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

Kinetic study of the cobalt electrodeposition onto glassy carbon electrode from ammonium sulfate sol...

Efecto de la composición del soporte sobre las estructuras superficiales de óxidos de níquel y molib...

The role of temperature in copper electrocrystallization in ammoniachloride solutions

Influence of the Cation Nature of the Sulphate Salt on the Electrochemical Synthesis of Sulfate-Dope...

Chemical Reactivity of Atrazine Employing the Fukui Function

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

Electrochemical kinetic study about cobalt electrodeposition onto GCE and HOPG substrates from sulfa...

Cobalt electrodeposition on polycrystalline palladium. Influence of temperature on kinetic parameter...

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

Revisión de variables de diseño y condiciones de operación en la electrocoagulación