Synthesis of 2-Hydroxy-5-(1-(2-(pyrazine-2-carbonyl) hydrazono)hexyl) Benzoic Acid, A Pyrazinamide Analog of Salicylic Acid

  • Glenn V. Alea Department of Chemistry, College of Science, De La Salle University Manila, Malate, Manila
  • Anna Carmina S. Abarquez Department of Chemistry, College of Science, De La Salle University Manila, Malate, Manila
  • Maria Pia Anne B. Austria Department of Chemistry, College of Science, De La Salle University Manila, Malate, Manila
  • Alan Christian S. Lim Department of Chemistry, College of Science, De La Salle University Manila, Malate, Manila
  • Faith Marie G. Lagua Department of Chemistry, College of Science, De La Salle University Manila, Malate, Manila
  • Michael Dominic M. Ajero Department of Chemistry, College of Science, De La Salle University Manila, Malate, Manila
Keywords: tuberculosis, pyrazinamide, salicylic acid, Friedel-Crafts acylation, imine formation

Abstract

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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Published
2013-07-01
How to Cite
Alea, G. V., Abarquez, A. C. S., Austria, M. P. A. B., Lim, A. C. S., Lagua, F. M. G., & Ajero, M. D. M. (2013). Synthesis of 2-Hydroxy-5-(1-(2-(pyrazine-2-carbonyl) hydrazono)hexyl) Benzoic Acid, A Pyrazinamide Analog of Salicylic Acid. KIMIKA, 24(2), 18-26. https://doi.org/10.26534/kimika.v24i2.18-26
Section
Research Articles