Synthesis and biological activity of brassinosteroids fluorinated at C-2

Sofía L Acebedo; Javier A Ramírez; Lydia R Galagovsky

doi:10.1016/j.steroids.2008.12.006

Synthesis and biological activity of brassinosteroids fluorinated at C-2

Steroids. 2009 Apr-May;74(4-5):435-40. doi: 10.1016/j.steroids.2008.12.006. Epub 2008 Dec 30.

Authors

Sofía L Acebedo¹, Javier A Ramírez, Lydia R Galagovsky

Affiliation

¹ Departamento de Química Orgánica and UMYMFOR (CONICET - Facultad de Ciencias Exactas y Naturales), Universidad de Buenos Aires, Pabellón 2, Piso 3, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina.

PMID: 19150620
DOI: 10.1016/j.steroids.2008.12.006

Abstract

In this paper we report the synthesis of four fluorinated analogues of brassinosteroids in which fluorine was introduced stereoselectively at C-2. The bioactivity of these new compounds was evaluated using the rice lamina inclination test. The results show that two of these analogues elicit high bioactivity, suggesting the involvement of hydrogen bond interactions between the active brassinosteroids and their cellular receptor.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Biological Assay
Brassinosteroids
Cholestanols / chemical synthesis*
Cholestanols / chemistry
Cholestanols / pharmacology*
Halogenation / drug effects*
Oryza / drug effects
Steroids, Heterocyclic / chemical synthesis*
Steroids, Heterocyclic / chemistry
Steroids, Heterocyclic / pharmacology*

Substances

Brassinosteroids
Cholestanols
Steroids, Heterocyclic
brassinolide