CuAAC Mediated Synthesis of 2‐HBT Linked Bioactive 1,2,3‐Triazole Hybrids: Investigations through Fluorescence, DNA Binding, Molecular Docking, ADME Predictions and DFT Study

Nehra, Nidhi; Tittal, Ram Kumar; Ghule, Vikas D.; Kumar, Nikhil; Paul, Avijit Kumar; Lal, Kashmiri; Kumar, Awanish

doi:10.1002/slct.202003919

Cited by 16 publications

(14 citation statements)

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“…1,2,3-Triazole hybrid molecules were then synthesized using the CuAAC reaction of as formed organic azide and alkyne precursors . The resulting 1,2,3-triazole molecules were purified using silica gel column chromatography in good-to-high yields.…”

Section: Resultsmentioning

confidence: 99%

“…33 1,2,3-Triazole hybrid molecules were then synthesized using the CuAAC reaction of as formed organic azide and alkyne precursors. 7 The resulting 1,2,3-triazole molecules were purified using silica gel column chromatography in good-tohigh yields. Detailed experimental procedures and various characterization data of 6a−l are given in a Supporting Information (SI) file.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Ligand and receptor preparation by adding Gasteiger charges followed by the removal of water molecules and addition of polar hydrogens were performed using AutoDockTools-1.5.6 software. Calculations and simulations were performed in the AutoDock Vina program, and result visualization was performed using the Discovery studio visualizer. , …”

Section: Experimental Sectionmentioning

confidence: 99%

“…1,2,3-Triazoles possess significant chemical properties such as aromatic stability, resistance to acid–base hydrolysis, high dipole moment, and the ability to form H-bonds. , Triazoles have been used as precursors in the synthesis of various pharmaceutical drugs of medicinal use, and they also play important roles in organic synthetic chemistry. 1,2,3-Triazoles exhibit peculiar biological properties such as antibacterial, − antitubercular, anti-inflammatory, antifungal, , antiallergic, and anticancer properties. ,,− The triazole moiety readily associates with biological targets such as DNA via H-bonds and other noncovalent interactions, improving solubility and metabolic stability . In the past few decades, various metal-catalyzed synthetic methods have been developed for triazole synthesis.…”

Section: Introductionmentioning

confidence: 99%

“…2,3 Triazoles have been used as precursors in the synthesis of various pharmaceutical drugs of medicinal use, and they also play important roles in organic synthetic chemistry. 1,2,3-Triazoles exhibit peculiar biological properties such as antibacterial, 4−6 antitubercular, 4 anti-inflammatory, 4 antifungal, 7,8 antiallergic, 9 and anticancer properties. 2,4,10−12 The triazole moiety readily associates with biological targets such as DNA via H-bonds and other noncovalent interactions, improving solubility and metabolic stability.…”

Section: ■ Introductionmentioning

confidence: 99%

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1,2,3-Triazoles of 8-Hydroxyquinoline and HBT: Synthesis and Studies (DNA Binding, Antimicrobial, Molecular Docking, ADME, and DFT)

2021

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A new series of 1,2,3-triazole hybrids containing either 2- or 4-hydroxyphenyl benzothiazole (2- or 4-HBT) and naphthalen-1-ol or 8-hydroxyquinoline (8-HQ) was synthesized in high yields and fully characterized. In vitro DNA binding studies with herring fish sperm DNA (hs-DNA) showed that quinoline- and 2-HBT-linked 1,2,3-triazoles of shorter alkyl linkers such as 6a are better with a high binding affinity (3.90 × 105 L mol–1) with hs-DNA as compared to naphthol- and 4-HBT-linked 1,2,3-triazoles bound to longer alkyl linkers. Molecular docking of most active 1,2,3-triazoles 6a–f showed high binding energy of 6a (−8.7 kcal mol–1). Also, compound 6a displayed considerable antibacterial activity and superior antifungal activity with reference to ciprofloxacin and fluconazole, respectively. The docking results of the fungal enzyme lanosterol 14-α-demethylase showed high binding energy for 6a (−9.7 kcal mol–1) involving dominating H-bonds, electrostatic interaction, and hydrophobic interaction. The absorption, distribution, metabolism, and excretion (ADME) parameter, Molinspiration bioactivity score, and the PreADMET properties revealed that most of the synthesized 1,2,3-triazole molecules possess desirable physicochemical properties for drug-likeness and may be considered as orally active potential drugs. The electrophilicity index and chemical hardness properties were also studied by density functional theory (DFT) using the B3LYP/6-311G(d,p) level/basis set.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Experimental Sectionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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1,2,3-Triazoles of 8-Hydroxyquinoline and HBT: Synthesis and Studies (DNA Binding, Antimicrobial, Molecular Docking, ADME, and DFT)

