Design, Synthesis of Biologically Active Heterocycles Containing Indol- Thiazolyl- Thiazolidinone Derivatives

Walmik, Prabhaker; Naraboli, Basavaraj S; Swathi, B; Ghanti, S. Kiran

doi:10.22159/ajpcr.2018.v11i3.22199

Cited by 7 publications

(4 citation statements)

References 27 publications

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“…The indole–thiazolidinone–thiazole hybrids 42 (MIC: 62.5–500 μg/ml) were active against bacteria E. coli , S. aureus , K. pneumoniae , and P. aeruginosa , and fungi A. oryzae , A. niger , A. flavus , and A. terreus . [ 97 ] The SAR revealed that removal of the thiazolidinone moiety led to a great loss of activity. [ 98 ] In particular, the antibacterial and antifungal activity of hybrid 42b (MIC: 62.5–125 μg/ml) was 2–8‐fold more potent than that of gentamycin (MIC: 125–250 μg/ml) and fluconazole (MIC: 62.5–250 μg/ml) against most of the tested organisms.…”

Section: Indole/isatin–azole Hybridsmentioning

confidence: 99%

Indole/isatin‐containing hybrids as potential antibacterial agents

Song

Bian

et al. 2020

Archiv der Pharmazie

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The emergence and worldwide spread of drug-resistant bacteria have already posed a serious threat to human life, creating the urgent need to develop potent and novel antibacterial drug candidates with high efficacy. Indole and isatin (indole-2,3-dione) present a wide structural and mechanistic diversity, so their derivatives possess various pharmacological properties and occupy a salient place in the development of new drugs. Indole/isatin-containing hybrids, which demonstrate a promising activity against a panel of clinically important Gram-positive and Gram-negative bacteria, are privileged scaffolds for the discovery of novel antibacterial candidates. This review, covering articles published between January 2015 and May 2020, focuses on the development and structure-activity relationship (SAR) of indole/isatincontaining hybrids with potential application for fighting bacterial infections, to facilitate further rational design of novel drug candidates.

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Section: Indole/isatin–azole Hybridsmentioning

confidence: 99%

Indole/isatin‐containing hybrids as potential antibacterial agents

Song

Bian

et al. 2020

Archiv der Pharmazie

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“…Results of their antibacterial and antifungal activities [28] of synthesized compounds (12a-h) are shown in Tables 4 and 5, respectively. Most of the compounds exhibited potent antibacterial as well as antifungal activity against all the microbes tested as compared to the standard drugs used (i.e., ciprofloxacin and fluconazole for bacterial and fungal strains, respectively).…”

Section: Pharmacological Activitymentioning

confidence: 99%

Design, Synthesis, Molecular Docking, and Evaluation of Chromone Based Tetrazole Derivatives

Chopra¹,

Singh²,

Vk³

et al. 2019

Asian J Pharm Clin Res

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Objectives: The objective of this research work was to design, synthesize, study the molecular docking, and evaluate the antimicrobial activity of some novel substituted 2-(Phenylamino)-3-(1H-tetrazol-5-yl)-4H-chromen-4-one derivatives (12a-h). Methods: In the present work, 3-Formylchromones were transformed into pharmacologically active substituted 2-(Phenylamino)-3-(1H-tetrazol-5- yl)-4H-chromen-4-one derivatives (12a-h) through a multistep reaction. Initially, synthesis of the substituted 4-Oxo-2-(phenylamino)-4H-chromone-3- carbaldehydes (9a-h) was carried out using substituted acetophenones (6a-h) as starting material and by employing an earlier reported method (1,3-dipolar cycloaddition reaction). Then, these synthesized compounds were converted into respective oximes (10a-h).The obtained oximes (10a-h) were further converted into nitriles (11a-h) which were finally subjected to concerted cycloaddition through stepwise addition of neutral or anionic azide species to furnish final substituted 2-(Phenylamino)-3-(1H-tetrazol-5-yl)-4H-chromen-4-one derivatives (12a-h). All the newly synthesized compounds (12a-h) and a reference compound (ciprofloxacin) were docked into the active site of TyrRS (PDB: 1JIK) by means of the BioPredicta module of VLife MDS. The synthesized compounds (12a-h) were also evaluated in vitro for their antibacterial (against Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa, and Escherichia coli bacterial stains) and antifungal activities (against Aspergillus niger and Candida albicans fungal strains) using Zone of Inhibition method. Results: The formation of substituted 2-(Phenylamino)-3-(1H-tetrazol-5-yl)-4H-chromen-4-one derivatives (12a-h) was confirmed through their spectral analysis, that is, 1H-NMR, 13C-NMR, and Mass spectroscopy. During docking study, the recorded molecular binding interactions revealed that all the newly synthesized compounds (12a-h) interacted well with binding site of the enzyme. The synthesized compounds were also evaluated in vitro for their antibacterial (against S. aureus, B. subtilis, P. aeruginosa, and E. coli bacterial stains) and antifungal activities (against A. niger and C. albicans fungal strains). All the synthesized compounds exhibited moderate-to-potent antimicrobial activities. Conclusions: All the synthesized compounds exhibited moderate-to-potent antimicrobial activity.

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“…PPARγ helps in glucose and lipid uptake, kindles glucose oxidation, decreases free fatty acid level, and improves insulin resistance. They are highly present in adipose tissues that play a significant role on insulin resistance, cell differentiation, and energy metabolism [8][9][10]. All the PPARs have similar structures and mechanism of action.…”

Section: Introductionmentioning

confidence: 99%

In SILICO DESIGN OF QUINOXALINE BEARING THIAZOLIDINONE DERIVATIVES AS PPARγ AGONIST IN DIABETES MELLITUS

Poornima

Anjana

2021

Asian J Pharm Clin Res

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Objective: Diabetes mellitus is a set of metabolic disease in which there is increased blood sugar level over a long period. The objective of the study is in silico design of quinoxaline bearing thiazolidinone derivatives as peroxisome proliferator-activated receptor gamma (PPARγagonist in diabetes mellitus. Methods: In silico design of proposed derivatives was conducted by ACD Lab ChemSketch 12.0 and derivatives obeying Lipinski’s rule of five were selected for docking studies. Docking was carried out using AutoDock Vina software. Results: Molinspiration results revealed that the designed derivatives had physical and chemical properties meant for an orally available drug. Based on the docking results derivatives, QNT1 and QNT2 exhibited high docking score which indicates that these derivatives possess high-affinity and high polar interaction toward protein 1PRG (ligand-binding domain of human peroxisome proliferator-activated receptor gamma). Conclusion: The designed quinoxaline bearing thiazolidinone derivatives were found to possess good binding affinity and good interaction in the binding pocket of target 1PRG, so these derivatives are expected to exhibit good antidiabetic property with minimal side effects.

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Design, Synthesis of Biologically Active Heterocycles Containing Indol- Thiazolyl- Thiazolidinone Derivatives

Cited by 7 publications

References 27 publications

Indole/isatin‐containing hybrids as potential antibacterial agents

Indole/isatin‐containing hybrids as potential antibacterial agents

Design, Synthesis, Molecular Docking, and Evaluation of Chromone Based Tetrazole Derivatives

In SILICO DESIGN OF QUINOXALINE BEARING THIAZOLIDINONE DERIVATIVES AS PPARγ AGONIST IN DIABETES MELLITUS

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