Synthesis of 2-hydroxy-5-(1-(2-(pyrazine-2-carbonyl) hydrazono) hexyl) benzoic acid, a pyrazinamide analog of salicylic acid
The occurrence of resistant strains of Mycobacterium tuberculosis has driven current research on combining current anti-tuberculosis drugs and other bioactive molecules to enhance their efficacy against susceptible and resistant strains of the bacteria. In this study, a salicylic acid derivative of...
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| Main Authors: | , , , , , |
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| Format: | text |
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Animo Repository
2013
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| Subjects: | |
| Online Access: | https://animorepository.dlsu.edu.ph/faculty_research/7974 |
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| Institution: | De La Salle University |
| Summary: | The occurrence of resistant strains of Mycobacterium tuberculosis has driven current research on combining current anti-tuberculosis drugs and other bioactive molecules to enhance their efficacy against susceptible and resistant strains of the bacteria. In this study, a salicylic acid derivative of pyrazinamide, 2-hydroxy-5-(1-(2-(pyrazine-2-carbonyl) hydrazono) hexyl) benzoic acid was synthesized and characterized. The compound was prepared by coupling a pyrazinamide moiety, one of the first line drugs used to treat tuberculosis and a salicylic acid derivative with a 6-carbon alkyl chain. The salicylic acid derivative was generated via Friedel-Crafts acylation of methyl salicylate followed by base hydrolysis of the acylated product. This was coupled with the pyrazinamide moiety via imine formation. The product, 2-hydroxy-5-(1-(2-(pyrazine-2-carbonyl) hydrazono) hexyl) benzoic acid was obtained as an off-white powder in 62% yield. |
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