| Autor: |
Sartillo-Piscil F; Centro de Investigación de la Facultad de Ciencias Químicas, BUAP (Benemérita Universidad Autónoma de Puebla) , 14 Sur Esq. San Claudio, San Manuel, 72570 Puebla, Mexico., Quintero L, Cruz-Gregorio S, Espinosa-Aguirre J, Elinos-Baez CM, Höpfl H, Serrano A |
| Jazyk: |
angličtina |
| Zdroj: |
The Journal of organic chemistry [J Org Chem] 2014 Oct 17; Vol. 79 (20), pp. 9647-54. Date of Electronic Publication: 2014 Oct 03. |
| DOI: |
10.1021/jo501772g |
| Abstrakt: |
On the basis of previous conformational and configurational studies of 4-aryl-substituted cyclophosph(on)ates derived from d-xylofuranose derivatives, wherein it was proposed that the anomeric effect is involved in the spontaneous isomerization of the P atom and the C4 carbon, and consequently, this unusual behavior was associated with the cleavage of the HepDirect prodrugs. We synthesized an analogous series of 2-amino-2-oxo-1,3,2-dioxaphosphorinanes and performed a conformational and configurational analysis in solution and the solid state followed by an examination of their mutagenic activity. The results showed that the 2-amino-2-oxo-1,3,2-dioxaphosphorinanes with the largest mutagenic activity contain either a 4-methoxyphenyl or 4-fluorophenyl group at C4 carbon and presented a major chair conformation, which is prone to weaken the C4-O3 bond via the anomeric effect and facilitates the cleavage for the release of the biologically active metabolite. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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