One-Pot Synthesis of Novel Furochromone and Oxazocine Derivatives as Promising Antitumor Agents with Their Molecular Docking Studies

Abstract

One-pot efficient synthesis of novel chromone derivatives 4a–h and that of 5a–h were described in a simple method via four-component reaction between furochromone carbaldehyde, amine, isocyanate derivatives, and benzoic acid derivatives or nicotinic acid, respectively. Also, oxazocine derivatives 7a, b were prepared via reaction of visnagine carbaldehyde, ethyl acetoacetate and isocyanate derivatives 2a, b. The obtained derivatives of novel furochromone and oxazocine derivatives were evaluated as promising antitumor agents against panel of two human cell lines, hepatocellular carcinoma (HEPG2) and breast carcinoma (MCF7). The antitumor results suggested that furochromone derivatives 5a–h have activity against MCF7 in comparison with doxorubicin as the standard drug. Furthermore, the molecular docking studies of these novel derivatives of furochromone and oxazocine showed good agreement with the biological results when their binding pattern and affinity towards the active site of EGFR was investigate.

Recent advances in [4 + 4] annulation of conjugated heterodienes with 1,4-dipolar species for the synthesis of eight-membered heterocycles

“…Numerous oxazocine derivatives have been reported to be useful for their unique biomedicinal properties such as antitumor, anti-inflammatory, κ-opioid agonistic, and NK 1 receptor antagonistic activities. 56 In recent years, several series of oxazocine derivatives have been assembled from cascade reactions through [4 + 4] annulation. [57][58][59][60] In the presence of Pd 0 and a base, (2-hydroxymethyl)allyl carbonate could be converted to a 1,4-dipolar π-allylpalladium complex through an oxidative addition/decarboxylation/deprotonation process.…”

POTENTIAL OF IMIDAZOLE-CONTAINING DERIVATIVES FOR PRACTICAL APPLICATION (Review)

“…Полученные производные фурохрома и оксазоцина оценены на активность на двух линиях клеток человекапротив гепатоцеллюлярной карциномы (Hep G2) и рака молочной железы (MCF7). Результаты показали, что производные фурохрома (14 а-һ) активны против MCF7 по сравнению со стандартным препаратом доксорубицином [14]. Кроме того, молекулярная стыковка новых производных фурохрома и оксазоцина показала хорошую корреляцию со своими биологическими результатами при изучении характера их связывания и близости к активному сайту EGFR (PDB ID:5CAV) методом молекулярного докинга с использованием программы MOE 2008.10.…”