Article

Monatshefte für Chemie - Chemical Monthly

, Volume 138, Issue 2, pp 111-119

Synthesis and Structural Studies of 4-Thioxopyrimidines with Antimicrobial Activities

  • Silvio CunhaAffiliated withInstituto de Química, Universidade Federal da Bahia Email author 
  • , Rodrigo M. BastosAffiliated withInstituto de Química, Universidade Federal da Bahia
  • , Priscila de O. SilvaAffiliated withInstituto de Química, Universidade Federal da Bahia
  • , Giselle A. Nobre CostaAffiliated withInstituto de Química, Universidade Federal da Bahia
  • , Ivo VencatoAffiliated withInstituto de Física, Universidade Federal de GoiásCiências Exatas e Tecnológicas, Universidade Estadual de Goiás
  • , Carlito LariucciAffiliated withInstituto de Física, Universidade Federal de Goiás
  • , Hamilton B. NapolitanoAffiliated withCiências Exatas e Tecnológicas, Universidade Estadual de Goiás
  • , Cecília M. A. de OliveiraAffiliated withInstituto de Química, Universidade Federal de Goiás
  • , Lucília KatoAffiliated withInstituto de Química, Universidade Federal de Goiás
    • , Cleuza C. da SilvaAffiliated withDepartamento de Química, Universidade Estadual de Maringá
    • , Diego MenezesAffiliated withLaboratório de Biomorfologia Parasitária e Microscopia Eletrônica, Centro de Pesquisas Gonçalo Moniz, Fundação Oswaldo Cruz (CPqGM-FIOCRUZ)
    • , Marcos A. Vannier-SantosAffiliated withLaboratório de Biomorfologia Parasitária e Microscopia Eletrônica, Centro de Pesquisas Gonçalo Moniz, Fundação Oswaldo Cruz (CPqGM-FIOCRUZ)

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Summary.

This work describes a two-step, one-pot synthetic method for the formal aza-[3 + 3] cycloaddition between N-alkyl substituted enaminones and benzoyl isothiocyanate, which afforded 4-thioxopyrimidines in reasonable yields. Reaction of acyclic enaminone with a sterically hindered group attached to the nitrogen atom afforded pyridine-2-thione, yet in low yield. The antibacterial, antifungal, and trypanocidal activities of the thioxopyrimidines were evaluated and five compounds exhibited moderate activity against Candida albicans, Micrococcus luteus, and Trypanosoma cruzi. The solid state structures of a thioxopyrimidine, an organic disulfide, and a 1,2,4-triazole were determined by X-ray diffraction analysis.

Keywords. Cyclizations; Enaminones; Heterocycles; Pyrimidine-4-thiones; X-ray structure determination.