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

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

Nucleation and Growth Kinetics of Electrodeposited Sulfate-Doped Polypyrrole: Determination of the D...

Cobalt Electrodeposition Process from Electrolytic Baths based on CoSO4 and (NH4)2SO4. Influence of ...

Do Spiroarsoranes Exhibit Polytopal Equilibrium in Solution?

Nucleation and growth of cobalt onto different substrates: Part II. The upd-opd transition onto a go...

Predicting the Phase Diagram of a Liquid Crystal Using the Convex Peg Model and the Semiempirical PM...

Nucleation and growth of cobalt onto different substrates: Part I. Underpotential deposition onto a ...

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

Kinetics of Polypyrrole Films Doped with Sulphate Ions Electrodeposited Over Graphite - Epoxy Resin ...

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