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Description
Although curcumin (CUR) has significant beneficial effects and biological activity, its clinical applications are limited due to its poor bioavailability, low absorption, rapid metabolism and low chemical stability. One approach to enhance the bioavailability of CUR is through the structural modification of its molecule. C5-curcuminoids (C5-CUR) that lack a β-diketone moiety in their structure possess greater metabolic stability and bioactivity than CUR, increased stability in vitro, and improved pharmacokinetic profile in vivo. These compounds have been extensively studied and exhibit various beneficial biological properties.
In this study, six C5-CUR were synthesized and their biological activity was predicted in silico using the online platforms SwissADME and Protox-3.0. The synthesis was carried out via Claisen-Schmidt condensation reaction between various aromatic aldehydes and acetone, catalyzed by sodium hydroxide. The synthesized compounds were characterized using melting points and spectroscopic techniques. The indicative spectroscopic characteristics of these cross-conjugated derivatives is the C=O stretching band that is below 1700 cm-1. They all show UV-Vis absorption peak above 300 nm.
The drug-likeness analysis confirmed that most of the synthesized compound fulfilled the criteria of Lipinski’s Rule of Five, indicating favorable pharmacokinetic properties and potential oral bioavailability. Furthermore, the in silico toxicity assessment revealed a low predicted toxicological risk, suggesting that the synthesized C5-curcuminoid derivatives represent promising candidates for further biological evaluation.
Keywords: C5-curcuminoids, spectroscopic properties, in silico analysis.