Synthesis and antifungal activity of C-21 steroids with an aromatic D ring

Juan M Sonego; Adriana M Cirigliano; Gabriela M Cabrera; Gerardo Burton; Adriana S Veleiro

doi:10.1016/j.steroids.2013.02.003

Synthesis and antifungal activity of C-21 steroids with an aromatic D ring

Steroids. 2013 Jul;78(7):644-50. doi: 10.1016/j.steroids.2013.02.003. Epub 2013 Mar 13.

Authors

Juan M Sonego¹, Adriana M Cirigliano, Gabriela M Cabrera, Gerardo Burton, Adriana S Veleiro

Affiliation

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

PMID: 23499954
DOI: 10.1016/j.steroids.2013.02.003

Abstract

Six analogues of salpichrolides with a simplified side chain (6-11) were synthesized using a new methodology to obtain steroids with an aromatic D-ring. The key step was the elimination of HBr in a vicinal dibromo D-homosteroid by treatment with 1,4-diazabicyclo[2.2.2]octane (DABCO). All new compounds were completely characterized by 2D NMR techniques and tested on two fungal pathogenic species, Fusarium virguliforme and Fusarium solani.

Publication types

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

MeSH terms

Antifungal Agents / chemical synthesis*
Antifungal Agents / chemistry
Antifungal Agents / pharmacology*
Ergosterol / chemistry
Fusarium / drug effects
Molecular Structure
Steroids / chemical synthesis*
Steroids / chemistry
Steroids / pharmacology*

Substances

Antifungal Agents
Steroids
Ergosterol