Synthesis of Novel Ethyl (substituted)phenyl‐4‐oxothiazolidin‐3‐yl)‐1‐ethyl‐4‐oxo‐1,4‐dihydroquinoline‐3‐Carboxylates as Potential Anticancer Agents

Abstract

A series of ethyl (substituted)phenyl-4-oxothiazolidin-3-yl)-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylates (7a-g) has been prepared from reactions between aminoquinolones 6 with arenealdehydes and mercaptoacetic acid. The critical intermediates, 6a and 6b, were obtained from appropriate amines by a sequence of steps involving (i) reaction with diethylethoxymethylenemalonate, (ii) thermal cyclization in diphenyl ether, (iii) ethylation and (iv) Pd/C catalyzed reduction. New compounds 7a-g were fully identified and characterized by NMR ( 1 H and 13 C) and specifically for 7d by X-ray crystallography. Compounds 7b-f were found not to exhibit activity at 10 uM concentrations against gastric ascitis (AGP-01), gastric adenocarcinoma kind intestinal (ACP-02), colon (HCT-116) and murine melanome (B16F10) cancer cells. However, none exhibited cytotoxicity against normal cells human fibroblast (MRC-5), murine fibroblast (NIH3T3) and normal human melanocyte (Melan-A).

An ortho-Iminoquinone Compound Reacts with Lysine Inhibiting Aggregation while Remodeling Mature Amyloid Fibrils

“…Purification of the crude product was performed by column chromatography (silica gel, hexane/EtOAc) affording the pure 1-(3-Amino-2,4-dihydroxyphenyl)-1-ethanone in 72% yield (0.92 g, 4.7 mmol). This compound (1.0 g, 5.0 mmol) was poured into a hydrogenation flask, followed by the addition of Pt/C (0.1 g, 10 mol %), and the mixture was subjected to hydrogenation at 28 atm (420 psi) at 50 °C . The reaction was monitored by TLC until total conversion of the starting material was achieved.…”

Quinoline‐based thiazolidinone derivatives as potent cytotoxic and apoptosis‐inducing agents through EGFR inhibition

“…Also, it was reported that some quinoline analogues bearing thiazolidine moiety have apoptotic activity and acts as kinase inhibitors for the treatment of colorectal cancer (Bathula et al, 2016; Finiuk et al, 2017; Kobylinska et al, 2019; Senkiv et al, 2016; Zhang et al, 2014; Zhou et al, 2021). Attaching thiazole to quinoline nucleus is expected to increase the overall compound activity (Aly et al, 2020; Andreani et al, 2005; Erguc et al, 2018; Facchinetti et al, 2015; Ghorab et al, 2016); this encouraged us to test the anticancer activity of previously synthesized derivatives (Amer et al, 2018) through apoptosis induction.…”