Structural chemistry and anti-inflammatory activity of flexible/restricted phenyl dimers

Three phenyl dimer compounds, namely 3,3′-Diformyldiphenoxyethane (C16H14O4) (1), 1-(4-[2-(4-Acetyl-phenoxy)-ethoxy]-phenyl)-ethanone (C17H16N2O3) (2), 1-{4-[2-(4-Acetyl-phenoxymethyl)-benzyloxy]-phenyl}-ethanone (C24H22O4) (3), were obtained and fully characterized, including their crystal structure determinations. The structural properties of two compounds 4, 4′-(ethylenedioxy)dibenzaldehyde) (C16H14O4) (Marriott et al. J Med Chem 42:3210, 1999) [1] (4) and 4-(2-Phenoxy-ethoxy)-benzaldehyde (C15H14O3) (Hunter, Chem Soc Rev 23:101, 1994) [2] (5) are discussed with the role of the substituent in crystal packing. In vivo, anti-inflammatory activities of all compounds were studied on Wistar strain albino rats. All the compounds exhibited anti-inflammatory activity except 5. Compounds 1, 2, 4 have shown moderate-to-intermediate effects on inhibitory properties. Compound (3) with restricted rotation in the compound-like SC-558 drug was shown to possess good inhibitory properties at 180 min. In silico analysis was performed and compared with experimental in vivo results.