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

• Published in: Steroids Vol. 78; no. 7; pp. 644 - 650
• Main Authors: Sonego, Juan M., Cirigliano, Adriana M., Cabrera, Gabriela M., Burton, Gerardo, Veleiro, Adriana S.
• Format: Journal Article
• Language: English
• Published: United States Elsevier Inc 01-07-2013
• Subjects: Antifungal activity; Antifungal Agents - chemical synthesis; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; Aromatic D-ring; DABCO; Ergosterol - chemistry; Fusarium - drug effects; Molecular Structure; Salpichrolides; Steroids - chemical synthesis; Steroids - chemistry; Steroids - pharmacology; Antifungal activity; Salpichrolides; DABCO; Aromatic D-ring
• ISSN: 0039-128X; 1878-5867
• DOI: 10.1016/j.steroids.2013.02.003

► A simple methodology for the preparation of steroids with an aromatic D ring was developed. ► Six analogues of salpichrolides with an aromatic D ring and a simplified side chain were synthesized. ► The antifungal activity was evaluated on two fungal pathogenic species: Fusarium virguliforme and Fusarium solani. ► Two analogues had activity comparable to the natural salpichrolides.
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.