Producción Científica Profesorado

Uncommon Reactivity of a Seco-Oxacassane Diterpenoid and Antiproliferative Activity of Some Derivatives



Mendoza Huizar, Luis Humberto

2021

Alexia Hernández-Jiménez, Ledy De-la-Cruz-Martínez, Raúl Velasco-Azorsa, Reyna Zeferino-Díaz, José G. Alvarado-Rodríguez, Luis H. Mendoza-Huizar, J. Jesús Manríquez-Torres, Horacio Almanza-Reyes, Carlos M. Cerda-Garcia-Rojas, Pedro Joseph-Nathan, and J. Martín Torres-Valencia. Uncommon Reactivity of a Seco-Oxacassane Diterpenoid and Antiproliferative Activity of Some Derivatives, .Heterocycles, 2021, 102(7), pp. 1301?1313. DOI: 10.3987/COM-21-14432


Abstract


The main diterpenoid of Acacia schaffneri, 7,8-seco-7,8-oxacassa-13,15-dien-7-ol-17-al (1), has two aldehydes of which one is protected as a ?-lactol. The free aldehyde resisted to afford the carboxylic acid using reagents with different oxidative strength, although 1 gave oxime 2 when treated with hydroxylamine, ?-hydroxyketone 3 after addition of acetone, aldo-?-lactone 4 whereby only the lactol was oxidized when using Jones reagent, and epoxyformate 5 after Baeyer-Villiger treatment. Hydrolysis of 5 with NaHCO3 gave 6. Structures 2?6 followed from physical and spectral data including X-ray diffraction. All compounds showed antiproliferative activity similar to some chemotherapeutic drugs against C2C12, L929, SiHa, and MDA-MB-231 cell lines.






Artículos relacionados

A Semiempirical PM6 Study of Some Aminopyrimidine Derivatives and their Interaction with an Iron Sur...

Bioacumulación y daños genotóxicos en Pez Cebra (Danio rerio) por arsénico en aguas de Zimapán, Hida...

Cobalt electrodeposition onto highly oriented pyrolytic graphite (HOPG) electrode from ammonium sulf...

Estudio de las Interacciones Ácido Húmico-Metales Pesados y Determinación de sus Constantes de Estab...

Synthesis and crystal structures of cis-palladium(II) and cis-platinum(II) complexes containing di...

ELECTROCHEMICAL STUDY ABOUT ZINC ELECTRODEPOSITION ONTO GCE AND HOPG SUBSTRATES

The role of temperature in copper electrocrystallization in ammoniachloride solutions

Characterization of Main Anthocyanins Extracted from Pericarp Blue Corn by MALDI-ToF MS

Chemical Reactivity of Atrazine Employing the Fukui Function

Quantum chemical study of the electrochemical reduction of the [Co(H2O)6]2+ and [Co(NH3)5(H2O)]2+ io...