Mustafa Arisoy

Synthesis, antimicrobial activity, pharmacophore analysis of some new 2-(substitutedphenyl/benzyl)-5-[(2-benzofuryl)carboxamido]benzoxazoles.

The synthesis and antimicrobial activity of a new series of 2-(substitutedphenyl/benzyl)-5-[(2-benzofuryl)carboxamido]benzoxazole derivatives 3-12 were described. The in vitro antimicrobial activity of the compounds was determined against some Gram-positive, Gram-negative bacteria and fungi and their drug-resistant isolates in comparison with standard drugs. Antimicrobial results indicated that the synthesized compounds possessed a broad spectrum of activity with MIC values 500-15.625 microg/ml. In the series, the most active compound against Candida krusei and Candida albicans isolate is 8 with MIC value 31.25 microg/ml. However, it is one dilution less potent than the compared fluconazole. Some of the screened compounds exhibit significant activity, having MIC value as 31.25 microg/ml in Pseudomonas aeruginosa having same activity as Rifampicin. Furthermore, considering the worth of developing new antibacterial agents against drug-resistant P. aeruginosa the present study explores the structure-activity relationship analysis of 2-(substitutedphenyl/benzyl)-5-[(2-benzofuryl)carboxamido]benzoxazoles using 3D-common features pharmacophore hypotheses approach.

PVA/PAA-Based Antibacterial Wound Dressing Material with Aloe Vera

The incorporation of drugs into the dressings make these dressings antimicrobial and help in control of infection around the wound. The wound dressing materials based on PVA/PAA, ciprofloxacin HCl, and aloe vera have been designed and developed so that the wound undergoes proper healing and scar formation is minimal. These wound dressing materials are produced using the electrospinning method. The wound dressing materials are characterized using the FT-IR, DSC, DTA, TGA, and SEM techniques. The wound dressing materials are tested for microbial activity tests and drug release experiments. Controlled ciprofloxacin HCl release is observed.

Synthesis, FT-IR investigation and computational study of 5-[(4-Bromophenyl)acetamido]-2-(4-tert-butylphenyl) benzoxazole

The synthesis and antimicrobial properties of 5-[(4-Bromophenyl)acetamido]-2-(4-tertbutylphenyl) benzoxazole are reported in the present work. The optimized molecular structure, (1)H NMR, vibrational frequencies, corresponding vibrational assignments of 5-[(4-Bromophenyl)acetamido]-2-(4-tert-butylphenyl) benzoxazole have been investigated experimentally and theoretically using Gaussian09 software package. Potential energy distribution of the normal modes of vibrations was done using GAR2PED program. The HOMO and LUMO analysis is used to determine the charge transfer within the molecule. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. MEP was performed by the SDD method and the predicted infrared intensities have also been reported. The calculated geometrical parameters are in agreement with that of similar derivates. The first hyperpolarizability is high and the title compound is suitable for further NLO studies. Microbiological results indicated that the title compound possessed a broad spectrum activity against the tested Gram-positive, Gram-negative bacteria.

Synthesis, antimicrobial activity and QSAR studies of 2,5-disubstituted benzoxazoles

In this study, a new series of 2,5-disubstituted benzoxazoles was synthesized and their structures were elucidated by elemental analysis, MASS, 1H-NMR, 13C-NMR and IR spectral data. Newly and previously synthesized 2,5-disubstituted benzoxazole derivatives were evaluated for antibacterial and antifungal activity against standard strains and their drug-resistant isolates. Microbiological results showed that the compounds presented a large spectrum of activity having MIC values of 250–7.8 µg mL−1 against the tested microorganisms. Among the newly synthesized derivatives 3–22, compound 11 was the most active against Candida krusei out of all; however, it was one dilution less potent than standard drug fluconazole. In addition, all the new and previous compounds were more active than standard drugs ampicillin trihydrate and rifampicin against Pseudomonas aeruginosa and its gentamicin-resistant isolate. The 2D-QSAR (Quantitative Structure–Activity Relationship) analysis of a set of newly and previously synthesized benzoxazoles tested for growth inhibitory activity against methicillin-resistant Staphylococcus aureus (MRSA) was also performed by using multivariable regression analysis. The activity contributions for substituent effects of these compounds were determined from the correlation equation for predictions of the lead optimization.

Novel Benzoxazoles: Synthesis and Antibacterial, Antifungal, and Antitubercular Activity against Antibiotic-Resistant and -Sensitive Microbes

A new series of 5-(p-substituted benzamido/phenylacetamido)-2-(p-tert-butylphenyl)benzoxazole derivatives were synthesized and evaluated for their antibacterial, antifungal, and antimycobacterial activities against antibiotic-resistant and -sensitive Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, Klebsiella pneumoniae, and Mycobacterium tuberculosis as well as against Candida albicans and Candida krusei. The compounds possessed broad-spectrum activity against all of the tested Gram-positive and Gram-negative bacteria and yeasts, their minimum inhibitory concentrations (MICs) ranging between 16 - 128 μg/ml. One compound exhibited significant antibacterial activity (16 μg/ml) against an antibioticresistant Enterococcus faecalis isolate, having twice the potency of the compared standard drugs vancomycin and gentamycin sulfate. The compounds also showed moderate antitubercular activity with MIC values between 8 - 128 μg/ml against Mycobacterium tuberculosis and its clinical isolate.

