3-Deoxy-D-erythro-hexos-2-ulose bis(thiosemicarbazone) (1) acts as a tetradentate ligand of the N2S2 type which forms stable coordination complexes with metal(II) cations. The Cu(II), Pt(II), and Pd(II) chelates (2, 4, and 6, respectively) of 1 were synthesized and characterized by elemental analysis and NMR spectroscopy. The NMR spectra of the Pt complex (4) showed the coupling of H-1 and C-1, C-2 of the bis(thiosemicarbazone) with 195Pt (33.7% naturally occurring), which supports the structure proposed for the chelate. The complexes 2, 4, and 6 were acetylated to give the corresponding tri-O-acetyl derivatives 3, 5, and 7. Elimination of Cu(II) from 3 with hydrogen sulfide afforded 8, the tri-O-acetyl derivative of 1. Preliminary studies have shown antiviral activity of chelates 2, 4, and 6 against poliovirus type 1. (C) 2000 Elsevier Science Ltd.
Documento: | Artículo |
Título: | Cu, Pt, and Pd complexes of the 3-deoxy-1,2-bis(thiosemicarbazone) derived from D-glucose |
Autor: | Horton, D.; Varela, O. |
Filiación: | Department of Chemistry, Amer. Univ., 4400 Massachusetts A., Washington, DC 20016-8014, United States CIHIDECAR (CONICET)-Depto. Quim. O., Fac. Cie. Exact. Y Nat., Univ. B., Buenos Aires, Argentina |
Palabras clave: | Bis(thiosemicarbazone); Chelates; Copper; Palladium; Platinum; 3 deoxy dextro erythro hexos 2 ulose bis(thiosemicarbazone) palladium chelate; 3 deoxy dextro erythro hexos 2 ulose bis(thiosemicarbazone) platinum chelate; acetic acid derivative; chelate; copper; glucose; hydrogen sulfide; metal ion; palladium complex; platinum; thiosemicarbazone derivative; unclassified drug; antiviral activity; article; complex formation; nuclear magnetic resonance spectroscopy; Poliomyelitis virus 1; priority journal; Animal; Antiviral Agents; Cercopithecus aethiops; Copper; Glucose; Human; Magnetic Resonance Spectroscopy; Palladium; Platinum Compounds; Poliovirus; Thiosemicarbazones; Vero Cells |
Año: | 2000 |
Volumen: | 328 |
Número: | 3 |
Página de inicio: | 425 |
Página de fin: | 429 |
DOI: | http://dx.doi.org/10.1016/S0008-6215(00)00118-X |
Título revista: | Carbohydrate Research |
Título revista abreviado: | Carbohydr. Res. |
ISSN: | 00086215 |
CODEN: | CRBRA |
CAS: | copper, 15158-11-9, 7440-50-8; glucose, 50-99-7, 84778-64-3; hydrogen sulfide, 15035-72-0, 7783-06-4; platinum, 7440-06-4; Antiviral Agents; Copper, 7440-50-8; Glucose, 50-99-7; Palladium, 7440-05-3; Platinum Compounds; Thiosemicarbazones |
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v328_n3_p425_Horton |