Author(s):
Cunha, Silvio do Desterro ; Bastos, Rodrigo M. ; Silva, Priscila de O. ; Costa, Giselle A. Nobre ; Vencato, Ivo ; Lariucci, Carlito ; Napolitano, Hamilton B. ; Oliveira, Cecília M. A. de ; Kato, Lucília ; Silva, Cleuza C. da ; Menezes, Diego ; Santos, Marcos André Vannier dos ; Cunha, Silvio do Desterro ; Bastos, Rodrigo M. ; Silva, Priscila de O. ; Costa, Giselle A. Nobre ; Vencato, Ivo ; Lariucci, Carlito ; Napolitano, Hamilton B. ; Oliveira, Cecília M. A. de ; Kato, Lucília ; Silva, Cleuza C. da ; Menezes, Diego ; Santos, Marcos André Vannier dos
Date: 2014
Origin: Oasisbr
Subject(s): Cyclizations; Enaminones; Heterocycles; Pyrimidine-4-thiones; X-ray structure determination
Description
Texto completo: acesso restrito. p.111-119
Submitted by Suelen Reis (suziy.ellen@gmail.com) on 2014-03-12T12:00:37Z No. of bitstreams: 1 art%3A10.1007%2Fs00706-006-0577-y.pdf: 336694 bytes, checksum: 95e7287cb3a43f33fd40c9fbef11ab45 (MD5)
Made available in DSpace on 2014-03-12T12:00:37Z (GMT). No. of bitstreams: 1 art%3A10.1007%2Fs00706-006-0577-y.pdf: 336694 bytes, checksum: 95e7287cb3a43f33fd40c9fbef11ab45 (MD5) Previous issue date: 2007
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.