Synthesis and Antimicrobial Evaluation of 2-(p-Substituted Phenyl)-5-[(4-substituted piperazin-1-yl)acetamido]-benzoxazoles

Abstract series of 2-(p-substituted phenyl)-5-(2-{4-[(p-chloro-fluorophenyl)=phenyl] piperazin-1-yl}- acetamido)-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, along with those of previously synthesized analogues, were determined against standard bacterial and fungal strains and drug-resistant isolates, and compared with those of several reference drugs. The new benzoxazole derivatives were found to possess a broad spectrum of antimicrobial activity with MIC values of 32 - 1024 μg/ml. Although the standard drugs were more active against the tested pathogens, the activities of the new benzoxazoles and the reference drugs were largely similar against the drug-resistant isolates.

Synthesis and Antimicrobial Activity of Novel Benzoxazoles

A series of 2-(p-substituted-benzyl)-5-[[4-(p-chloro/fluoro-phenyl)piperazin-1-yl]ace tamido] -benzoxazoles were synthesized in need of new compounds for the fight against microbial pathogens. Their structures were elucidated by spectral techniques. These new derivatives, along with previously synthesized 2-(p-substituted-benzyl)-5-substituted-benzoxazoles, were evaluated for their antibacterial and antifungal activities against standard strains and drugresistant isolates in comparison with ampicillin, gentamicin sulfate, ofloxacin, vancomycin, fluconazole, and amphotericin B trihydrate. The minimum inhibitory concentration (MIC) of each compound was determined by a two-fold serial dilution technique. The compounds were found to possess a broad spectrum of antimicrobial activities with MIC values of 32 - 256 μg/ml. Although standard drugs were more active against the pathogenes employed in this study, the activities of the new benzoxazoles and reference drugs against drug-resistant isolates of the microorganisms were largely similar

Biological evaluation and docking studies of some benzoxazole derivatives as inhibitors of acetylcholinesterase and butyrylcholinesterase

Abstract A series of 2,5-disubstituted-benzoxazole derivatives (1–13) were evaluated as possible inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The results demonstrated that the compounds exhibited a broad spectrum of AChE and BChE inhibitory activity ranging between 6.80% and 90.21% except one compound which showed no activity against AChE at the specified molar concentration. Another derivative displayed a similar activity to that of reference drug (galanthamine) for inhibition of AChE and BChE. In addition, molecular docking of the compounds into active site of AChE was performed using recombinant human AChE (PDB ID: 4ey6) in order to understand ligand–protein interactions.

Abstract 2184: The effects of specific heterocyclic compounds on angiogenesis and apoptosis factors in cancer cells

Introduction: Benzoxazole have received considerable attention during last few decades as they are endowed with variety of biological activities and have wide range of therapeutic properties. The present study aimed to evaluate cytotoxic and antiapoptotic activities of new synthesize benzoxazole derivative in breast cancer cell lines. Material and Method: In this study, the breast cancer cell lines MDA-MB and MCF-7 were used. Cytotoxic activities of novel benzoxazole-derived compound were analyzed with MTT assay. Additionally, the level of its effects on NF-κB and apoptosis-related proteins were examined by the western blot. Immunohistochemical stainings were done for VEGF, eNOS proteins and Tunnel assay was performed to show DNA damage. Results: The structure of the compound synthesized in our study 5-amino-2-(p-bromophenyl)-benzoxazole was proved by elemental analysis, IR, 1H NMR and mass spectroscopy analysis methods. Novel benzoxazole analogue detected cytotoxic on breast cancer cells dose dependent manner, MCF-7 cells were found more sensitive by MTT assay. 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. We observed that it wasn9t between groups in Apaf-1 and BCL-2 levels, but down regulation was observed in caspase 3 and Nfkβ levels compared to control group. Novel benzoxazole compound increased Cytochrome C level in treated cells compared to the control group in MDA-MB cells but not in the MCF-7 cells. Conclusion: In summary, It is felt that this newly synthesized heterocyclic compound increases apoptozis by reducing the activation of Nfkβ, and in this way has shown an effect of inhibiting tumor growth in cancer treatment. Key Words: Heterocyclic Compounds, NF-κB, APAF-1, Cytochrome C, Caspase-3, bcl-2 Citation Format: Funda Kosova, Ozlem Temiz-Arpaci, Ibrahim TUĞLU, Ercument OLMEZ, Feyzan OZDAL KURT, Gorkem KISMALI, Zeki Ari, Mustafa ARISOY. The effects of specific heterocyclic compounds on angiogenesis and apoptosis factors in cancer cells. [abstract]. In: Proceedings of the 107th Annual Meeting of the American Association for Cancer Research; 2016 Apr 16-20; New Orleans, LA. Philadelphia (PA): AACR; Cancer Res 2016;76(14 Suppl):Abstract nr 2184.