Synthesis and nematocide activity of S-glycopyranosyl-6,7-diarylthiolumazines

MARTINS ALHO MIRIAM A; D'ACCORSO NORMA B.; OCHOA CARMEN; CASTRO ANA; CALDERÓN FELIX; CHANA ANTONIO; REVIRIEGO FELIPE; PÁEZ JUAN ANTONIO; CAMPILLO NURIA E.; MARTINEZ-GRUEIRO MERCEDES; LOPEZ-SANTA CRUZ ANA MARÍA; MARTINEZ ANTONIO R

BIOORGANIC & MEDICINAL CHEMISTRY.

Elsevier

Lugar: Amsterdam; Año: 2004 p. 4431 - 4437

0968-0896

Abstract - 6,7-Diaryl derivatives and di-S-glycopyranosylthiolumazine derivatives 5-8 were prepared to test their nematicide activity. In vitro tests against Caenorhabbitis 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 theoritical study on the stability of different possible tautomers of compound 4 was carried out in an attempt to explain some, in appearance, anamalous 13C NMR data of this compound.