Syntheses of 2-Hydroxy-4,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one: A precursor of a bioactive electrophile from Gramineae

Carlos A. Escobar, Michael Kluge, Dieter Sicker

Resultado de la investigación: Article

9 Citas (Scopus)

Resumen

2-Hydroxy-4,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one (8), the hitherto undescribed free hemiacetatic aglycone of a benzoxazinoid acetal glucoside naturally occurring in wheat, has been synthesized following two pathways, independently. This cyclic hydroxamic acid methyl ester proved to be very unstable when in solution. This gives rise to the assumption that HDIBOA naturally released from its acetal glucoside is by methoxide elimination a precursor to form a multi-centered electrophile that was recently reported to be the bioactive principle of the benzoxazinoid lead.

Idioma originalEnglish
Páginas (desde-hasta)1017-1020
Número de páginas4
PublicaciónTetrahedron Letters
Volumen38
N.º6
DOI
EstadoPublished - 10 feb 1997

Huella dactilar

Benzoxazines
Acetals
Glucosides
Poaceae
Hydroxamic Acids
Triticum
Esters

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Citar esto

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abstract = "2-Hydroxy-4,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one (8), the hitherto undescribed free hemiacetatic aglycone of a benzoxazinoid acetal glucoside naturally occurring in wheat, has been synthesized following two pathways, independently. This cyclic hydroxamic acid methyl ester proved to be very unstable when in solution. This gives rise to the assumption that HDIBOA naturally released from its acetal glucoside is by methoxide elimination a precursor to form a multi-centered electrophile that was recently reported to be the bioactive principle of the benzoxazinoid lead.",
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Syntheses of 2-Hydroxy-4,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one : A precursor of a bioactive electrophile from Gramineae. / Escobar, Carlos A.; Kluge, Michael; Sicker, Dieter.

En: Tetrahedron Letters, Vol. 38, N.º 6, 10.02.1997, p. 1017-1020.

Resultado de la investigación: Article

TY - JOUR

T1 - Syntheses of 2-Hydroxy-4,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one

T2 - A precursor of a bioactive electrophile from Gramineae

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AU - Kluge, Michael

AU - Sicker, Dieter

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