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Substitution of a sulfonamide for an amide linker has detrimental effects on the capability of 7 to bind to PPARγ. Shown is a superimposition of the 7 structure (white) with the 1 structure (green). The carbon of the C=O in 7 (white sticks) is confined to a planar conformation which prevents the A ring of 7 from making favorable π–π interactions with Phe363 as well as hydrophobic interactions with residues of the binding pocket.
