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

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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

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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.