Thiazolidin-4-ones from 4-(methylthio)benzaldehyde and 4-(methylsulfonyl)benzaldehyde: Synthesis, antiglioma activity and cytotoxicity

Silva, Daniel Schuch da; Silva, Cesar Emiliano Hoffmann da; Soares, Mayara Sandrielly Pereira; Azambuja, Juliana H.; Carvalho, Taíse Rosa de; Zimmer, Geórgia C.; Frizzo, Clarissa P.; Braganhol, Elizandra; Spanevello, Rosélia Maria; Cúnico, Wilson

doi:10.1016/j.ejmech.2016.08.057

Cited by 24 publications

(13 citation statements)

References 24 publications

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“…The anti-glioma activity and cytotoxicity of the thiazolidin-4-ones were evaluated by Da Silva and coworkers [62]. In this procedure, primary amines, aldehyde and mercaptoacetic acid were reacted via one-pot MCR in the presence of BF 3 and p-toluenesulfonic acid (PTSA) and formed derivatives of thiazolidin-4-one (Scheme 5).…”

Section: Figmentioning

confidence: 99%

“…Nanjan et al [57] reviewed the antidiabetic activity of thiazolidinone. But there is no detailed review of the synthesis and biological activity of 4 Comparative study of various synthetic protocols [58][59][60][61][62][63][64][65][66][67][68][69] Fig. 5 Comparative study of various synthetic protocols [77][78][79][80][81][82][83][84][85][86] Topics in Current Chemistry (2020) 378:34 1 3 34 Page 8 of 90 hoping to inspire new and even more creative approaches for researchers ( Fig.…”

Section: Introductionmentioning

confidence: 99%

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

Sahiba¹,

Sethiya²,

Soni³

et al. 2020

Top Curr Chem (Z)

101

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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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Section: Figmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

Sahiba¹,

Sethiya²,

Soni³

et al. 2020

Top Curr Chem (Z)

101

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“…Thiazolidinone belongs to this class and is a versatile scaffold to the development of new bioactive compounds. Numerous studies describe a wide range of pharmacological properties of thiazolidinones: anti-HIV 12 , antitumor 13 , 14 , anti-inflammatory 15 , antimicrobial 16 , antihyperglycemic 17 , and acetyl/butyrylcholinesterase inhibition 5 . Thiazinanones (six-membered heterocycle) also show important biological activity such as anticancer 18 , antimalarial 19 , antihypertensive 20 , antibacterial 21 , and antihyperglycemic 17 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of thiazolidin-4-ones and thiazinan-4-ones from 1-(2-aminoethyl)pyrrolidine as acetylcholinesterase inhibitors

Neves

Berwaldt

Avila

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

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The present study describes the synthesis of a novel series of thiazolidin-4-one and thiazinan-4-one using 1-(2-aminoethyl)pyrrolidine as amine precursor. All compounds were synthesised by one-pot three component cyclocondensation reaction from the amine, a substituted benzaldehyde and a mercaptocarboxylic acid. The compounds were obtained in moderate to good yields and were identified and characterised by 1 H, 13 C, 2 D NMR and GC/MS techniques. The compounds also were screened for their in vitro acetylcholinesterase (AChE) activity in hippocampus and cerebral cortex on Wistar rats. The six most potent compounds have been investigated for their cytotoxicity by cell viability assay of astrocyte primary culture, an important cell of central nervous system. We highlighted two compounds (6a and 6k) that had the lowest IC 50 in hippocampus (5.20 and 4.46 mM) and cerebral cortex (7.40 and 6.83 mM). These preliminary and important results could be considered a starting point for the development of new AChE inhibitory agents.

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“…[8][9][10][11][12][13] Furthermore, some of them were reported to possess antiviral, 14) antidiabetic, 15,16) antiinflammatory 17,18) and antimalarial 19) activities. Moreover, various substituted rhodanines were found to be anti-tubercular, 20,21) antiproliferative agent against human colon cancer, 22) anti-human immunodeficiency virus (HIV), [23][24][25][26][27] cyclooxygenase (COX-2) inhibitors, 28) potent PTP1B inhibitors, 29) antiglioma and cytotoxicity. 30) Additionally, rhodanine-based molecules have been popular as small molecule inhibitors of numerous targets such as Hepatitis C virus NS3 protease, 31) β-lactamase, 32) uridine diphospho-N-acetylmuramate/L-alanine ligase, 33) cathepsin D 34) and c-Jun N-terminal kinase (JNK)stimulating phosphatase-1 (JSP-1), 35) while some of rhodanine derivatives are used for the analysis of certain noble metal ions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, <i>in-Vitro</i> Cytotoxicity and Antimicrobial Evaluations of Some Novel Thiazole Based Heterocycles

El-Mawgoud

2019

Chem. Pharm. Bull.

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Condensation of rhodanine (1) with pyrazol-3(2H)-one derivatives (2a-f) gave 5-substituted-2-thioxo-1,3thiazolidin-4-one derivatives (3a-f). Reaction of compound (1) with 2-arylmethylidene-malononitrile (4a-d) yielded the unexpected derivatives (5a-d). The latter compounds were subjected to cyclization reactions with malononitrile under different basic conditions, hydroxylamine hydrochloride and/or thiourea to furnish the fused thiazole derivatives (6a-d) and (8-10a-d). Coupling of (1) with diazotized aromatic amines (11a-c) in pyridine afforded the arylhydrazones (12a-c). Fusion of latter compounds with malononitrile afforded the thiazolopyridazine derivatives (13a-c). The structures of the newly synthesized compounds were elucidated via spectral data and elemental analyses. The in-vitro cytotoxic activity of compounds (3a-f) against the cell line MCF-7 was evaluated. Also, the synthesized products were investigated for their antibacterial and antifungal activities against six standard organisms including the G bacteria, Staphylococcus aureus and Bacillus subtilis, G bacteria, Escherichia coli and Proteus vulgaris in addition to fungi, Candida albicans and Aspergillus flavus.

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Thiazolidin-4-ones from 4-(methylthio)benzaldehyde and 4-(methylsulfonyl)benzaldehyde: Synthesis, antiglioma activity and cytotoxicity

Cited by 24 publications

References 24 publications

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

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

Synthesis of thiazolidin-4-ones and thiazinan-4-ones from 1-(2-aminoethyl)pyrrolidine as acetylcholinesterase inhibitors

Synthesis, <i>in-Vitro</i> Cytotoxicity and Antimicrobial Evaluations of Some Novel Thiazole Based Heterocycles

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