Synthesis and antimicrobial evaluation of some novel sulfonylamido-benzoxazoles

A series of 2-(p-substituted phenyl)-5-[(4-substituted phenyl) sulfonylamido]-benzoxazoles were synthesized and tested for their antimicrobial activities. The structures of the new derivatives were elucidated by spectral techniques. The minimum inhibitory concentrations (MIC) of the new benzoxazoles were determined against standard bacterial and fungal strains and drug-resistant isolates and compared to those of several reference drugs

Synthesis and the effect of a novel benzoxazole compound on breast cancer cell line

Breast cancer today is the most frequent cancer among women, and the second most common cause of cancer deaths among women. The aim of this study was to synthesize a new benzoxazole derivative, scan it for anti-cancer potential by MTT test using different breast cancer cell lines, and examine its effects on NF-κB and apopitosis-related proteins (APAF-1, cytochrome C, caspase-3, bcl-2) by the western blot method. newly-synthesized benzoxazole compound was applied to breast cancer cell lines (MDA-MB, MCF-7) and its cytotoxicity was measured quantitatively by MTT test. Later, the level of its effects on NF-κB and apopitosis-related proteins (APAF-1, cytochrome C, caspase-3, bcl-2) were examined by the western blot method. In our study, the structure of the synthesized new 5-[4-chlorobutanamido]-2-(p-methylphenyl)benzoxazole was proved by elemental analysis, 1H NMR and mass spectroscopy analysis methods. When the toxic effects of the application of the compound on the cell lines was examined by MTT, it had a greater toxic effect on MCF-7 when compared with MDA-MB, and IC50 levels were lower. When the protein was examined in immunohistochemistry with regard to VEGF, eNOS and TUNEL, it was observed that it caused a reduction in VEGF and an increase in eNOS and TUNEL. In the assay of the proteins by western blot, when benzoxazole compound was added to the MDA and MCF-7 cell line, there was no difference from the control group in Apaf-1 and BCL-2 levels, but a reduction was observed in caspase and Nfkβ levels compared with the control group. When the compound was added to the MDA-MB cell line, an increase was shown in the Cytochrome C level compared to the control group, but no difference was seen in the MCF-7 cell line. It is felt that this synthesized new benzoxazole compound increases apopitosis by reducing the activation of Nfkβ, and in this way has shown an effect of inhibiting tumor growth in cancer treatment. In addition, it is felt that this can provide hope in cancer treatment by the improved phase studies. [Med-Science 2019; 8(1.000): 186-91

Synthesis and antimicrobial evaluation of novel 5-substituted-2-(p-tert-butylphenyl)benzoxazoles

In the present study, a series of nine novel 5-substituted-2-(p-tert-butylphenyl)benzoxazole derivatives have been synthesized and their structures confirmed by spectral techniques and also tested for their antimicrobial activities. The minimum inhibitory concentrations (MIC) of the new benzoxazoles have been determined against standard bacterial and fungal strains and drug-resistant isolates and compared to those of several reference drugs. The new benzoxazole derivatives are found to possess a broad spectrum of antibacterial activity with MIC values of 8-256 mu g/mL. Especially, compound 9 is more active than standard drugs ciprofloxacin and cefotaxime against E. coli isolate with a MIC value of 8 mu g/mL. Also new compounds are less active than fluconazole with a MIC value of 256 mu g/mL against C. albicans and its isolate except for compound 9 that shows better activity other compounds with a MIC value of >4 mu g/mL for their antifungal activity

Synthesis and antimicrobial evaluation of novel 5-substituted-2-(<em>p</em>-tert-butylphenyl)benzoxazoles

385-389In the present study, a series of nine novel 5-substituted-2-(p-tert-butylphenyl)benzoxazole derivatives have been synthesized and their structures confirmed by spectral techniques and also tested for their antimicrobial activities. The minimum inhibitory concentrations (MIC) of the new benzoxazoles have been determined against standard bacterial and fungal strains and drug-resistant isolates and compared to those of several reference drugs. The new benzoxazole derivatives are found to possess a broad spectrum of antibacterial activity with MIC values of 8−256 µg/mL. Especially, compound 9 is more active than standard drugs ciprofloxacin and cefotaxime against E. coli isolate with a MIC value of 8 µg/mL. Also new compounds are less active than fluconazole with a MIC value of 256 µg/mL against C. albicans and its isolate except for compound 9 that shows better activity other compounds with a MIC value of >4 µg/mL for their antifungal activity

Synthesis of some piperazinobenzoxazole derivatives and their antimicrobial properties

