Design, Synthesis And Evaluation Of New Chemosensors Containing Quinazolinones Moiety For Ions In An Aqueous Medium And Biological Samples

Life Sciences-Chemistry for New drug discovery

Abstract

Quinazolinone derivatives were reported as a varied range of biological activity and played a principal part metabolism of all biological systems. The quinazolinone is an organic compound ring containing two merged aromatic rings benzene and pyrimidine. The current project deals with the design and synthesizing new Quinazolinones derivatives and evaluate them as colorimetric chemosensors to detect the cations in the aqueous medium and biological sample. The synthetic strategy depends on acylation of anthranilic acid (1) with butyroyl chloride followed by ring closure to yield benzoxazinone (2), which was reacted with various nucleophiles hydrazine hydrate, urea, thiourea, p-aminophenol, hydroxylamine, and phenyl hydrazine to give corresponding quinazolinone chemosensors 3-amino-2-propylquinazolin-4(3H)-ones (4), 6-nitro-4-oxo-2-propylquinazoline-3(4H)-carboxamide (5a), 6-nitro-4-oxo-2-ropylquinazoline-3(4H)-carbothioamide (5b), 3-(2-hydroxyphenyl)-6-nitro-2-propylquinazolin-4(3H)-one (6), 3-hydroxy-2-propylquinazolin-4(3H)-ones (7) and 6-nitro-3-(phenylamino)-2-propylquinazolin-4(3H)-one (8). The importance of producing chemosensors has increased in the last decade. Therefore, here we developed and synthesized chemosensors 4 and 8 with highselectivity and specificity to detect copper and mercury in both aqueous solutions and blood samples. Where the results showed that chemosesors 4 and 8 exhibited colormetric responses from pale yellow to green in case of Cu2+ ions and exhibited remarkable color change from pale yellow to rose by interacting with Hg2+. Chemosensors 5b and 7 show high selectivity toward cadmium ion, whereas chemosensors 5b and 7 exhibited remarkable color change from colorless to yellow when adding Cd2+. but the synthesized compounds 5a and 6 did not exhibit colorimetric response in all cation's samples. In addition, the synthesized chemosensor was established as a strip paper to make the measurement process easy and inexpensive. All the synthesized compounds have been established by instrumental spectroscopy; 1HNMR, 13CNMR, IR, and mass spectra (ms).