Synthesis and nematocide activity of S-glycopyranosyl-6,7-diarylthiolumazines.
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.
Martins Alho
Miriam A
MA
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.
D'Accorso
Norma B
NB
Ochoa
Carmen
C
Castro
Ana
A
Calderón
Félix
F
Chana
Antonio
A
Reviriego
Felipe
F
Páez
Juan Antonio
JA
Campillo
Nuria E
NE
Martínez-Grueiro
Mercedes
M
López-Santa Cruz
Ana María
AM
Martínez
Antonio R
AR
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*
D000969:Antinematodal Agents; D006027:Glycosides; D011621:Pteridines