Synthesis of 1,2,3-triazole-piperazin-benzo[<i>b</i>][1,4]thiazine 1,1-dioxides: antibacterial, hemolytic and <i>in silico</i> TLR4 protein inhibitory activities

Ramu, Nagavelli; Krishna, Thupurani Murali; Kapavarapu, Ravikumar; Narsimha, Sirassu

doi:10.1039/d3ra07509e

RSC Adv.

2024

DOI: 10.1039/d3ra07509e

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Synthesis of 1,2,3-triazole-piperazin-benzo[b][1,4]thiazine 1,1-dioxides: antibacterial, hemolytic and in silico TLR4 protein inhibitory activities

Nagavelli Ramu,

Thupurani Murali Krishna,

Ravikumar Kapavarapu

et al.

Abstract: Novel 1,2,3-triazoles (6a–6j & 8a–8g) were synthesized and evaluated for their antibacterial activity against S. aureus. The more potent compounds were further evaluated for their in silico TLR4 inhibitory activity.

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Cited by 2 publications

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Fused Imidazo[1,2‐d][1,2,4]Thiadiazolo[1,2,3]Triazoles: One‐Pot Synthesis, Anti‐Bacterial, Anti‐Biofilm and TLR4 Inhibitory Activities

Premalatha,

Azam,

Kapavarapu

et al. 2024

ChemistrySelect

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We developed and evaluated several new fused imidazo[1,2‐d][1,2,4]thiadiazolo[1,2,3]triazoles to see how they perform against bacteria and biofilms. Some compounds showed acceptable activity compared to the primary standard, Dicloxacillin. Some of the compounds demonstrated significant antibacterial activity against S. aureus, with MIC values ranging from 1.56–12.5 μg/mL. We also found anti‐biofilm properties in the potent compounds. The results showed that derivatives 3‐(4‐fluorophenyl)imidazo[1,2‐d] [1,2,3] triazolo[1,5‐b][1,2,4]thiadiazole 8,8‐dioxide and 3‐(3,5‐difluorophenyl)imidazo[1,2‐d][1,2,3]triazolo[1,5‐b][1,2,4] thiadiazole 8,8‐dioxide were strong antibacterial agents and effective MSSA and MRSA biofilm growth inhibitors. We conducted in silico studies to assess the molecular interactions of more potent compounds with TLR4 proteins (PDB: 3FXI, 3VQ1, 3RG1). Our findings revealed that 3‐(4‐chloro‐3,5‐dimethoxyphenyl)imidazo[1,2‐d][1,2,3]triazolo[1,5‐b] [1,2,4]thiadiazole 8,8‐dioxide, 3‐(3,5‐dichlorophenyl)imidazo[1,2‐d] [1,2,3]triazolo[1,5‐b][1,2,4] thiadiazole 8,8‐dioxide, and 3‐(4‐(trifluoromethyl)phenyl)imidazo[1,2‐d][1,2,3]triazolo[1,5‐b][1,2,4] thiadiazole 8,8‐dioxide exhibited more binding interactions than dicloxacillin. ADME of more potent compounds examined in this study and compounds could potentially inhibit the cytochrome P450 CYP2C19 isoform.

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Fused Imidazo[1,2‐d][1,2,4]Thiadiazolo[1,2,3]Triazoles: One‐Pot Synthesis, Anti‐Bacterial, Anti‐Biofilm and TLR4 Inhibitory Activities

Premalatha,

Azam,

Kapavarapu

et al. 2024

ChemistrySelect

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Utilizing perhalopyridine-based alkynes as suitable precursors for the synthesis of novel poly(1,2,3-triazolyl)-substituted perhalopyridines

Khorasani,

Ranjbar-Karimi,

Mohammadiannejad

2024

RSC Adv.

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Synthesis of 1,2,3-triazole-piperazin-benzo[b][1,4]thiazine 1,1-dioxides: antibacterial, hemolytic and in silico TLR4 protein inhibitory activities

Abstract: Novel 1,2,3-triazoles (6a–6j & 8a–8g) were synthesized and evaluated for their antibacterial activity against S. aureus. The more potent compounds were further evaluated for their in silico TLR4 inhibitory activity.

Cited by 2 publications

References 40 publications

Fused Imidazo[1,2‐d][1,2,4]Thiadiazolo[1,2,3]Triazoles: One‐Pot Synthesis, Anti‐Bacterial, Anti‐Biofilm and TLR4 Inhibitory Activities

Fused Imidazo[1,2‐d][1,2,4]Thiadiazolo[1,2,3]Triazoles: One‐Pot Synthesis, Anti‐Bacterial, Anti‐Biofilm and TLR4 Inhibitory Activities

Utilizing perhalopyridine-based alkynes as suitable precursors for the synthesis of novel poly(1,2,3-triazolyl)-substituted perhalopyridines

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