Synthesis and characterization of pyrazinamide analogs of acetylsalicylic acid and salicylic acid
College
College of Science
Department/Unit
Chemistry
Document Type
Article
Source Title
Philippine Journal of Science
Volume
146
Issue
4
First Page
457
Last Page
468
Publication Date
12-1-2017
Abstract
Pyrazinamide (PZA) is one of the first-line of drugs used to treat tuberculosis. It is an important player in shortening the treatment time of the disease from almost a year to only about six months. The occurrence of resistant strains of the bacteria towards PZA threatens its effectiveness in killing semi-dormant and persistent bacilli in the current and future therapy methods to combat the disease. In this study, PZA analogs of salicylic acid (compounds 5a and 5b) and acetylsalicylic acid (compounds 6a and 6b) were synthesized and characterized. The synthesis involved the preparation of salicylic acid and acetylsalicylic acid derivatives with varying acyl chains via Friedel-Crafts acylation of methyl salicylate, followed by subsequent hydrolysis and acetylation to produce the respective precursor compounds. These were then coupled with 2-pyrazinehydrazide to produce the desired PZA analogs. These analogs may exhibit increased potency against PZA-resistant and susceptible strains of Mycobacterium tuberculosis. Characterizations of the compounds were done by IR spectroscopy, high-resolution mass spectrometry, and1H-NMR spectroscopy.
html
Recommended Citation
Alea, G. V., Lagua, F. G., & Ajero, M. M. (2017). Synthesis and characterization of pyrazinamide analogs of acetylsalicylic acid and salicylic acid. Philippine Journal of Science, 146 (4), 457-468. Retrieved from https://animorepository.dlsu.edu.ph/faculty_research/1979
Disciplines
Chemistry
Keywords
Pyrazinamide; Salicylic acid; Tuberculosis; Aspirin; Friedel-Crafts reaction
Upload File
wf_no