Anticancer activity of novel Schiff bases and azo dyes derived from 3-amino-4-hydroxy-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione

Shaikha S. AlNeyadi,Ibrahim M. Abdou,Abdeltawab Mohamed Saeed

doi:10.1515/hc-2020-0116

Abstract

Abstract New Schiff bases and azo dyes derivatives have been synthesized via appropriate conventional methods using pyranoquinolinone as a starting material. The compounds obtained were characterized by spectral analysis and evaluated for anticancer activity in several human tumor cell lines: MCF-7 breast cancer, HepG2 liver cancer and HCT-116 colon carcinoma. 5-fluorouracil was used as a reference drug. The in vitro cytotoxicity screening results revealed that all tested compounds showed promising activity against MCF-7 cells. In particular, compounds 6a, 6b, and 7b showed excellent activity against the three human tumor cell lines. Structure-activity relationship studies indicated that the azo derivative with a trifluoromethoxy group (compound 7b) was the most potent candidate against the three human tumor cell lines (IC50, 1.82-8.06 μg/mL). Our findings highlight pyranoquinolinone analogues as a promising class of compounds for new anticancer therapies.

Highlights

Heterocyclic systems containing a quinolone nucleus represent an important group of compounds in medicinal and pharmaceutical chemistry
New Schiff bases and azo dyes derivatives have been synthesized via appropriate conventional methods using pyranoquinolinone as a starting material
Some pyranoquinolinone-based Schiff bases exhibit significantly better TOP2B inhibitory activity against MCF-7 breast cancer cells compared to doxorubicin [8]

Summary

Introduction

Heterocyclic systems containing a quinolone nucleus represent an important group of compounds in medicinal and pharmaceutical chemistry. Pyranoquinoline alkaloid compounds containing pyrano[3,2-c]quinolone as the parent ring structure have received significant attention due to their broad spectrum of antimicrobial [1,2,3], anti-inflammatory [4], antimalarial [5], antifungal [6] and anticancer properties [7]. In addition to these bioactivities, 6-n-butylpyranoquinolone derivatives are highly selective Topoisomerase II beta (TOP2B) inhibitors [8] which inhibit growth of different tumor cell lines [9] and are potential anti-cancer agents [10].

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Conclusion