Synthesis and anticancer activity of novel quinazolinone and benzamide derivatives

In trying to develop new anticancer agents, a series of quinazolinone and benzamide derivatives were synthesized via reaction of 6-iodo-2-phenyl-4 H -benzoxazin-4-one with nitrogen nucleophiles, namely, formamide, ammonium acetate, hydrazine hydrate, hydroxylamine hydrochloride, substituted aromatic...

Full description

Saved in:
Bibliographic Details
Published in:Research on chemical intermediates 2018-04, Vol.44 (4), p.2545-2559
Main Authors: El-Hashash, Maher Abd El-Aziz Mahmoud, Salem, Marwa Sayed, Al-Mabrook, Selima Ali Mohamed
Format: Article
Language:English
Subjects:
Amines
Ammonium acetate
Anticancer properties
Aromatic compounds
Benzamide
Cancer
Catalysis
Chemical synthesis
Chemistry
Chemistry and Materials Science
Derivatives
Doxorubicin
Inorganic Chemistry
Nitrogen
NMR
Nuclear magnetic resonance
Nucleophiles
Physical Chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:In trying to develop new anticancer agents, a series of quinazolinone and benzamide derivatives were synthesized via reaction of 6-iodo-2-phenyl-4 H -benzoxazin-4-one with nitrogen nucleophiles, namely, formamide, ammonium acetate, hydrazine hydrate, hydroxylamine hydrochloride, substituted aromatic amines, benzyl amine, and/or thiocarbonohydrazide. All compounds were fully characterized by means of IR, MS, and 1 H-NMR spectra. Some of the synthesized compounds were evaluated in vitro for their anti-proliferative activity against HePG-2 and MCF-7 cell lines. 2-(Benzoylamino)- N -(4-hydroxyphenyl)-5-iodobenzamide and tetrazino[1,6-c]quinazoline-3(4 H )-thione derivative were the most potent against the two cancer cells comparable to that of doxorubicin. Most of the synthesized compounds also exhibited good cytotoxic activity.
ISSN:0922-6168
1568-5675
DOI:10.1007/s11164-017-3245-4