240-247<span style="font-size:11.0pt;mso-bidi-font-size: 10.0pt;font-family:" times="" new="" roman";mso-fareast-font-family:"times="" roman";="" mso-bidi-font-family:"times="" roman";letter-spacing:-.2pt;mso-ansi-language:="" en-us;mso-fareast-language:en-us;mso-bidi-language:ar-sa"="" lang="EN-US">A series of 2-(p-substitutedphenyl/benzyl)-5-[3-[4-[(p-chlorophenyl)/phenyl]piperazin-1-yl]propionamido]-benzoxazoles (<b style="mso-bidi-font-weight: normal">3-22) have been synthesized towards discovering new antimicrobial compounds in order to fight against pathogens, which have become resistant to antibiotics and are the cause of increased mortality and morbidity throughout the world. Structures of new derivatives have been elucidated by spectral techniques. New and previously synthesized benzoxazoles have been evaluated for their antibacterial and antifungal activity against standard strains, and their drug-resistant isolates in comparison with reference drugs. This study is aimed to investigate the efficacy of the antimicrobial effect of different amido bridges on the same homologue structures of benzoxazole compounds. Compounds 3-22 exhibit broad antibacterial activity with MIC (Minimum Inhibitory Concentration) values of 128-256 µg/mL against Staphylococcus aureus and its isolate except for derivative <b style="mso-bidi-font-weight: normal">7 that has a MIC value of 32 µg/mL against S. aureus isolate and compounds 3 and <b style="mso-bidi-font-weight: normal">22 which have <span style="font-size:11.0pt; mso-bidi-font-size:9.0pt;font-family:" times="" new="" roman";mso-fareast-font-family:="" "times="" roman";mso-bidi-font-family:"times="" roman";mso-ansi-language:="" en-us;mso-fareast-language:en-us;mso-bidi-language:ar-sa"="" lang="EN-US">MIC value of 512 µg/mL against S. aureus. Also, t<span style="font-size:9.0pt; font-family:" times="" new="" roman";mso-fareast-font-family:"arial="" unicode="" ms";="" mso-bidi-font-family:"times="" roman";mso-ansi-language:en-us;font-weight:="" normal"="" lang="EN-US">he tested compounds 3-22 possess low antifungal activity with MIC values of 128 µg/mL against Candida albicans in comparison with antifungal reference drugs, fluconazole and amphotericin B.</span

Design, synthesis, molecular docking, density functional theory and antimicrobial studies of some novel benzoxazole derivatives as structural bioisosteres of nucleotides

A series of some novel 2-(p-tert-butylphenyl)-5-(3-substituted-propionamido)benzoxazole derivatives have been designed, synthesized, evaluated for antimicrobial activity and have performed molecular docking studies against penicillin-binding protein 4 (PBP4) and active and allosteric site of PBP2a; were calculated some theoretical quantum parameters and absorption, distribution, metabolism and excretion (ADME) descriptors. B9 acted at minimum inhibitory concentration (MIC) = 8 mu g/mL against S. aureus, E. faecalis and their drug-resistant isolates and also formed with GLU145 (1.74 angstrom) and ILE144 (1.89 angstrom) two hydrogen bonds at allosteric site of PBP2a with Glide emodel score: -42.168. Delta E of compound B9 had moderate value of all compounds with 0.14742

DFT, docking, MD simulation, and vibrational spectra with SERS analysis of a benzoxazole derivative: an anti-cancerous drug

Spectroscopic, DFT, and SERS studies of antimicrobial bioactive 2-(p-bromophenyl)-5-(2-(4-(p-chlorophenyl)piperazine-1-yl)acetamido)benzoxazole (BCAB) have been reported. Very large changes are seen wavenumbers in Raman and SERS. Variations in modes may be due to surface pi-electron interactions and means, the BACB is inclined with respect to the metal surface. Theoretical molecular geometry optimization parameters, wavenumbers, frontier molecular orbitals, and molecular electrostatic potential surface have been calculated using density functional theory. The docked ligand forms a stable complex with SOCS-2 and can be BCAB may be an anti-cancerous drug. According to RMSD, RMSF, and Rg analysis, BACB and SOCS-2 protein form a stable and stable interaction

Synthesis, molecular docking and ADME prediction of some new benzimidazole carboxamidines derivatives as antimicrobial agents

In this study, 15 new 1H-benzimidazole-5-carboxamidine derivative compounds that could be new antimicrobial agents were synthesized and their antimicrobial activities were determined using the microdilution method. When the activity results were examined, it was observed that the antibacterial effects of the new benzimidazole derivatives were weaker than standard drugs, but some derivatives showed significant efficacy against MRSA and VREF with the value of MIC: 8 mu g/ml compared to reference drugs. The antifungal effects of the compounds were found to be weaker compared to the reference drugs. Molecular docking studies of compounds and reference drugs used were performed against PBP4 and the active and allosteric site of PBP2a, and estimated ADME profiles were calculated. In addition, 2D and 3D interactions of N10, one of the most effective antimicrobial compounds compared to reference drugs, were demonstrated in both sites

1H-Benzimidazole-5-carboxamidine derivatives: design, synthesis, molecular docking, DFT and antimicrobial studies

In this study, 15 new N-(cyclohexyl)-2-substituted-1H-benzimidazole-5-carboxamidine derivatives that could be new antimicrobial agents were synthesized and their antimicrobial activities were determined using the microdilution method. Some of the derivatives showed significant efficacy against MRSA and VREF with an MIC value of 8 mu g mL(-1) compared to reference drugs. Molecular docking studies of the compounds against PBP4 and active and allosteric regions of PBP2a were performed and estimated ADME profiles were calculated. The nitrogens of the amidine group of M7, one of the most effective antimicrobial compounds compared to reference drugs, formed two separate hydrogen bonds with ASP275 (1.77 angstrom) and ASP295 (1.83 angstrom) in the allosteric region of PBP2a. Geometric optimization parameters, MEP analysis, and HUMO and LUMO quantum parameters of M7 were calculated using DFT/B3LYP theory and the 6-311G(d,p) basis set and the results are displayed