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

  • Ved Prakash SinghEmail author
  • Jayanta Dowarah
  • Ashish Kumar TewariEmail author
  • David K. Geiger
Original Paper

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) (Tewari et al. Acta Cryst. E63:o1930, 2007) [1] (4) and 4-(2-Phenoxy-ethoxy)-benzaldehyde (C15H14O3) (Valgera et al. CCDC 710835, 2016) [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.

Keywords

Weak interactions Anti-inflammatory activity Docking Interaction energy 

Notes

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.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

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Supplementary material 1 (DOCX 4100 kb)
13738_2020_1853_MOESM2_ESM.docx (2.6 mb)
Supplementary material 2 (DOCX 2635 kb)

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Copyright information

© Iranian Chemical Society 2020

Authors and Affiliations

  1. 1.Department of Chemistry, School of Physical SciencesMizoram UniversityAizawlIndia
  2. 2.Department of Chemistry, Institute of ScienceBanaras Hindu UniversityVaranasiIndia
  3. 3.Department of Chemistry, College of GenescoState University of New YorkGenescoUSA

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