Synthetic Derivatives of Curcumin and their Activity against Leishmania amazonensis

Abstract

Summary In a previous work, the in vitro and in vivo activity of a series of diarylheptanoid derivatives against Leishmania amazonensis has been described. Based on the promising results, ten new compounds belonging to the same chemical class were synthesized and have been investigated in relation to their leishmanicidal activity. The compounds were obtained through several chemical modifications on the basic structure of curcumin (1,7-bis-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione) in an attempt to increase its effectiveness and decrease the potential toxic effects. The drugs were assayed in vitro against L. amazonensis promastigotes and using pentamidine isethionate as reference drug. The results showed that the most effective compound is 1,7-bis-(4-propargyl-3-methoxyphenyl)-1,6-heptadiene-3,5-dione, which is about ten times more efficient than the original curcumin. Nevertheless, these results did not allow us to make any correlation between the leishmanicidal activity and the chemical structure of the compounds.

Curcuminoid–BF2 complexes: Synthesis, fluorescence and optimization of BF2 group cleavage

“…Comparison with data reported in the literature [31] as well as the absence of a 19 F{ 1 H} NMR signal proved the success of the reaction. As expected, in the control reaction in dry THF no cleavage reaction was observed.…”

“…Complex 2b was chosen as the model compound (Scheme 2) as 3b has been previously reported in the literature [31]. …”

A Clinical Study of Surgical Management of Diaphyseal Fractures of Tibia With Intramedullary Interlocking Nail

“…The present study is taken up to evaluate the anti-diabetic effect of Turmeric which is rich in active ingredient Curcumin. From the earlier studies, it was found that Turmeric is known to possess anti-diabetic properties 40,41 . Our standard anti diabetic drug, Pioglitazone, acts on PPAR-γ which is present primarily in adipose tissue and less in cardiac, skeletal, smooth muscle cells, islet β cells, macrophages and vascular endothelial cells.…”

Carotenoids: biochemistry, pharmacology and treatment

“…This compound is different from other curcumin derivatives, which mostly stimulate cell apoptosis (Zhou et al ., ). Also, other synthetic derivatives of curcumin, including compounds 4 [1, 7‐bis‐(3,4‐dimethoxyphenyl)‐1,6‐heptadiene‐ 3,5‐dione] and 8 [1, 7‐bis‐(4‐propargyl‐3‐methoxyphenyl)‐1,6‐ heptadiene‐3,5‐dione], have been found to have potent activity against Leishmania amazonensis (Gomes et al ., ). Curcumin and its analogues have been demonstrated to have an inhibitory effect on AP‐1 transcription (responsible for cell proliferation and differentiation) and anti‐angiogenic activity on the developmental neovascularization of chick embryo.…”