The bioisosteric modification of pyrazinamide derivatives led to potent antitubercular agents: Synthesis via click approach and molecular docking of pyrazine-1,2,3-triazoles

Reddyrajula, Rajkumar; Dalimba, Udayakumar

doi:10.1016/j.bmcl.2019.126846

Cited by 45 publications

(30 citation statements)

References 36 publications

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“…We synthesized compound 3 by modifying a literature‐reported procedure. [36] To a suspension of pyrazinoic acid 1 (1 equiv.) in N , N ‐dimethylformamide (DMF; 10 ml), K 2 CO 3 (1.4 equiv.)…”

Section: Methodsmentioning

confidence: 99%

New Pyrazine Conjugates: Synthesis, Computational Studies, and Antiviral Properties against SARS‐CoV‐2

et al. 2021

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Currently, limited therapeutic options are available for severe acute respiratory syndrome coronavirus‐2 (SARS‐CoV‐2). We have developed a set of pyrazine‐based small molecules. A series of pyrazine conjugates was synthesized by microwave‐assisted click chemistry and benzotriazole chemistry. All the synthesized conjugates were screened against the SAR‐CoV‐2 virus and their cytotoxicity was determined. Computational studies were carried out to validate the biological data. Some of the pyrazine‐triazole conjugates ( 5 d – g ) and ( S )‐N‐(1‐(benzo[d]thiazol‐2‐yl)‐2‐phenylethyl)pyrazine‐2‐carboxamide 12 i show significant potency against SARS‐CoV‐2 among the synthesized conjugates. The selectivity index (SI) of potent conjugates indicates significant efficacy compared to the reference drug (Favipiravir).

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Section: Methodsmentioning

confidence: 99%

New Pyrazine Conjugates: Synthesis, Computational Studies, and Antiviral Properties against SARS‐CoV‐2

et al. 2021

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“…Few nicotine and nicotinamide based anti-TB agents are also reported in literature. [27][28][29][30] Recently Reddyrajula et. al., reported several 1,2,3-triazole based pyrazine, pyrazinamide and nicotinamide analogues as good anti-TB agents and most of the compounds exhibited promising activity with MIC 1.56 mg mL À1 to 25.0 mg mL À1 .…”

Section: Introductionmentioning

confidence: 99%

“…al., reported several 1,2,3-triazole based pyrazine, pyrazinamide and nicotinamide analogues as good anti-TB agents and most of the compounds exhibited promising activity with MIC 1.56 mg mL À1 to 25.0 mg mL À1 . 30 Compound K is one of the most active nicotinamide analogue with MTB MIC 1.56 mg mL À1 (Fig. 3).…”

Section: Introductionmentioning

confidence: 99%

Seeking potent anti-tubercular agents: design and synthesis of substituted-N-(6-(4-(pyrazine-2-carbonyl)piperazine/homopiperazine-1-yl)pyridin-3-yl)benzamide derivatives as anti-tubercular agents

et al. 2020

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“…It has been introduced to evaluate the constituents and action mechanisms of TCM in view of its systematic and holistic coincides ( Li et al, 2011 ; Li and Zhang, 2013 ; Cai et al, 2018a ). Molecular docking is a technology of drug design and screening based on computer data simulation through the interaction and affinity between receptor macromolecules and drug micromolecules ( Chen et al, 2014 ; Lionta et al, 2014 ; Saikia and Bordoloi, 2019 ; Reddyrajula and Dalimba, 2020 ). At present, their combined use has been successfully applied in the research of Traditional Chinese medicine and their compound preparation ( Liang et al, 2019 ; Wang et al, 2019 ).…”

Section: Introductionmentioning

confidence: 99%

Qing-Yi Decoction in the Treatment of Acute Pancreatitis: An Integrated Approach Based on Chemical Profile, Network Pharmacology, Molecular Docking and Experimental Evaluation

et al. 2021

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Background: Qing-Yi Decoction (QYD) is a classic precompounded prescription with satisfactory clinical efficacy on acute pancreatitis (AP). However, the chemical profile and overall molecular mechanism of QYD in treating AP have not been clarified.Methods: In the present study, a rapid, simple, sensitive and reliable ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UHPLC-QTOF-MS)-based chemical profile was first established. An integration strategy of network pharmacology analysis and molecular docking based identified ingredients was further performed to screen out the potential targets and pathways involved in the treatment of QYD on AP. Finally, SD rats with acute pancreatitis were constructed to verify the predicted results through a western blot experiment.Results: A total of 110 compounds, including flavonoids, phenolic acids, alkaloids, monoterpenes, iridoids, triterpenes, phenylethanoid glycosides, anthraquinones and other miscellaneous compounds were identified, respectively. Eleven important components, 47 key targets and 15 related pathways based on network pharmacology analysis were obtained. Molecular docking simulation indicated that ERK1/2, c-Fos and p65 might play an essential role in QYD against AP. Finally, the western blot experiments showed that QYD could up-regulate the expression level of ERK1/2 and c-Fos, while down-regulate the expression level of p65.Conclusion: This study predicted and validated that QYD may treat AP by inhibiting inflammation and promoting apoptosis, which provides directions for further experimental studies.

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The bioisosteric modification of pyrazinamide derivatives led to potent antitubercular agents: Synthesis via click approach and molecular docking of pyrazine-1,2,3-triazoles

Cited by 45 publications

References 36 publications

New Pyrazine Conjugates: Synthesis, Computational Studies, and Antiviral Properties against SARS‐CoV‐2

New Pyrazine Conjugates: Synthesis, Computational Studies, and Antiviral Properties against SARS‐CoV‐2

Seeking potent anti-tubercular agents: design and synthesis of substituted-N-(6-(4-(pyrazine-2-carbonyl)piperazine/homopiperazine-1-yl)pyridin-3-yl)benzamide derivatives as anti-tubercular agents

Qing-Yi Decoction in the Treatment of Acute Pancreatitis: An Integrated Approach Based on Chemical Profile, Network Pharmacology, Molecular Docking and Experimental Evaluation

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