Phosphonate Derivatives of 3,5-bis(arylidene)-4-piperidone: Synthesis and Biological Evaluation

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Author(s): Shweta Mishra, Debashree Das, Adarsh Sahu, Shailendra Patil, Ram Kishore Agrawal, Asmita Gajbhiye*.

Journal Name: Anti-Infective Agents
Anti-Infective Agents in Medicinal Chemistry

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Background: 3,5-Bis(arylidene)-4-piperidinones belong to a wide class of cross conjugated dienones and contain a The 1,5-diaryl-3-oxo-1,4-pentadienyl fragment of the BAP moiety is responsible for the molecule's anti-tumor, antioxidant, antimicrobial and anti-inflammatory manifestations. In the present study, we present combinations of phosphonate and 3,5-bis(arylidene)-4-piperidone pharmacophores. The anti-inflammatory, anti-oxidant potential, anti-proliferative, cytotoxic potential and antimicrobial of the title compounds were evaluated in in-vitro bioassay paradigms.

Methods: A novel class of phosphonate linked 3,5-Bis(aryl methylene)-4-piperidone derivatives were synthesized from simple, versitalie and efficient synthetic methodology. All of the synthesized compounds were screened for their anti-inflammatory and in-vitro antioxidant activity. Amongst all synthesized compounds in series, phosphonate derivatives of 3,5-Bis(arylmethylene)-4-piperidone containing 4-hydroxy-3-methoxyphenyl curcumin like prototype were more active than phenyl substituted compounds.

Results: The results of the screening revealed that compounds 5e, 5f, 5g, 5h were more active candidates as compared to 5a, 5b, 5c and 5d, however 5d can be readily endorsed as the most active compound of the series. Structure- activity relationship of the synthesized series suggested that structural resemblance of the synthesized compounds with that of curcumin was enormously accountable for the compounds anti-inflammatory, antioxidant and cytotoxic potential activity.

Conclusion: The in-vitro biological spectrum indicated that the substitution of groups at third and fourth position and alkyl phosphonates substitution potentiates the activity as compared to curcumin.

Keywords: 4-Piperidonone, curcumin, Phosphonates, 3, 5-bis(arylidene)-4-piperidone, Anti-inflammatory activity, Antioxidant activity

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(E-pub Ahead of Print)
DOI: 10.2174/2211352517666190820143735