Journal Title
Title of Journal: Med Chem Res
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Abbravation: Medicinal Chemistry Research
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Authors: Neha Singh Avinash C Tripathi Aseem Tewari Ravi Kumar Shailendra K Saraf
Publish Date: 2014/09/25
Volume: 24, Issue: 5, Pages: 1927-1941
Abstract
A series of new 5aryliden2imino4thiazolidinones 5a–e and 6a–e were synthesized via a threestep reaction and characterized by physicochemical and spectral data The uniqueness of the derivatives lies in the fact that none of them had an acidic group like conventional NSAIDS but exhibited significant in vivo activity in acute inflammation models In particular 53chlorobenzyliden2pyridin2ylimino4thiazolidinone5a and 53chlorobenzyliden25methylisoxazol3ylimino4thiazolidinone 6a showed remarkable paw oedema inhibition 6776 and 7447 oedema inhibition respectively after 3 h comparable to that of Ibuprofen 7456 oedema inhibition after 3 h at half of the dose of the standard drug Also compounds 5a 7286 and 6a 8020 were found to possess significant inhibition of albumin denaturation when screened for in vitro antiinflammatory activity In addition these compounds were docked into the known active site of COX2 protein using Glide XP and QPLD algorithms and the bindingfree energy was calculated using Prime MM/GBSA simulation methods The combined use of molecular docking and MM/GBSA methods gave a good correlation between the predicted bindingfree energy and experimentally determined biological activities It was also evident from the docking results that 2methylisoxazolylimino or 2pyridin2ylimino substitution and 3chloro moiety on 5benzylidin nucleus of these 4thiazolidinone derivatives can easily occupy the COX2 binding pocket considered as the critical interaction for COX2 inhibition Moreover pharmacokinetic properties of all the synthesized compounds were predicted with good results Further the synthesized derivatives showed neither acute toxicity nor symptoms of gastric ulceration at extended doses owing to the absence of an acidic group
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