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

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Abstract

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.

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Acknowledgements

Department of Chemistry, Banaras Hindu University, Varanasi, India, is acknowledged for departmental facilities. Department of Chemistry, Mizoram University, Aizawl, Mizoram, India, is acknowledged the other infrastructure facilities. SAIF, Gauhati University, Guwahati, India, is acknowledged for SCXRD facilities. Institute of Medical Sciences, B.H.U, Varanasi, India, is acknowledged for providing the space and facilities to perform biological analysis. Jayanta Dowarah acknowledges DST, New Delhi, for DST-inspired fellowship.

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Correspondence to Ved Prakash Singh or Ashish Kumar Tewari.

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Singh, V.P., Dowarah, J., Tewari, A.K. et al. Structural chemistry and anti-inflammatory activity of flexible/restricted phenyl dimers. J IRAN CHEM SOC (2020) doi:10.1007/s13738-020-01853-x

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Keywords

  • Weak interactions
  • Anti-inflammatory activity
  • Docking
  • Interaction energy