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      https://www.ias.ac.in/article/fulltext/jcsc/129/05/0623-0636

    • Keywords

       

      Bis-allyloxy derivatives; hydroxypropoxy derivatives; 4,5-diarylthiophene-2-carboxylic acid; anti-inflammatory; antioxidant; molecular docking.

    • Abstract

       

      In our earlier studies, we have shown that the introduction of amino moieties at carboxylic acid of 4,5-diarylthiophene-2-carboxylic acid significantly improved the anti-inflammatory activity of the compound against the standard drug diclofenac sodium. In the present study, we have synthesized new derivatives of 4,5- diarylthiophene-2-carboxylic acid by modifying the hydroxyl group of the phenyl ring and carboxylic acid group of the thiophene ring.Aseries of novel 4,5-diarylthiophene-2-carboxylic acid derivatives containing bis-allyloxyand hydroxypropoxy with methyl or ethyl ester moieties were synthesized, characterized and subsequently evaluated for anti-inflammatory and antioxidant property. Among the novel compounds, the inhibition of bovineserum albumin denaturation assay revealed that the compound 4,5-bis(4-(3-hydroxypropoxy)phenyl)thiophene- 2-carboxylic acid (15) and ethyl ester (13) having anti-inflammatory activity better than the standard drugdiclofenac sodium. The antioxidant screening showing 4,5-bis(4-(allyloxy)phenyl)thiophene-2-carboxylic acid (10), 4,5-bis(4-(3-hydroxypropoxy)phenyl)thiophene-2-carboxylic acid methyl ester (11) and 4,5-bis(4-(3- hydroxypropoxy)phenyl)thiophene-2-carboxylic acid ethyl ester (13) exhibited a slightly moderate antioxidant activity than standard ascorbic acid. Molecular docking analysis was performed for the synthesized compounds with the cyclooxygenase-2 (COX-2) receptor (PDB 1D: 1PXX). Docking studies revealed that all the synthesised compounds exhibit greater binding affinity than the standard drug. Particularly, the compound ethyl 4,5-bis(4- (allyloxy)phenyl)thiophene-2-carboxylate (8) and allyl 4,5-bis(4-(allyloxy)phenyl)thiophene-2-carboxylate (9) having high free energy binding of −10.40 and −10.48 Kcal/mol, respectively.

    • Author Affiliations

       

      T SHANMUGANATHAN1 2 M VENUGOPAL3 K PARTHASARATHY4 N DHATCHANAMOORTHY1 Y ARUN5 A A M PRINCE2

      1. Orchid Pharma Ltd, R&D Centre, Chennai, Tamilnadu 600 119, India
      2. Department of chemistry, Ramakrishna Mission Vivekananda College, Mylapore, Chennai, Tamilnadu 600 004, India
      3. Ven Biotech Private Limited, Chennai, Tamilnadu 600 095, India
      4. Department of Chemistry, Siddha Central Research Institute, Central Council for Research in Siddha, Chennai, Tamilnadu 600 106, India
      5. Organic Chemistry Division, Central Leather Research Institute (CSIR), Adyar, Chennai, Tamilnadu 600 020, India
    • Dates

       
    • Supplementary Material

       
  • Journal of Chemical Sciences | News

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