Synthesis of pyrazinamide analogs of aspirin
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 couple...
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| Main Authors: | , , |
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| Format: | text |
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Animo Repository
2012
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| Subjects: | |
| Online Access: | https://animorepository.dlsu.edu.ph/faculty_research/7784 |
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| Institution: | De La Salle University |
| Summary: | 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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