RESUMEN
A Smiles-type radical rearrangement induced by visible-light-mediated decarboxylation of ω-aryl- N-(acyloxy)phthalimides was developed, giving rise to pharmacologically important substance classes: phenylethylamine derivatives, dihydroisoquinolinones, and benzoazepinones were synthesized on the basis of readily available benzoic acids or benzaldehydes and ß- or γ-amino acids. This methodology facilitates the synthesis of enantiopure D-amphetamine and of precursors of capsazepinoid bronchodilators.
Asunto(s)
Luz , Procesos Fotoquímicos , Ftalimidas/química , Descarboxilación , EstereoisomerismoRESUMEN
Two new chlorine-containing polyoxygenated seco-cyclohexenes, albanols A (1) and B (2), along with the oxepinone metabolite grandiuvarone (3) were isolated from the endemic Philippine Annonaceae plant Uvaria alba. Both new compounds exhibited modest antitubercular activity. Compound 1 showed cytostatic activity (ranging from 1-50 µM) against HeLa cells and weak antiproliferative activity against HUVEC and K-562 cells with GI50 values of 106 and 81 µM, respectively.
Asunto(s)
Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Cloro/química , Ciclohexenos/química , Ciclohexenos/farmacología , Uvaria/química , Annonaceae/química , Línea Celular , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Células HeLa , Células Endoteliales de la Vena Umbilical Humana , Humanos , Células K562RESUMEN
Chromatographic purification of the DCM sub-extract of Uvaria grandiflora led to the isolation and characterization of a new polyoxygenated cyclohexane derivative, grandifloranol (1), together with five known compounds. Among the compounds isolated, zeylenone (3) showed moderate antitubercular activity against Mycobacterium tuberculosis H37Rv with MIC90 value of 51.2 µM and antiproliferative or cytotoxic activity against human myeloid leukaemia (K-562) and HeLa cells with IC50 values of 2.3 and 18.3 µM, respectively.