@misc{10481/106558,
year = {2025},
month = {9},
url = {https://hdl.handle.net/10481/106558},
abstract = {Herein, a new series of 3-DT analogs with benzoylated groups at C-23 are synthesized
and characterized. The benzoylated groups carry the same substituents in the ortho- or
para-positions. Thus, the effect of structure on activity, measured using the rice lamina
inclination test (RLIT) and the bean second-internode assay (BSI), is evaluated. The RLIT
results indicate that a benzoylate function at C-22 induces a strong increase in activity that
depends on the position and nature of the substituent in the phenyl ring. For example,
an analog with an -OAc group in the ortho-position is the most active derivative, and its
activity is like that of brassinolide. A relative index is calculated using brassinolide as a
positive control to compare the RLIT results with those reported previously. This analysis
allows for the conclusion that benzoylated derivatives with a hydroxyl group at C-3 are
much more active than the corresponding analogs with a carbonyl group in this position,
and one extra alcohol group in the alkyl chain decreases RLIT activity. Finally, the results
obtained with the BSI are clearly different to those obtained in the RLIT bioassay. Therefore,
the application of any activity–structure relationship will always be dependent on the
bioassay used to determine activity.},
organization = {FONDECYT, Fondo Nacional de Desarrollo Científico y
Tecnológico - (grants 1231502 and 3220105)},
publisher = {MDPI},
keywords = {3-dehydroteasterone},
keywords = {brassinosteroid analogs},
keywords = {synthesis},
title = {Novel 3-Dehydroteasterone Derivatives with 23,24-Dinorcholanic Side Chain and Benzoate Groups at C-22: Synthesis and Activity Evaluation by Rice Lamina Inclination Test and Bean Second-Internode Bioassay},
doi = {10.3390/ijms26178710},
author = {Valdés, Ernesto and Díaz, Katy and Núñez, María and Olea, Andrés F. and Quílez Del Moral, José Francisco and Carvajal, Rodrigo and Cuellar, Mauricio and Espinoza Catalán, Luis},
}