ChemInform Abstract: Synthesis and Antimicrobial Evaluation of Some New 2‐(6‐Oxo‐5,6‐dihydro[1,3]thiazolo [3,2‐b]‐2‐aryloxymethyl‐1,2,4‐triazol‐5‐yl)‐N‐arylacetamides.

Lobo, Prajwal L.; Poojary, Boja; Kumsi, Manjunatha; Kumari, N. Suchetha

doi:10.1002/chin.201038139

Cited by 3 publications

(5 citation statements)

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“…Prompted by these findings and in continuation of our search for heterocyclic compounds which have antimicrobial activity, [36][37][38][39] that at 1711 and 1646 cm À 1 correspond to C=O stretching. The absorption band for C=C stretching is observed at 1608 cm À 1 .…”

Section: Introductionmentioning

confidence: 96%

“…Prompted by these findings and in continuation of our search for heterocyclic compounds which have antimicrobial activity, [36–39] a novel series of 2,3,5‐trisubstituted thiazolidinone derivatives i. e., 5‐aryl‐3‐(2,4‐difluorobenzyl)‐2‐(phenyl/(3‐fluorophenyl)imino)‐1,3‐thiazolidin‐4‐one, have been synthesized from 3‐(2,4‐difluorobenzyl)‐2‐((phenyl/(3‐fluorophenyl)imino)‐1,3‐thiazolidin‐4‐one. The present work summarizes synthesis, characterization and biological evaluation such as antimicrobial and antitubercular activity.…”

Section: Introductionmentioning

confidence: 99%

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2,3,5‐Trisubstituted Thiazolidinone Derivatives as Potential Antimicrobial and Antitubercular Agents and In Silico Studies

Nefisath,

Kumar,

Shashiprabha

et al. 2024

ChemistrySelect

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A series of novel 2,3,5‐trisubstituted thiazolidinone derivatives was designed and synthesized. Compounds were tested for their antimicrobial and antitubercular activities. Compounds 3‐(2,4‐difluorobenzyl)‐5‐[(5‐methylfuran‐2‐yl)methylidene]‐2‐(phenylimino)‐1,3‐thiazolidin‐4‐one (5 c) and 3‐(2,4‐difluorobenzyl)‐2‐((3‐fluorophenyl)imino)‐5‐((Z)‐4‐hydroxybenzylidene) thiazolidin‐4‐one (6 f) exhibited remarkable antimicrobial activity against Klebsiella pneumoniae and Escherichia coli respectively. All compounds except 3‐(2,4‐difluorobenzyl)‐5‐((3‐(4‐fluorophenyl)‐1‐phenyl‐1H‐pyrazol‐4‐yl)methylene)‐2‐(phenylimino)thiazolidin‐4‐one (5 a) and (6 f) exposed excellent antitubercular activity in comparison with the standard drugs against H37RV strain of Mycobacterium tuberculosis (ATCC No‐ 27294). In addition, molecular docking and dynamic simulations studies were performed with E. coli Mur B (EMB) (PDB ID: 2Q85), Aspergillus fumigatus sterol 14‐alpha demethylase (ASD) (PDB ID: 4UYM) and Mycobacterium tuberculosis pantothenate synthetase (MPS) (PDB ID: 3IVX) proteins against all compounds and the most potent compound (5 c) displayed higher binding proficiency. These compounds may serve as lead compounds for further optimization to achieve promising therapeutic properties.

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Section: Introductionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

2,3,5‐Trisubstituted Thiazolidinone Derivatives as Potential Antimicrobial and Antitubercular Agents and In Silico Studies

Nefisath,

Kumar,

Shashiprabha

et al. 2024

ChemistrySelect

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“…On the other hand, 5‐arylidene‐2,4‐thiazolidinediones, well‐known Michael acceptors, are known to exhibit a wide range of biological activities, including anti‐diabetic, [22] anti‐microbial, [23–26] anti‐fungal, [27] anti‐viral, [28] anti‐oxidant, [29] anti‐cancer, [30–32] hepatitis B virus inhibition, [33] obesity [34,35] and many more [36] . Recently, peptidyl 5‐arylidene‐2,4‐thiazolidinediones have been reported as 3CL Pro inhibitors [37,38] .…”

