Design, synthesis and biological evaluation of novel 2-(5-aryl-1H-imidazol-1-yl) derivatives as potential inhibitors of the HIV-1 Vpu and host BST-2 protein interaction

Rashamuse, Thompo J.; Njengele, Zikhona; Coyanis, E. Mabel; Sayed, Yasien; Mosebi, Salerwe; Bode, Moira L.

doi:10.1016/j.ejmech.2020.112111

Cited by 12 publications

(7 citation statements)

References 64 publications

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“…The cytotoxicity of the compounds was evaluated by the inhibition of MTT reduction into formazan and by the trypan blue staining assay. 39 Briefly, in the MTT assay, A549 cells were seeded in 96-well plates at a density of 2 × 10 4 cells per well in 100 μL of complete DMEM without phenol red for 24 h at 37 °C. Subsequently, cell monolayers were treated or not with increasing concentrations (range 5–80 μg mL −1 ) of compounds for 24 h at 37 °C.…”

Section: Methodsmentioning

confidence: 99%

Aminomalononitrile inspired prebiotic chemistry as a novel multicomponent tool for the synthesis of imidazole and purine derivatives with anti-influenza A virus activity

et al. 2021

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Section: Methodsmentioning

confidence: 99%

Aminomalononitrile inspired prebiotic chemistry as a novel multicomponent tool for the synthesis of imidazole and purine derivatives with anti-influenza A virus activity

et al. 2021

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“…Explicit confirmation for the structures of 13a, 13b, 13d and 8 was obtained from single-crystal X-ray analysis (Figure 3). These compounds were prepared as part of our ongoing efforts towards identifying novel heterocycles with biological activity [46][47][48]. Compounds showing cytotoxicity values of >200 µM in MT-4 cells were evaluated for activity in an HIV assay (see Supplementary Materials).…”

Section: Synthesis Of 5h-thiazolo[32-a]pyrimidine-7-carboxylates Using Two-component and Three-component Reactionsmentioning

confidence: 99%

“…For mass spectrometry (LC-MS/MS), highresolution mass spectra were obtained. Fourier infrared spectra (FTIR) were recorded by These compounds were prepared as part of our ongoing efforts towards identifying novel heterocycles with biological activity [46][47][48]. Compounds showing cytotoxicity values of >200 µM in MT-4 cells were evaluated for activity in an HIV assay (see Supplementary Materials).…”

Section: General Informationmentioning

confidence: 99%

Synthesis of 6-Membered-Ring Fused Thiazine-Dicarboxylates and Thiazole-Pyrimidines via One-Pot Three-Component Reactions

et al. 2021

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A facile and efficient one-pot three-component reaction method for the synthesis of thiazine-dicarboxylates is reported. Reaction of an isocyanide and dialkyl acetylenedicarboxylate with 2-amino-4H-1,3-thiazin-4-one derivatives containing both an acidic proton and an internal nucleophile gave the products in good yields of 76–85%. The reactivity of dialkyl acetylenedicarboxylates was further tested in the synthesis of thiazole-pyrimidines where a two-component reaction of 2-aminothiazole with dialkyl acetylenedicarboxylates was successfully converted to a more efficient three-component reaction of a thiourea, α-haloketone and dialkyl acetylenedicarboxylate (DMAD/DEtAD) to give thiazole-pyrimidines in good yields of 70–91%.

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“…Of particular interest is the disruption of interactions between HIV-1-proteins and host proteins. [1][2][3][4][5][6] Computational modelling was used as a strategy to identify scaffolds as the starting point to derive small molecules that could possibly disrupt interactions between HIV-1 integrase (HIV-1-IN) and host lens epithelium-derived growth factor (LEDGF/p75) proteins. Virtual screening of the ChemBridge Diverset library of compounds (consisting of 20,000 diverse and unique drug-like structures) was performed using Schrödinger Maestro 11.2 software.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Hexahydroquinoline-3-carboxamide Derivatives and Their HIV-1 Antiviral Activity

Bode¹,

Coyanis²,

Mohlala³

et al. 2022

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Computational modelling was used to identify scaffolds with the potential to disrupt the interaction between HIV-1 integrase and lens epitheliumderived growth factor (HIV-1-IN-LEDGF/p75). Virtual screening of commercial library collections led to the identification of N-(4-chlorophenyl)-7,7-dimethyl-2,5dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxamide as a promising candidate.The synthesis of this compound and its derivatives involved the reaction of the corresponding carboxylic acid derivatives with aniline in the presence of coupling agent carbonyldiimidazole (CDI). This gave rise to N-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxamides in yields of 71-85% . These compounds were found to be non-toxic in an MT4 cell line at 100 μM and were subsequently evaluated for antiviral activity in infected MT4 cells at a single dose concentration of 100 μM.

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Design, synthesis and biological evaluation of novel 2-(5-aryl-1H-imidazol-1-yl) derivatives as potential inhibitors of the HIV-1 Vpu and host BST-2 protein interaction

Cited by 12 publications

References 64 publications

Aminomalononitrile inspired prebiotic chemistry as a novel multicomponent tool for the synthesis of imidazole and purine derivatives with anti-influenza A virus activity

Aminomalononitrile inspired prebiotic chemistry as a novel multicomponent tool for the synthesis of imidazole and purine derivatives with anti-influenza A virus activity

Synthesis of 6-Membered-Ring Fused Thiazine-Dicarboxylates and Thiazole-Pyrimidines via One-Pot Three-Component Reactions

Synthesis of Hexahydroquinoline-3-carboxamide Derivatives and Their HIV-1 Antiviral Activity

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