title: Synthesis and nematocide activity of S-glycopyranosyl-6,7-diarylthiolumazines.
abstract: 6,7-Diaryl derivatives of mono and di-S-glycopyranosylthiolumazine derivatives 5-8 were prepared to test their nematocide activity. In vitro tests against Caenorhabditis elegans were performed and it was found that monosubstituted derivatives 5-7 showed higher activity than the corresponding unsubstituted 2-thiolumazines 1-3, whilst 2-S,4-S-di-glycopyranosylpteridine derivative 8 was inactive in contrast to unsubstituted derivative 4. In order to check whether the lack of activity of 8 was due to the two bulky substituents of the pteridine nucleus, 2-S,4-S-dimethyl derivative 9 was synthesized and assayed showing also lack of activity. A theoretical study on the stability of the different possible tautomers of compound 4 was carried out in an attempt to explain some, in appearance, anomalous (13)C NMR data of this compound.
authors.affiliation: Centro de Investigaciones en Hidratos de Carbono, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina.
authors.forename: Miriam A
authors.initials: MA
authors.lastname: Martins Alho
authors.forename: Norma B
authors.initials: NB
authors.lastname: D'Accorso
authors.forename: Carmen
authors.initials: C
authors.lastname: Ochoa
authors.forename: Ana
authors.initials: A
authors.lastname: Castro
authors.forename: Félix
authors.initials: F
authors.lastname: Calderón
authors.forename: Antonio
authors.initials: A
authors.lastname: Chana
authors.forename: Felipe
authors.initials: F
authors.lastname: Reviriego
authors.forename: Juan Antonio
authors.initials: JA
authors.lastname: Páez
authors.forename: Nuria E
authors.initials: NE
authors.lastname: Campillo
authors.forename: Mercedes
authors.initials: M
authors.lastname: Martínez-Grueiro
authors.forename: Ana María
authors.initials: AM
authors.lastname: López-Santa Cruz
authors.forename: Antonio R
authors.initials: AR
authors.lastname: Martínez
mesh_terms: D000818:Animals; D000969:Antinematodal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D017173:Caenorhabditis elegans / Q000187:drug effects; D006027:Glycosides / Q000138:chemical synthesis* / Q000494:pharmacology*; D011621:Pteridines / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D000969:Antinematodal Agents; D006027:Glycosides; D011621:Pteridines