Synthesis and antimicrobial evaluation of some novel sulfonylamido-benzoxazoles

Temiz-Arpacı, Özlem; Doğanc, Fatma; Sac, Duygu; Sarı, Elmas; Kaynak-Onurdag, Fatma; Ökten, Suzan

doi:10.1556/018.67.2016.1.6

Cited by 4 publications

(3 citation statements)

References 16 publications

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“…Targeted compounds were synthesized treating 5-amino-2-(p-substitutedphenyl)benzoxazoles with appropriate p-substituted phenylacetylchlorides or p-substituted phenylsuphonylchlorides. [36][37] They reported that almost all the synthesized compounds exhibited good inhibitory activity to AChE and BChE enzymes, and moreover, they obtained activity close to that of the reference drug, galantamine. Compound 8a-m was a wide activity range with inhibition values of 6.80-90.21%.…”

Section: Benzimidazoles and Benzoxazoles In Alzheimer's Disease Treat...mentioning

confidence: 95%

“…synthesized a series of new benzoxazole rings and investigated the ChEI activity, since benzoxazoles are structural isosteres of natural nucleotides and easily interact with biopolymers. Targeted compounds were synthesized treating 5‐amino‐2‐(p‐substitutedphenyl)benzoxazoles with appropriate p‐substituted phenylacetylchlorides or p‐ substituted phenylsuphonylchlorides [36–37] . They reported that almost all the synthesized compounds exhibited good inhibitory activity to AChE and BChE enzymes, and moreover, they obtained activity close to that of the reference drug, galantamine.…”

Section: Benzimidazoles and Benzoxazoles In Alzheimer's Disease Treat...mentioning

confidence: 99%

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Benzimidazole and Benzoxazole Derivatives Against Alzheimer's Disease

Faydalı,

Arpacı

2024

Chemistry & Biodiversity

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Benzimidazole and benzoxazole derivatives are included in the category of medical drugs in a wide range of areas such as anticancer, anticoagulant, antihypertensive, anti‐inflammatory, antimicrobial, antiparasitic, antiviral, antioxidant, immunomodulators, proton pump inhibitors, hormone modulators, etc. Many researchers have focused on synthesizing more effective benzimidazole and benzoxazole derivatives for screening various biological activities. In addition, there are benzimidazole and benzoxazole rings as bioisosteres of aromatic rings found in drugs used in the treatment of Alzheimer's disease. Because of the diverse activity of the benzimidazole and benzoxazole rings and bioisosteres marketed as drugs for Alzheimer Diseases, designed compounds containing these rings are likely to be effective against Alzheimer's disease. In this study, the effectiveness of compounds containing benzimidazole and benzoxazole rings against Alzheimer's disease will be examined.

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Section: Benzimidazoles and Benzoxazoles In Alzheimer's Disease Treat...mentioning

confidence: 95%

Section: Benzimidazoles and Benzoxazoles In Alzheimer's Disease Treat...mentioning

confidence: 99%

Benzimidazole and Benzoxazole Derivatives Against Alzheimer's Disease

Faydalı,

Arpacı

2024

Chemistry & Biodiversity

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“…The N2-N8 series was synthesized in our work following the procedure described in the literature, as shown in Figure 1 [22,23]. Initially, 5-Amino-2-(4-tert-butylphenyl)benzoxazole was obtained by reaction of 2,4-diaminophenol with 4-tert-butylbenzoic acid in PPA.…”

Section: Chemistrymentioning

confidence: 99%

New Sulfonamido-Benzoxazole Derivatives as Antimicrobial Agents: Design, Synthesis and Biological Evaluation

EROL,

ACAR-HALICI,

KUYUCUKLU

et al. 2023

Ankara Ecz. Fak. Derg.

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Objective: Many investigations are conducted in the battle against infectious diseases in order to develop new drug-active ingredient candidate compounds and to identify leading compounds. The goal of this study was to synthesis a total of seven compounds, six of which are novel, with the general structure 2-(4-tert-butylphenyl)-5-(4-substitutedphenylsulfonamido)benzoxazole, to elucidate their structures, and to test their antimicrobial activities using the microdilution method. Material and Method: The synthesis of the compounds was carried out in two stages. In the first stage, under PPA catalyst 2,4-diaminophenol and 4-tert-butylbenzoic acid were refluxed, and target compounds were produced in the second step by reacting 4-substitutedbenzenesulfonyl chloride with 5-Amino-2-(4-tert-butylphenyl)benzoxazole. The compounds' antimicrobial activity was determined by using Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Candida albicans, and drug-resistant strains of these microorganisms in vitro antimicrobial activity studies. Furthermore, estimated ADME profiles were calculated using the SwissADME online software. Result and Discussion: The structures of the synthesized compounds were elucidated using 1H-NMR, 13C-NMR and Mass spectroscopy, and also their melting points were determined. The antimicrobial activities of the compounds ranged from 64 µg/ml to ˃512 µg/ml and were weaker than the reference drugs. The best antimicrobial activity was reported against an isolate of E. faecalis, with all compounds having MIC values of 64 µg/ml. The fact that six of the seven synthesized compounds are novel and that their antimicrobial activity will be tested for the first time will make a significant contribution to studies to develop new or alternative antimicrobial agents.

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Novel Sulfonylamido Benzoxazole Derivatives: Synthesis, Characterisation, Molecular Docking, DFT, and Antimicrobial Activity Investigations

Faydali,

Erol,

Temiz Arpaci

et al. 2024

Chemistry & Biodiversity

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In this work, numerous novel 2‐(p‐substitutedphenyl)‐5‐[(p‐substitutedphenyl)sulfonylamido]benzoxazole derivatives were designed, synthesized, and structurally characterized using mass spectroscopy, 1H‐NMR, 13C‐NMR, and elemental analysis approaches. The antimicrobial activity against several Gram (+), Gram (‐), and fungal species was determined using the in vitro microdilution technique. A molecular docking analysis was performed on all produced compounds utilizing the S. aureus Gyrase complex with Ciprofloxacin and DNA. Two of the most effective compounds against S. aureus, N4 and N9, have binding energies of ‐8.7 kcal/mol and ‐8.6 kcal/mol, respectively, and their interactions have been demonstrated in 2D and 3D. Furthermore, utilizing the 6‐311G(d,p) base set and DFT/B3LYP theory, MEP analysis, geometric optimization, and molecular reactivity analysis (HOMO‐LUMO) of N4 and N9 were performed, and the results were presented. All compounds' theoretical ADMET profiles were computed as well, and they met Lipinski and other strict criteria. With all of this knowledge, this study could be a pioneer in the development of novel anti‐S. aureus compounds.

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Synthesis and antimicrobial evaluation of some novel sulfonylamido-benzoxazoles

Cited by 4 publications

References 16 publications

Benzimidazole and Benzoxazole Derivatives Against Alzheimer's Disease

Benzimidazole and Benzoxazole Derivatives Against Alzheimer's Disease

New Sulfonamido-Benzoxazole Derivatives as Antimicrobial Agents: Design, Synthesis and Biological Evaluation

Novel Sulfonylamido Benzoxazole Derivatives: Synthesis, Characterisation, Molecular Docking, DFT, and Antimicrobial Activity Investigations

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