A Series of 2,4(1H,3H)-Quinazolinedione Derivatives: Synthesis and Biological Evaluation as Potential Anticancer Agents

Abstract

A series of 6,7-disubstituted-3-{2-[4-(substituted)piperazin-1-yl]-2-oxoethyl}quinazoline-2,4(1H,3H)-dione derivatives (7-34) were synthesized and their structures were elucidated on the basis of analytical and spectral (UV, IR, 1 H-NMR, 13 C-NMR and MS) data. These synthesized compounds were evaluated for their in vitro cytotoxicities against a panel of three human cancer cell lines. According to the cytotoxicity screening results, 3-{2-[4-(4-chlorobenzyl)piperazin-1-yl]-2-oxoethyl} quinazoline-2,4(1H,3H)-dione (7) presented the highest activity against HUH-7, MCF-7 and HCT-116 cell line with the IC 50 values of 2.5, 6.8 and 4.9 µM, respectively.

Advanced zeolite and ordered mesoporous silica-based catalysts for the conversion of CO2to chemicals and fuels

“…Quinazoline-2,4(1H,3H)-dione constitutes an important class of nitrogen-containing heterocycles with biological activities that find a large number of applications as pharmaceuticals. [316][317][318][319] The synthesis of quinazoline-2,4(1H,3H)-dione derivatives starting from non-toxic, low cost and readily available substrates such as CO 2 and 2-aminobenzonitrile is of great interest and constitutes an environmentally friendly process with 100% atom efficiency and an alternative route to the use of toxic phosgene, carbamates, 320 anthranilic acids with urea, 321,322 potassium cyanate and chlorosulfonyl isocyanate. 319 A new, straightforward and overall green synthetic route of quinazoline-2,4(1H,3H)-dione in the presence of DBU has been reported.…”

Rational Design and Lead Optimisation of Potent Antimalarial Quinazolinediones and Their Cytotoxicity against MCF-7

“…It is well evident that quinazolinedione derivatives possess anticancer activity. Akgun et al reported the synthesis of quinazolinedione derivatives and their antiproliferative activities against three different cancer cell lines, and the results showed that some derivatives exhibited cytotoxicity below 10 µM [ 19 ]. Compound 3 ( Figure 1 ) and related compounds, which are 3-substituted-2,4-quinazolinedione derivatives, are patented for their highly potent cytotoxicity against human ovarian cancer (SKOV3) [ 20 ].…”

Identification of Spiro-Fused [3-azabicyclo[3.1.0]hexane]oxindoles as Potential Antitumor Agents: Initial In Vitro Evaluation of Anti-Proliferative Effect and Actin Cytoskeleton Transformation in 3T3 and 3T3-SV40 Fibroblast

“…Cancer is one of the fatal diseases, which is characterized by uncontrolled cell division leading to metastasis and invasion into adjacent tissues. Synthesizing new anticancer agents with less side effects and increased selectivity is still a developing area of interest in medicinal chemistry [ 1 ]. A significant portion of the improved clinical outcomes in cancer can be attributed to refined chemotherapeutic agents.…”