Synthesis of pyrazinamide analogs of aspirin

Authors

Glenn V. Alea, De La Salle University, Manila
Faith Marie G. Lagua, De La Salle University, Manila
Michael Dominic M. Ajero, De La Salle University, Manila

College

College of Science

Department/Unit

Chemistry

Document Type

Conference Proceeding

Source Title

DLSU Research Congress 2012

First Page

112-1

Last Page

112-5

Publication Date

2012

Abstract

Pyrazinamide derivatives of aspirin (6a) and (6b) were synthesized. The synthesis involved teh Friedel Crafts acylation of methyl salicylate using the appropriate alkanoyl chloride and ZnCl₂ as catalyst followed by hydrolysis to produce the precursor compounds (3a) and (3b). Compound (3a) was coupled with the pyrazinamide moiety via imine formation followed by acetylation to produce compound (6a) in 41.10% yield. Compound (6b) was generated in 8.207% yield from the coupling of acetylated compound (3b) and 2-pyrazinehydrazide. These compounds may exhibit improved activity against pyrazinamide resistant and susceptible strains of Mycobacterium tuberculosis. A recent study has shown that the activity of pyrazinamide is enhanced if administered together with aspirin.

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Recommended Citation

Alea, G. V., Lagua, F. G., & Ajero, M. M. (2012). Synthesis of pyrazinamide analogs of aspirin. DLSU Research Congress 2012, 112-1-112-5. Retrieved from https://animorepository.dlsu.edu.ph/faculty_research/7784

Disciplines

Chemistry

Keywords

Pyrazinamide—Synthesis; Mycobacterium tuberculosis

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