Diversity-Oriented Synthesis of Thiazolidine-2-imines via Microwave-Assisted One-Pot, Telescopic Approach and Its Interaction with Biomacromolecules

Saikia, Ananya Anubhav; Rao, R. Nishanth; Maiti, B. R.; Balamurali, M. M.; Chanda, Kaushik

doi:10.1021/acscombsci.0c00083

Cited by 12 publications

(10 citation statements)

References 33 publications

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“…The interaction of the synthesized thiazol‐2( 3H )‐ones with acetylcholinesterase was examined at the active site. (Z)‐N‐((Z)‐5‐Benzylidene‐4‐tertbutyl‐3‐propylthiazolidin‐2‐ylidene)‐3‐methoxybenzenamine has been considered as the reference standard [20] . Our results imply that the binding energy varies in the following order: 3 g > 3 q > 3 s > 3 o > 3 i > 3 h > 3 t > 3 j > 3 p > 3 f > 3 l > 3 e > 3 a > 3 b > 3 k > 3 c > 3 m > 3 d > 3 n > 3 r .…”

Section: Resultsmentioning

confidence: 99%

Microwave‐Assisted Diversity‐Oriented Synthesis of Thiazol‐2(3H)‐ones and Its Interaction with Biomacromolecules

et al. 2022

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An expeditious catalyst-free heteroannulation has been accomplished to access functionalized thiazol-2(3H)ones by the reaction of isothiocyanates and 2-bromoketones in EtOH under controlled microwave irradiation heating. The synthetic strategy is simple, straightforward, and offers two points of structural diversity to expand the product versatility. Further, the biological relevance of the synthesized thiazol-2(3H)-ones has been examined for their possible use as putative acetylcholinesterase inhibitors through molecular docking analysis.

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Section: Resultsmentioning

confidence: 99%

Microwave‐Assisted Diversity‐Oriented Synthesis of Thiazol‐2(3H)‐ones and Its Interaction with Biomacromolecules

et al. 2022

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“…The standard drug molecule Isoniazid was used as a reference compound in all the screening studies. The binding site residues of Mycobacterium tuberculosis protein PrpR were obtained from the literature 32 …”

Section: Methodsmentioning

confidence: 99%

“…The binding site residues of Mycobacterium tuberculosis protein PrpR were obtained from the literature. 32…”

Section: Dataset Preparationmentioning

confidence: 99%

“…29,30 Recently, we have identified the chemical constituents of Tinospora Cordifolia as possible inhibitors of COVID-19 targets via computational approach. 31 As part of our ongoing programme for the identification bioactive compounds via computational approach, 32 we therefore, in the present investigation employed CADD for the investigation of a chemical library for potential inhibitors for TB. We have employed Glide docking and Prime-MM/generalized-born surface area (GBSA) analysis to improve the screening process.…”

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Exploration of potential inhibitors for tuberculosis via structure‐based drug design, molecular docking, and molecular dynamics simulation studies

2021

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Drug resistance in tuberculosis is major threat to human population. In the present investigation, we aimed to identify novel and potent benzimidazole molecules to overcome the resistance management. A series of 20 benzimidazole derivatives were examined for its activity as selective antitubercular agents. Initially, AutodockVina algorithm was performed to assess the efficacy of the molecules. The results are further enriched by redocking by means of Glide algorithm. The binding free energies of the compounds were then calculated by MM‐generalized‐born surface area method. Molecular docking studies elucidated that benzimidazole derivatives has revealed formation of hydrogen bond and strong binding affinity in the active site of Mycobacterium tuberculosis protein. Note that ARG308, GLY189, VAL312, LEU403, and LEU190 amino acid residues of Mycobacterium tuberculosis protein PrpR are involved in binding with ligands of benzimidazoles. Interestingly, the ligands exhibited same binding potential to the active site of protein complex PrpR in both the docking programs. In essence, the result portrays that benzimidazole derivatives such as 1p, 1q, and 1 t could be potent and selective antitubercular agents than the standard drug isoniazid. These compounds were then subjected to molecular dynamics simulation to validate the dynamics activity of the compounds against PrpR. Finally, the inhibitory behavior of compounds was predicted using a machine learning algorithm trained on a data collection of 15,000 compounds utilizing graph‐based signatures. Overall, the study concludes that designed benzimidazoles can be employed as antitubercular agents. Indeed, the results are helpful for the experimental biologists to develop safe and non‐toxic drugs against tuberculosis.

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“…Also, the Lipinski rule of five was analyzed to identify the drug interactions for safety and efficacy. As part of our on‐going programme for the identification of bioactive compounds via various computational approaches, 30 we have highlighted drug designing methods through various in‐silico studies including molecular docking and dynamic simulations, to identify the potential inhibitors of M. tuberculosis . In addition, ADMET prediction affords the permeability and bioavailability scores of molecules as necessary factor for drug designing process.…”

Section: Introductionmentioning

confidence: 99%

Identification of novel inhibitors for Prp protein of Mycobacterium tuberculosis by structure based drug design, and molecular dynamics simulations

et al. 2022

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In this study, we assess the effective inhibition of a series of thiazolidine derivatives (1a–1q) were adopting structure‐based drug design. Thiazolidine is a five‐membered ring structure with thioether and amino groups at positions 1 and 3. Although, thiazolidine may bind to a wide range of protein targets, it is a major heterocyclic core in medicinal chemistry. Different scoring utilities including AutoDock Vina, Glide, and MM/GBSA analysis were performed to commensurate the improvement of screening progress. The evaluated binding affinities were validated by molecular dynamics simulations over a period of 20 ns for the interactions between the Mycobacterium tuberculosis protein PrpR with three novel scaffolds (1b, 1j, and 1k). All the scaffolds exhibited distinct stable interactions with the significant residues like Arg169, Arg197, Tyr248, Arg308, and Gly311 respectively. Further, the inhibitory activities of scaffolds were predicted and evaluated by machine learning based algorithm to rank the above proposed compounds. This study reveals the potential of 1k and 1j as effective inhibitor candidates for the treatment of tuberculosis.

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Diversity-Oriented Synthesis of Thiazolidine-2-imines via Microwave-Assisted One-Pot, Telescopic Approach and Its Interaction with Biomacromolecules

Cited by 12 publications

References 33 publications

Microwave‐Assisted Diversity‐Oriented Synthesis of Thiazol‐2(3H)‐ones and Its Interaction with Biomacromolecules

Microwave‐Assisted Diversity‐Oriented Synthesis of Thiazol‐2(3H)‐ones and Its Interaction with Biomacromolecules

Exploration of potential inhibitors for tuberculosis via structure‐based drug design, molecular docking, and molecular dynamics simulation studies

Identification of novel inhibitors for Prp protein of Mycobacterium tuberculosis by structure based drug design, and molecular dynamics simulations

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