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

AuthorsMartins Alho, Miriam A.; D’Accorso, Norma B.; Ochoa, Carmen; Castro, Ana ; Calderón, Félix ; Chana, Antonio; Reviriego, Felipe ; Páez, Juan A. ; Campillo, Nuria E. ; Martínez-Grueiro, Mercedes; López-Santa Cruz, Ana M.; Martínez, Antonio R.
Issue Date2004
PublisherPergamon Press
CitationBioorganic and Medicinal Chemistry 12: 4431- 4437 (2004)
Abstract6,7-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 13C NMR data of this compound. © 2004 Elsevier Ltd. All rights reserved.
Identifiersdoi: 10.1016/j.bmc.2004.06.004
issn: 0968-0896
e-issn: 1464-3391
Appears in Collections:(IQM) Artículos
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