Synthesis, in vitro Anticancer Activity Evaluation and Docking Investigations of Novel Aromatic Chalcones

Abstract

Abstract:In a wide search program toward new anticancer agents, a series of Aromatic chalcones have been synthesized by condensing benzaldehyde derivatives with arylmethylcetone in potassium hydroxide ethanol according to the ClaisenSchmidth condensation at room temperature. The synthetic chalcones have been determined by IR spectroscopy and 1H-NMR spectroscopy. The anticancer activitiesof the compounds were evaluated against in vitro using human tumour cell lines of Jurkat and HL-60 cell lines and MTT assay. From the series, two compounds(4,15) exhibited potent growth inhibitory effects against the proliferation of human T-lymphocyte leukemia compared to the parent unsubstitutedchalcone. The result shows that the electron donating groups moiety may increase anticancer activity. Aromatic chalcones with hydroxyl group,methoxy group on A ring at positions 2 or 3 are considered as lead compounds for generation of new potential anticancer drugs in future.Similarly,the compounds(7,12) exhibited potent growth inhibitory effects against HL-60 cells. The results are very encouraging. Future studies include testing the compounds in vivo with and without radiation. Docking studies with 1NKP have shown that the compound 17 has highest IC50 against human leukemia cells (HL-60).

Design, Synthesis and Docking Studies of Flavokawain B Type Chalcones and Their Cytotoxic Effects on MCF-7 and MDA-MB-231 Cell Lines

“…: 171–173 °C (lit. [ 61 ] 173–175 °C); UV-Vis (MeOH) λ max : 342–343 nm; IR (KBr, cm −1 ): 3420 (O-H), 2981–3018 (Ar C-H stretch), 1630 (C=O), 1488–1591 (C=C), 1217–1219 (C-O), 820–822 (C-Cl); 1 H-NMR (600 MHz, CDCl 3 ) δ : 14.24 (s, 1H, OH, C-2′), 7.85 (d, 1H, H-β, J = 15.60 Hz), 7.72 (d, 1H, H-α, J = 15.60 Hz), 7.53 (d, 1H, H-2, J = 8.46 Hz), 7.52 (d, 1H, H-6, J = 8.46 Hz), 7.38 (d, 1H, H-3, J = 8.46 Hz), 7.37 (d, 1H, H-5, J = 8.46 Hz), 6.11 (d, 1H, H-3′, J = 2.40 Hz), 5.96 (d, 1H, H-5′, J = 2.40 Hz), 3.92 (s, 3H, OCH 3 , C-6′), 3.84 (s, 3H, OCH 3 , C-4′); EI-MS: m / z = 318 (57), 301 (7), 283 (2), 207 (100), 181 (34), 165 (13), 152 (19), 137 (25), 111 (6), 102 (20); (Molecular formula C 17 H 15 ClO 4 ).…”