Facile synthesis of 1,3-thiazolidin-4-ones as antitubercular agents

Subhedar, Dnyaneshwar D.; Shaikh, Mubarak H.; Arkile, Manisha; Yeware, Amar; Sarkar, Dhiman; Shingate, Bapurao B.

doi:10.1016/j.bmcl.2016.02.056

Cited by 59 publications

(28 citation statements)

References 52 publications

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“…This is agreeing with a previous result. 20) However, the pyrano [2,3d] thiazole derivatives (6a-d) were obtained by the reaction of the 5-arylmethylidene-thiazolidin-4-one derivatives (5a-d) with malononitrile in boiling ethanol in presence of catalytic amount of triethylamine (Chart 2). The structures of compounds (6a-d) were excluded on the basis of elemental analyses and spectral data (cf.…”

Section: Resultsmentioning

confidence: 99%

“…[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%

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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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Section: Resultsmentioning

confidence: 99%

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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“…Subhedar et al [81] observed one-pot, multicomponent reaction (MCR) using [Et 3 NH][HSO 4 ] as a catalyst, and the products were found in excellent yields with [80] a high purity, whereas lower yields were obtained in the absence of the catalyst. An environmentally and highly efficient protocol for 1,3-thiazolidin-4-ones was prepared from cyclocondensation of aniline, aromatic aldehyde and thioglycolic acid with [Et 3 NH][HSO 4 ] (Scheme 23).…”

Section: Ionic Liquid-assisted Synthesismentioning

confidence: 99%

“…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. 3).…”

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)

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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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“…Good yields of the thiazolidins were synthesized by a cyclocondensation reaction that was catalyzed by [Et 3 NH][HSO4] in good yield. All of the new compounds were screened against the M. tuberculosis ATCC25177 strain, and Compound 65 (Figure ) exhibited the best activity of the new compounds, with an IC 50 value of 2.20 μg/ml (Subhedar et al, ).…”

Section: Five‐membered Ring Compoundsmentioning

confidence: 99%

Opportunities and challenges of using five‐membered ring compounds as promising antitubercular agents

Wang

et al. 2020

Drug Development Research

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Tuberculosis (TB), a chronic infectious disease, is one of the greatest risks to human beings and 10 million people were diagnosed with TB and 1.6 million died from this disease in 2017. In addition, with the emergence of multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB), the TB situation has become even worse, which has aggravated the mortality and spread of this disease.To overcome this problem, research into novel antituberculosis agents with enhanced activities against MDR-TB, reduced toxicity, and shortened duration of therapy is of great importance. Fortunately, many novel potential anti-TB drug candidates with five-membered rings, which are most likely to be effective against sensitive and resistant strains, have recently entered clinical trials. Different five-membered rings such as furans, pyranoses, thiazoles, pyrazolines, imidazoles, oxazolidinone, thiazolidins, isoxazoles, triazoles, oxadiazoles, thiadiazoles, and tetrazoles have been designed, prepared, and evaluated for their antimycobacterial activity against Mycobacterium tuberculosis. In this article, we highlight the recent advances made in the discovery of novel five-membered ring compounds and focus on their antitubercular activities, toxicity, structure-activity relationships, and mechanisms of action. K E Y W O R D Santi-TB drug, antitubercular activities, five-membered ring, MDR-TB, tuberculosis

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Facile synthesis of 1,3-thiazolidin-4-ones as antitubercular agents

Cited by 59 publications

References 52 publications

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

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

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

Opportunities and challenges of using five‐membered ring compounds as promising antitubercular agents

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