds such as chloroacetone and ethyl 2-bromopropanoate using anhydrous sodium acetate in ethanol to produce corresponding thiazolidine analogs 58 and 59 (Scheme 50).…”

Section: Antimicrobial Activitymentioning

confidence: 99%

Saturated Five-Membered Thiazolidines and Their Derivatives: From Synthesis to Biological Applications

Sahiba¹,

Sethiya²,

Soni³

et al. 2020

Top Curr Chem (Z)

100

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In past decades, interdisciplinary research has been of great interest for scholars. Thiazolidine motifs behave as a bridge between organic synthesis and medicinal chemistry and compel researchers to explore new drug candidates. Thiazolidine motifs are very intriguing heterocyclic five-membered moieties present in diverse natural and bioactive compounds having sulfur at the first position and nitrogen at the third position. The presence of sulfur enhances their pharmacological properties, and, therefore, they are used as vehicles in the synthesis of valuable organic combinations. They show varied biological properties viz. anticancer, anticonvulsant, antimicrobial, anti-inflammatory, neuroprotective, antioxidant activity and so on. This diversity in the biological response makes it a highly prized moiety. Based on literature studies, various synthetic approaches like multicomponent reaction, click reaction, nano-catalysis and green chemistry have been employed to improve their selectivity, purity, product yield and pharmacokinetic activity. In this review article, we have summarized systematic approaches for the synthesis of thiazolidine and its derivatives, along with their pharmacological activity, including advantages of green synthesis, atom economy, cleaner reaction profile and catalyst recovery which will help scientists to probe and stimulate the study of these scaffolds.

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Potential Fluorinated Anti‐MRSA Thiazolidinone Derivatives with Antibacterial, Antitubercular Activity and Molecular Docking Studies

Poojary

Kumar

Premalatha³

et al. 2022

Chemistry & Biodiversity

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MRSA infection is one of the alarming diseases in the current scenario. Identifying newer molecules to treat MRSA infection is of urgent need. In the present study, we have designed fluorinated thiazolidinone derivatives with various aryl/heteroaryl units at 5 th position of the thiazolidinone core as promising anti-MRSA agents. All the compounds were screened for antibacterial activity against four bacterial strains. Among the tested compounds, the halogenated compounds with simple arylidene ring, (5Z 4f) and (5Z)-5-[(3,5-difluorophenyl)methylidene]-2-[(1,3-thiazol-2-yl)amino]-1,3thiazol-4(5H)-one (4g) showed excellent activity with MIC 3.125 -6.25 μg/mL against S. aureus and P. aeruginosa organism. Furthermore, these potent compounds were screened against MRSA strains, ESKAPE panel organism, and H37Rv mycobacterium strain. Compounds 4c (MIC 0.39 μg/mL), and 4f (MIC 0.39 and 0.79 μg/mL) displayed promising activity against MRSA strains (ATCC and clinical isolates, respectively). The most potent compounds, 4c and 4f eradicated the growth of bacterial colonies in a time-kill assay indicated that these are bactericidal in nature. The preliminary toxicity study of the potent molecules revealed that these compounds are non-hemolytic in nature as they did not induce lysis in human RBCs. In addition, the molecular docking and dynamics studies of compounds 4b, 4c, 4f and 4g were carried out on MurB protein of S. aureus (PDB code: 1HSK). Docking results demonstrated remarkable hydrogen bonding interaction with key amino acids ARG310, ASN83, GLY79 and π-π interactions with TYR149 which confirm the mode of action of the molecules.

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Novel thiazolidines: Synthesis, antiproliferative properties and 2D-QSAR studies

Cited by 18 publications

References 27 publications

One-Pot Synthesis of Novel 2-Imino-5-Arylidine-Thiazolidine Analogues and Evaluation of Their Anti-Proliferative Activity against MCF7 Breast Cancer Cell Line

One-Pot Synthesis of Novel 2-Imino-5-Arylidine-Thiazolidine Analogues and Evaluation of Their Anti-Proliferative Activity against MCF7 Breast Cancer Cell Line

Saturated Five-Membered Thiazolidines and Their Derivatives: From Synthesis to Biological Applications

Potential Fluorinated Anti‐MRSA Thiazolidinone Derivatives with Antibacterial, Antitubercular Activity and Molecular Docking Studies

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