Section: Introductionmentioning

confidence: 99%

“…Besides, a carbamate derivative of peptidyl cinnamate (i, Figure 2) is another example of Michael acceptors acting as SARS-CoV-2 M pro (a cysteine protease of topical interest) inhibitors. [21] On the other hand, 5-arylidene-2,4-thiazolidinediones, wellknown Michael acceptors, are known to exhibit a wide range of including anti-diabetic, [22] antimicrobial, [23][24][25][26] anti-fungal, [27] anti-viral, [28] anti-oxidant, [29] anticancer, [30][31][32] hepatitis B virus inhibition, [33] obesity [34,35] and many more. [36] Recently, peptidyl 5-arylidene-2,4-thiazolidinediones have been reported as 3CL Pro inhibitors.…”

Section: Introductionmentioning

confidence: 99%

5‐Arylidene‐2,4‐thiazolidinediones as Cysteine Protease Inhibitors against Leishmania Donovani

Sharma,

Anjaneyulu Yakkala,

Beg

et al. 2023

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A series of 5‐arylidene‐2,4‐thiazolidinediones were synthesized using Knoevenagel condensation and evaluated for their anti‐leishmanial activity against L. donovani promastigotes and axenic amastigotes. Among the compounds tested, three were the most active, with IC50 values of 0.82–1.42 μM against L. donovani promastigotes and 0.69–1.19 μM against L. donovani amastigote. (Z)‐5‐(4‐(trifluoromethyl)benzylidene)thiazolidine‐2,4‐dione was the most prominent among all the tested compounds and demonstrated better anti‐leishmanial properties when compared to the standard drug miltefosine (1.26 μM against L. donovani promastigotes and 1.17 μM against L. donovani amastigotes). It was insignificantly toxic compared to the standard miltefosine in THP‐1 human monocytic cells. It was further evaluated for its in vitro cysteine protease (papain) inhibitory activity using Z‐RR‐AMC fluorogenic peptide substrate. It demonstrated promising inhibitory activity with the IC50 value of 3.42 μM. In silico docking studies also supported that the (Z)‐5‐(4‐(trifluoromethyl)benzylidene)thiazolidine‐2,4‐dione is bound to cysteine protease proteins′ catalytic active binding site. Anti‐leishmanial properties of this class of compounds have been evaluated for the first time, and (Z)‐5‐(4‐(trifluoromethyl)benzylidene)thiazolidine‐2,4‐dione emerged as a lead molecule from the library of compounds tested. This may serve as a template for further drug discovery in Leishmania.

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“…It should be noted that conducting the reaction utilising HCl as the acid and heating for a 7–8 hour period provided the highest yield of 3 at 94 % (Figure 3). [11,12] …”

Section: Introduction To Tzdmentioning

confidence: 99%

Thiazolidinediones: An In–Depth Study of Their Synthesis and Application to Medicinal Chemistry in the Treatment of Diabetes Mellitus

2021

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2,4‐Thiazolidinedione (TZD) is a privileged and highly utilised scaffold for the development of pharmaceutically active compounds. This sulfur‐containing heterocycle is a versatile pharmacophore that confers a diverse range of pharmacological activities. TZD has been shown to exhibit biological action towards a vast range of targets interesting to medicinal chemists. In this review, we attempt to provide insight into both the historical conventional and the use of novel methodologies to synthesise the TZD core framework. Further to this, synthetic procedures utilised to substitute the TZD molecule at the activated methylene C5 and N3 position are reviewed. Finally, research into developing clinical agents, which act as modulators of peroxisome proliferator‐activated receptors gamma (PPARγ), protein tyrosine phosphatase 1B (PTP1B) and aldose reductase 2 (ALR2), are discussed. These are the three most targeted receptors for the treatment of diabetes mellitus (DM).

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ChemInform Abstract: Synthesis and Antimicrobial Evaluation of Some New 2‐(6‐Oxo‐5,6‐dihydro[1,3]thiazolo [3,2‐b]‐2‐aryloxymethyl‐1,2,4‐triazol‐5‐yl)‐N‐arylacetamides.

Cited by 3 publications

References 1 publication

2,3,5‐Trisubstituted Thiazolidinone Derivatives as Potential Antimicrobial and Antitubercular Agents and In Silico Studies

2,3,5‐Trisubstituted Thiazolidinone Derivatives as Potential Antimicrobial and Antitubercular Agents and In Silico Studies

5‐Arylidene‐2,4‐thiazolidinediones as Cysteine Protease Inhibitors against Leishmania Donovani

Thiazolidinediones: An In–Depth Study of Their Synthesis and Application to Medicinal Chemistry in the Treatment of Diabetes Mellitus

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