Synthesis of Novel β-Keto-Enol Derivatives Tethered Pyrazole, Pyridine and Furan as New Potential Antifungal and Anti-Breast Cancer Agents

Abstract

Abstract:Recently, a new generation of highly promising inhibitors bearing β-keto-enol functionality has emerged. Reported herein is the first synthesis and use of novel designed drugs based on the β-keto-enol group embedded with heterocyclic moieties such as pyrazole, pyridine, and furan, prepared in a one-step procedure by mixed Claisen condensation. All the newly synthesized compounds were characterized by FT-IR, 1 H-NMR, 13 C-NMR, ESI/LC-MS, elemental analysis, and evaluated for their in vitro antiproliferative activity against breast cancer (MDA-MB241) human cell lines and fungal strains (Fusarium oxysporum f.sp albedinis FAO). Three of the synthesized compounds showed potent activity against fungal strains with IC 50 values in the range of 0.055-0.092 µM. The results revealed that these compounds showed better IC 50 values while compared with positive controls.

Crystal structure of (Z)-1-(1,5-dimethyl-1H-pyrazol-3-yl)-3-(4-ethoxyphenyl)-3-hydroxyprop-2-en-1-one, C16H18N2O3

“…Some β-keto-enols containing a pyrazolyl moiety are of interest for their use in synthetic procedures [1], their remarkable biological activities [2] and e cient coordination properties [3]. The crystal structure shows the formation of an intramolecular (O1-H-O2) interaction balancing the intraelectrostatic forces and van der Waals interactions.…”

Crystal structure of (Z)-1-(1,5-dimethyl-1H-pyrazol-3-yl)-3-hydroxy-3-(4-methoxyphenyl)prop-2-en-1-one, C15H16N2O3

“…Some heterocyclic compounds bearing β-keto-enol functionality have recently attracted a great attention due to their applications in organic and inorganic chemistry [1][2][3][4]. In this work we coupled ethyl pyrazole carboxylate with pOMe-phenyl methyl ketone to produce the title compound in acceptable yield.…”

β-Keto-enol Tethered Pyridine and Thiophene: Synthesis, Crystal Structure Determination and Its Organic Immobilization on Silica for Efficient Solid-Liquid Extraction of Heavy Metals

“…The product was obtained using a procedure similar to that described in our recent previous work [20]. The β-keto-enol form was determined using 1 H-NMR, showing a strong signal assigned to the =C-H group of the keto-enol form and a negligible signal attributed to the CH2 group of the diketone form.…”