Synthesis, Computational, and Photophysical Probing Interactions of Novel Isatin‐Incorporated Thiazolyl‐Coumarins as Potent Antitubercular Agents

ChemistrySelect, Год журнала: 2025, Номер 10(10)

Опубликована: Март 1, 2025

Abstract In this work, we reported the synthesis of a novel series isatin‐incorporated thiazolyl‐coumarin derivatives 4(a–h) by one‐pot three‐component reaction substituted isatin, thiosemicarbazide, and 3‐(2‐bromoacetyl) coumarin. The structures coumarin‐thiazole scaffolds were precisely established their IR, NMR, HRMS spectral data. UV–Vis absorption study target molecules was investigated in six different solvents. Geometrical optimization, molecular electrostatic potential regions, quantum chemical parameters assessed using density functional theory (DFT) to explore electronic properties derivatives. synthesized compounds screened for vitro antimycobacterial activity against Mycobacterium tuberculosis ; all exhibited excellent antitubercular efficacy with MIC ≤ 3.25 µg/mL; among them, 4c 4f most potent 1.56 µg/mL. Furthermore, silico docking analyses enoyl‐ACP reductase (InhA) enzyme conducted; ligands demonstrated favorable binding interactions within active site InhA enzyme.

Язык: Английский

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Synthesis and In vitro Screening of Pyrazine-2-Carbohydrazide Derivatives as Potential Antimicrobial Agents

Journal of Computational Biophysics and Chemistry, Год журнала: 2024, Номер 23(04), С. 541 - 560

Опубликована: Фев. 25, 2024

Herein, we report the design of a new set pyrazine-2-carbohydrazide derivatives (T1–T20) and in silico investigations to evaluate their inhibition activity against enzyme, decaprenylphosphoryl-[Formula: see text]-D-ribose 2 ′ -epimerase (DprE1). The interact with Cys387 residue enzyme’s active site through hydrogen bonds. Further, synthesized these compounds evaluated efficacy M. tuberculosis H37Rv strain. Compounds T16 T19 displayed promising antitubercular activity, boasting minimal inhibitory concentration 1.56 [Formula: text]g/mL. Furthermore, assessed antibacterial range pathogens, including S. aureus, mutans, E. coli text]Typhi. Additionally, antifungal potency A. niger. Notably, T4, T8, T9, exhibited noteworthy tested bacterial strains. T16, T17, T18 showed significant Importantly, all demonstrated low cytotoxicity, IC 50 values exceeding 300 text]M, ensuring no harm normal cells. To gain deeper understanding compounds, conducted pharmacokinetics pharmacochemical properties. employed DFT studies explore electronic characteristics providing valuable insights into potential applications pharmaceutical field.

Язык: Английский

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Synthesis, Characterization, Computational, and Photophysical Investigation of Novel Pyran‐Azo Bridged Benzothiazoles and Their Biological Studies

ChemistrySelect, Год журнала: 2025, Номер 10(13)

Опубликована: Апрель 1, 2025

Abstract In this study, we reported the synthesis of novel heterocyclic azo dyes 4(a‐h) by conventional diazo‐coupling reaction 4‐hydroxy‐6‐methyl‐2‐pyrone with various benzothiazole amines. The molecular structures target molecules were precisely assessed using different spectroscopic (FT‐IR, NMR, and HRMS) studies. Through density functional theory (DFT) geometry, frontier orbitals, global reactivity parameters, electrostatic potential regions investigated to explore electronic properties dyes. in vitro antimycobacterial screening compounds was tested against M. tuberculosis , results showed that 4b 4e exhibited promising activity MIC 3.25 µg mL −1 . Compound significant S. aureus mutans values 0.0195 0.625 mg respectively. Compounds similar sensitivity fungal strain A. niger a silico docking study conducted receptor enoyl‐ACP reductase evaluate binding affinity compounds; derivatives highest scores −9.2 −9.1 kcal mol Furthermore, active low cytotoxicity, none them posed harm normal cells.

Язык: Английский

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Synthesis and characterization of novel N-(2-(pyrazin-2-yl-oxy)ethyl)-4-(trifluoromethoxy)benzamide scaffolds, and biological evaluation and molecular docking studies

RSC Advances, Год журнала: 2025, Номер 15(22), С. 17290 - 17301

Опубликована: Янв. 1, 2025

A new series of biologically potent N -(2-(6-substituted-1 H -pyrazin-2-yloxy)ethyl)-4-(trifluoromethoxy)benzamide scaffolds was synthesized, and their structures were confirmed by 1 NMR, 13 C mass spectrometry.

Язык: Английский

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Synthesis, Computational, and UV-Vis Absorption Studies of Novel Benzothiazole Azo Derivatives and Their Biological Potentials

Russian Journal of Bioorganic Chemistry, Год журнала: 2025, Номер 51(3), С. 1233 - 1248

Опубликована: Июнь 1, 2025

Язык: Английский

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Synthesis and biological evaluation of novel hybrid compounds bearing pyrazine and 1,2,4-triazole analogues as potent antitubercular agents

RSC Pharmaceutics, Год журнала: 2024, Номер 1(2), С. 283 - 295

Опубликована: Янв. 1, 2024

In this study, we synthesized a series of hybrid compounds (T1–T18) containing pyrazine and 1,2,4-triazole moiety assessed their effectiveness against mycobacterium tuberculosis .

Язык: Английский

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Synthesis, computational and UV–Vis absorption studies of novel sulfathiazole azo sulfonamides acting as potent antitubercular agents

Journal of Molecular Structure, Год журнала: 2024, Номер 1319, С. 139358 - 139358

Опубликована: Июль 20, 2024

Язык: Английский

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Noncovalent inhibitors of DprE1 for tuberculosis treatment: design, synthesis, characterization, in vitro and in silico studies of 4-oxo-1,4-dihydroquinazolinylpyrazine-2-carboxamides

Journal of Biomolecular Structure and Dynamics, Год журнала: 2024, Номер unknown, С. 1 - 15

Опубликована: Ноя. 15, 2024

In this study, we present a novel series of 4-oxo-1,4-dihydroquinazolinylpyrazine-2-carboxamide derivatives, which exert their inhibitory effect on decaprenylphosphoryl-β-D-ribose 2'-epimerase (DprE1)

Язык: Английский

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