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Reactions of CF 3 -enones with arenes under superelectrophilic activation: a pathway to trans-1,3-diaryl-1-CF 3 -indanes, new cannabinoid receptor ligands
4-Aryl-1,1,1-trifluorobut-3-en-2-ones ArCHCHCOCF 3 (CF 3 -enones) react with arenes in excess of Brønsted superacids (TfOH, FSO 3 H) to give, stereoselectively, trans -1,3-diaryl-1-trifluoromethyl indanes in 35–85% yields. The reaction intermediates, the O-protonated ArCHCHC(OH + )CF 3 and the O,C-diprotonated ArHC + CH 2 C(OH + )CF 3 species, have been studied by means of 1 H, 13 C, 19 F NMR, and DFT calculations. Both types of the cations may participate in the reaction, depending on their electrophilicity and electron-donating properties of the arenes. The formation of CF 3 -indanes is a result of cascade reaction of protonated CF 3 -enones to form chemo-, regio- and stereoselectively three new C–C bonds. The obtained trans -1,3-diaryl-1-trifluoromethyl indanes were investigated as potential ligands for cannabinoid receptors CB 1 and CB 2 types. The most potent compound showed sub-micromolar affinity for both receptor subtypes with a 6-fold selectivity toward the CB 2 receptor with no appreciable cytotoxicity toward SHSY5Y cells.
Sprache
Englisch
Identifikatoren
ISSN: 1477-0520
eISSN: 1477-0539
DOI: 10.1039/C5OB01072A
Titel-ID: cdi_crossref_primary_10_1039_C5OB01072A
Format
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