Synthesis of 2-hydroxy-5-(1-(2-(pyrazine-2-carbonyl) hydrazono) hexyl) benzoic acid, a pyrazinamide analog of salicylic acid

• Main Authors: Alea, Glenn V., Abarquez, Anna Carmina S., Austria, Michelle Pia B., Lim, Alan Christian S., Lagua, Faith Marie G., Ajero, Michael Dominic M.
• Format: text
• Published: Animo Repository 2013
• Subjects: Pyrazinamide—Synthesis; Mycobacterium tuberculosis; Salicylic acid; Imines; Acylation; Chemistry
• Online Access: https://animorepository.dlsu.edu.ph/faculty_research/7974
• Institution: De La Salle University

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.