STRUCTURE-ACTIVITY-RELATIONSHIPS OF SOME ANTIMICROBIAL 5-SUBSTITUTED 2-(3-PYRIDYL) BENZOXAZOLES USING QUANTUM-CHEMICAL CALCULATIONS

Date

1994-09-19

Author

SENER, E
TURGUT, H
YALCIN, I
OREN, I
Türker, Burhan Lemi
CELEBI, N
AKIN, A

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

166
views

0
downloads

The synthesis and in vitro antimicrobial activity of 5-substituted 2-(3-pyridyl)benzoxazoles (3-7) is described for some Gram-positive and Gram-negative bacteria and the yeast Candida albicans. The compounds 3-7 exhibited significant activity against the screened microorganisms, having MIC values between 25 and 12.5 mu g/ml. Quantum-chemical calculations were performed for the compounds 1-10, in order to observe some feasible structure-activity relationships. These theoretical observations, calculated for the description of the mechanism of interactions at the molecular level, revealed that the electrophilic superdelocalizability of the nitrogen atom (S-N(E)) in the oxazolo moiety of the benzoxazole ring is related to the activity. The results obtained from the theoretical calculations and the observed MIC values shaw that 2-(3-pyridyl)- and 2-phenylbenzoxazole derivatives exhibit bio-isosteric effects for antimicrobial activity. Additionally, substituents at position 5 on the fused heterocyclic system contribute to the activity constructively or destructively depending on the type of microorganism screened.

Subject Keywords

Pharmaceutical Science

URI

https://hdl.handle.net/11511/63022

Journal

INTERNATIONAL JOURNAL OF PHARMACEUTICS

DOI

https://doi.org/10.1016/0378-5173(94)90148-1

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

SYNTHESIS AND ANTIFUNGAL ACTIVITY OF SOME NEW BENZIMIDAZOLE DERIVATIVES GOKER, H; ERTAN, R; AKGUN, H; YULUG, N (Wiley, 1991-05-01) Synthesis and antifungal evaluation of 5-ethoxycarbonyl-2-(substituted-benzyl or phenoxymethyl)benzimidazoles are reported. Structures of the compounds were elucidated with IR-, H-1-NMR-, C-13-NMR-, mass-spectra and elemental analysis. Preliminary results show that none of the synthesized benzimidazole derivatives has antifungal activity at the concentration of 100-mu-g/ml against Candida parapsilosis, Candida stellatoidea, and Candida pseudotropicalis.
A NONIONIC SURFACTANT VESICLE-IN-WATER-IN-OIL (V/W/O) SYSTEM - POTENTIAL USES IN DRUG AND VACCINE DELIVERY YOSHIOKA, T; SKALKO, N; Gürsel, Mayda; GREGORIADIS, G; FLORENCE, AT (Informa UK Limited, 1995-01-01) An aqueous dispersion of niosomes (non-ionic surfactant vesicles) emulsified in an external oil phase forms the vesicle-in-water-in-oil (v/w/o) system described in this paper. The properties of the surfactant used to form the vesicles, the surfactant or surfactant mixture used to stabilize the emulsion and the nature of the oil phase can be changed to provide systems of different capacities for drug or antigen and different release characteristics. The same nonionic surfactant is used as the principle amphi...
Concentration-dependent differing actions of the nonsteroidal anti-inflammatory drug, celecoxib, in distearoyl phosphatidylcholine multilamellar vesicles Sade, Asli; Banerjee, Sreeparna; Severcan, Feride (Informa UK Limited, 2010-06-01) The interactions of the nonsteroidal anti-inflammatory drug, celecoxib, with 1,2-distearoyl-sn-glycero-3-phosphocholine multilamellar vesicles were studied as a function of temperature and different drug concentrations, using Fourier transform infrared spectroscopy, differential scanning calorimetry, and turbidity technique at 440 nm. Our studies reveal that celecoxib lowers the main phase-transition temperature and decreases the fluidity of the membranes at all concentrations. Celecoxib induced opposing ef...
Preparation and characterization of cyclodextrin nanosponges for organic toxic molecule removal VARAN, CEM; Anceschi, Anastasia; Sevli, Serhat; Bruni, Natascia; Giraudo, Leonardo; BİLGİÇ, ELİF; KORKUSUZ, PETEK; Iskit, Alper B.; Trotta, Francesco; BİLENSOY, EREM (Elsevier BV, 2020-07-01) Cyclodextrin-based nanosponges (CD-NS) are considered as safe and biocompatible systems for removing toxic molecules from the body. Rapid removal of toxic molecules that are formed in the body from certain food constituents, is relevant especially for patients affected by chronic kidney disease. Within the scope of this study, innovative cyclodextrin polymers were synthesized to form nanosponges able to remove indole, before it could form the toxic indoxyl sulfate in the body. Furthermore, in vivo studies w...
Encapsulation of two different TLR ligands into liposomes confer protective immunity and prevent tumor development Bayyurt, Banu; Tincer, Gizem; Almacioglu, Kubra; Alpdundar, Esin; Gürsel, Mayda; GÜRSEL, İHSAN (Elsevier BV, 2017-02-10) Nucleic acid-based Toll-like receptor (TLR) ligands are promising adjuvants and immunotherapeutic agents. Combination of TLR ligands potentiates immune response by providing synergistic immune activity via triggering different signaling pathways and may impact antigen dependent T-cell immune memory. However, their short circulation time due to nuclease attack hampers their clinical performance. Liposomes offer inclusion of protein and nucleic acid-based drugs with high encapsulation efficiency and drug load...

Citation Formats

E. SENER et al., “STRUCTURE-ACTIVITY-RELATIONSHIPS OF SOME ANTIMICROBIAL 5-SUBSTITUTED 2-(3-PYRIDYL) BENZOXAZOLES USING QUANTUM-CHEMICAL CALCULATIONS,” INTERNATIONAL JOURNAL OF PHARMACEUTICS, pp. 109–115, 1994, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/63022.