Synthesis of 1,3,4-oxadiazoles with 4-methoxynaphthalene ring: discovering new compounds with antimicrobial activity

Future Med Chem. 2023 Dec;15(24):2239-2255. doi: 10.4155/fmc-2023-0153. Epub 2023 Nov 28.

Abstract

Background: Paracoccidioidomycosis (PCM) is a systemic infection caused by Paracoccidioides spp. (Pb). PCM can be associated or clinically confused with tuberculosis (TB), another pulmonary infection, caused by Mycobacterium tuberculosis (Mtb). Futhermore, the long treatment time of TB and PCM and the cases of TB drug resistance impose difficulties for the cure of these diseases. Results: New 1,3,4-oxadiazoles containing the 4-methoxynaphthalene ring were synthesized and their antimicrobial activity was evaluated against Pb and Mtb. The derivative 6n (with 2-hydroxy-5-nitrophenyl subunit) is the most promising of the series. Conclusion: The 1,3,4-oxadiazole 6n can be used as a prototype drug candidate, with anti-Pb and anti-MTb activities, showing a broad-spectrum profile for the treatment of both pulmonary infections.

Keywords: 1-3-4-oxadiazoles; 4-methoxynaphthalene; co-infection; paracoccidioidomycosis; tuberculosis.

MeSH terms

  • Anti-Infective Agents* / pharmacology
  • Anti-Infective Agents* / therapeutic use
  • Humans
  • Lead / therapeutic use
  • Mycobacterium tuberculosis*
  • Oxadiazoles / pharmacology
  • Paracoccidioidomycosis* / drug therapy
  • Paracoccidioidomycosis* / microbiology
  • Tuberculosis* / drug therapy

Substances

  • Oxadiazoles
  • Lead
  • Anti-Infective Agents