Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 15, Issue 38, Pages 8218-8231Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ob01917c
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Funding
- Cost Association STREAM [FA1206]
- Compagnia di San Paolo Foundation
- CRT Foundation/ISI
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In this paper, we synthesized and evaluated the biological activity of structural analogues of natural strigo-lactones in which the butenolide D-ring has been replaced with a gamma-lactam. The key step to obtain the alpha, beta-unsaturated-gamma-lactam was an RCM on suitably substituted amides. Strigolactones (SLs) are plant hormones with various developmental functions. As soil signaling chemicals, they are required for establishing beneficial mycorrhizal plant/fungus symbiosis. Beside these auxinic roles, recently SLs have been successfully investigated as antitumoral agents. Peculiar to the SL perception system is the enzymatic activity of the hormone receptor. SARs data have shown that the presence of the butenolide D-ring is crucial to retain the biological activity. The substitution of the butenolide with a lactam might shed light on the mechanism of perception. In the following, a dedicated in silico study suggested the binding modes of the synthesized compounds to the receptor of SLs in plants.
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