Monatshefte für Chemie - Chemical Monthly

, Volume 138, Issue 2, pp 111–119

Synthesis and Structural Studies of 4-Thioxopyrimidines with Antimicrobial Activities

  • Silvio Cunha
  • Rodrigo M. Bastos
  • Priscila de O. Silva
  • Giselle A. Nobre Costa
  • Ivo Vencato
  • Carlito Lariucci
  • Hamilton B. Napolitano
  • Cecília M. A. de Oliveira
  • Lucília Kato
  • Cleuza C. da Silva
  • Diego Menezes
  • Marcos A. Vannier-Santos
Article

DOI: 10.1007/s00706-006-0577-y

Cite this article as:
Cunha, S., Bastos, R., Silva, P. et al. Monatsh. Chem. (2007) 138: 111. doi:10.1007/s00706-006-0577-y

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.

Copyright information

© Springer-Verlag 2007

Authors and Affiliations

  • Silvio Cunha
    • 1
  • Rodrigo M. Bastos
    • 1
  • Priscila de O. Silva
    • 1
  • Giselle A. Nobre Costa
    • 1
  • Ivo Vencato
    • 2
    • 3
  • Carlito Lariucci
    • 2
  • Hamilton B. Napolitano
    • 3
  • Cecília M. A. de Oliveira
    • 4
  • Lucília Kato
    • 4
  • Cleuza C. da Silva
    • 5
  • Diego Menezes
    • 6
  • Marcos A. Vannier-Santos
    • 6
  1. 1.Instituto de QuímicaUniversidade Federal da BahiaCampus de OndinaBrazil
  2. 2.Instituto de FísicaUniversidade Federal de GoiásGoiânia-GOBrazil
  3. 3.Ciências Exatas e Tecnológicas, Universidade Estadual de GoiásAnápolis-GOBrazil
  4. 4.Instituto de QuímicaUniversidade Federal de GoiásGoiânia-GOBrazil
  5. 5.Departamento de QuímicaUniversidade Estadual de MaringáMaringá-PRBrazil
  6. 6.Laboratório de Biomorfologia Parasitária e Microscopia Eletrônica, Centro de Pesquisas Gonçalo MonizFundação Oswaldo Cruz (CPqGM-FIOCRUZ)CandealBrazil