Uncommon Reactivity of a Seco-Oxacassane Diterpenoid and Antiproliferative Activity of Some Derivatives
Alvarado Rodríguez, José Guadalupe
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.