Semi-synthesis of phenolic-amides and their cytotoxicity against THP-1, HeLa, HepG2 and MCF-7 cell lines

Abstract

In the present study, we derivatized several hydroxycinnamic and hydroxybenzoic acids to phenolic amides (PAMs) via one step BOP mediated amide coupling reactions. Fifteen PAMs were synthesized in >40% yields and were screened for their cytotoxic activities against four cancer cell lines: THP-1 (leukemia), HeLa (cervical), HepG2 (liver), and MCF-7 (breast), in comparison to 5-flurouracil (5-FU). Four amides showed IC50 ranging from 5 to 55 µM against all four cell lines. In contrast, tetradecyl-gallic-amide (13) affected only THP-1 leukemia cells with IC50 of 3.08 µM. The activities of these compounds support the promise of phenolic amides as anticancer agents.

Anti-proliferative Effects of Pinocembrin Isolated From Anomianthus dulcis on Hepatocellular Carcinoma Cells

“…Cytotoxicity of the compounds was examined with sulforhodamine B (SRB) assay following standard protocol with some modifications as following details. 9 Cells (1 × 10 3 cells/well) 10 , 11 were seeded into a 96-well plate and incubated overnight. Then, the media were replaced with media containing various concentrations of the specified compounds and incubated further for 72 hours while 0.3% dimethyl sulfoxide (DMSO) was used as a vehicle control.…”

Sustainable Chemical Derivatization of Hydroxycinnamic Acids

“…These include phenol protection [15] and acyl chloride formation followed by coupling with amines or alcohols. [16] Common coupling reagents involve phosphonium and uronium salts like BOP [17] and HATU [18] or carbodiimides such as DCC [19] or EDC [20] in the presence of additives such as HOBt and HOAt.…”