Novel tetracyclic structures from the synthesis of thiolactone-isatin hybrids

• Renate Hazel Hans,
• Hong Su and
• Kelly Chibale

Beilstein J. Org. Chem. 2010, 6, No. 78, doi:10.3762/bjoc.6.78

• 7701, South Africa 10.3762/bjoc.6.78 Abstract A simple and straightforward synthetic approach to potential anti-infective thiolactone-isatin hybrids led to the discovery of novel tetracyclic compounds which bear a macrocylic motif containing an unusual bridged amide bond. Keywords: bridged amides

• affects their reactivity and stability [26][27][28][29][30][31]. Furthermore, the use of bridged amides as scaffolds in medicinal chemistry has been explored [32][33][34][35][36][37]. Indeed, the enhanced electrophilicity or acylating ability of β-lactams is partially attributed to the distortion from

• 4a, the indole moiety is nearly planar with the maximum deviation from the least-squares plane for all the nine atoms in the ring at +0.045(1) and +0.0412(15) for C8, in 4b and 4c, respectively. In recognition of the potential contribution of distorted bridged amides to biological activity as alluded