2021

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Synthesis, Biological Evaluation, Molecular Docking, and Acid Dissociation Constant of New Bis‐1,2,3‐triazole Compounds

et al. 2021

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In this study, new bis-1,2,3-triazole derivatives, N,N'-(1,3phenylene)bis(2-(4-R-1H-1,2,3-triazol-1-yl)acetamide), were synthesized by copper-catalyzed azide-alkyne cycloaddition click chemistry in 84-96 % yield. A wide range bioactivity screening was performed to determine DNA cleavage, antioxidant, antibacterial and antifungal activities. All of the synthesized bis-1,2,3-triazoles showed excellent DNA cleavage activity and 4 e, bearing 2-bromoethyl moiety as a substituent, was almost degraded all of the plasmid DNA. Molecular docking simulations suggest that the synthesized compounds act as minor groove binders of DNA. The antioxidant activities of the bis-1,2,3-triazoles were determined based on the radical scavenging effect of the stable 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical and iron chelating activity. The compounds exhibited effective iron chelating activity at 200 mg/L while showing a moderate ability to scavenge DPPH radical. The compounds exhibited antibacterial activity against B. cereus, L. pneumophila subsp. pneumophila, S. aureus, P. aeruginosa, E. coli and E. hirae bacterial strains, and antifungal activity against C. albicans and C. tropicalis microfungus strains with a MIC value in the range of 4-128 μg/mL. 4 d, bearing cyclohexylmethyl moiety as substituent, exhibited a broadspectrum antimicrobial activity (both antibacterial and antifungal). Four different acid dissociation constant (pK a ) values of each product were determined potentiometrically in 20 % (v/v) dimethyl sulfoxide-water at 25 � 0.1°C, at an ionic background of 0.1mol/L of NaCl using the HYPERQUAD program.

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Benzothiazole‐Hydrazone Chromophores: Synthesis, Solvatochromism, Computational and Antimycobacterial Activity Studies

Basavaraju

Pasha

et al. 2023

ChemistrySelect

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Coumarin and its heterocyclic derivatives have been receiving tremendous attention from synthetic and medicinal chemists owing to their remarkable application in material science as well as pharmacological applications. In the current study, a series of coumarin-coupled benzothiazole hydrazone compounds were synthesized by a two-step process, post which their structural features were investigated with the aid of various spectroscopic techniques. The novel synthesized chromophores displayed an electronic absorption band in a range of 358-428 nm and exhibited a positive solvatochromism character as well as a high molar absorption coefficient in the studied solvents. HOMO-LUMO gap, quantum parameters, and various other pharmacokinetics and ADME-T properties of these compounds were investigated through the computational approach. Biological activity assays revealed that all compounds displayed excellent antibacterial activity compared to the Amoxicillin and have also been studied for their antimycobacterial efficacy against Mycobacterium tuberculosis. Furthermore, molecular docking studies was performed with enoyl-acyl carrier protein reductase (InhA).

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CuAAC Mediated Synthesis of 2‐HBT Linked Bioactive 1,2,3‐Triazole Hybrids: Investigations through Fluorescence, DNA Binding, Molecular Docking, ADME Predictions and DFT Study

Cited by 16 publications

References 61 publications

1,2,3-Triazoles of 8-Hydroxyquinoline and HBT: Synthesis and Studies (DNA Binding, Antimicrobial, Molecular Docking, ADME, and DFT)

1,2,3-Triazoles of 8-Hydroxyquinoline and HBT: Synthesis and Studies (DNA Binding, Antimicrobial, Molecular Docking, ADME, and DFT)

Synthesis, Biological Evaluation, Molecular Docking, and Acid Dissociation Constant of New Bis‐1,2,3‐triazole Compounds

Benzothiazole‐Hydrazone Chromophores: Synthesis, Solvatochromism, Computational and Antimycobacterial Activity Studies

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