Background: 3,5-Bis(arylidene)-4-piperidinones (BAP) belong to a wide class of cross
conjugated dienones. 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 in vitro anti-inflammatory, in vitro anti-oxidant potential,
in vitro anti-proliferative, in vitro cytotoxic potential and in vitro antimicrobial activity. Amongst
all the 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.