Synthesis Of 2-Styryl Derivatives of N, N-Bis-Substituted Quinazolines
Harutyunyan Artur A1,2*, Ghukasyan Gohar T1 and Danagulyan Gevorg G1,2
1 Russian Armenian (Slavonic) University, Armenia, Asia
2 Scientific and technological center of organic and pharmaceutical chemistry, Russian Armenian (Slavonic) University, Armenia, Asia
Submission: July 28, 2018; Published: August 03, 2018
*Corresponding author: Harutyunyan Artur A, Russian Armenian (Slavonic) University, Armenia, Asia; Email: firstname.lastname@example.org
How to cite this article: Harutyunyan Artur A*, Ghukasyan Gohar T and Danagulyan Gevorg G. Synthesis Of 2-Styryl Derivatives of N, N-Bis-Substituted Quinazolines. Organic & Medicinal Chem IJ. 2018; 7(4): 555718. DOI: 10.19080/OMCIJ.2018.07.555718
Interest in the heterocyclic quinazoline system is largely due to the high biological activity that they exhibit, including anti protozoic, anti-inflammatory, sedative, antibacterial, as well as the ability to inhibit kinases, the aurora-serine/threonine kinase involved in the regulation of cell division . In recent works, attention has been drawn to the substituted 2-styrylquinazolines, showing antibacterial, fungicidal and cytotoxic properties  and bis-quinazolines - inhibitors of the epidermal growth factor receptor (EGFR) . In connection with this, in the continuation of our investigations , we synthesized substituted quinazolines, combining the above structural fragments - 2-(2-arylvinyl)-3,3’-(ethane-1,2-, butane-1,4-, hexane-1,6-diylbis [2-[(E)-2-arylvinyl]quinazolin-4(3H)-ones] and 3,3’-[imino-bis(ethane-2,1-diyl)]bis[2-[(E)-2-arylvinyl]-quinazoline-4(3H)-ones], according to the scheme: 2: n = 0; 3,6a,b: n = 1; 4,7a-e: n = 2; 6a,b: R= 4-ClC6H4 (a), 2,4-Cl2C6H3 (b); 7a-e: R= Ph (a), 4-FC6H4 (b), 2,4-Cl2C6H3 (c), pyridin-3-yl (d), thiophen-2-yl (e); 8a,b: R = Ph (a), 4-NO2C6H4 (b).
The reaction of 2-methyl-4H-3,1-benzoxazin-4-one 1 with the corresponding diamines in the ratio 2/1 under heating conditions in poly phosphoric acid yielded 3,3’-bis [(2-methylquinazolin) -4 (3H) -ones] 2-5. The latter are condensed with aromatic and heterocyclic aldehydes by co-heating or by boiling in acetic anhydride to give the desired compounds 6a, b,7a-e and 8a, b. The structure of the synthesized compounds was proved by IR and NMR 1H-spectroscopy. Some of the bis-quinazolines studied showed a weak, and bis-4-nitro derivative 8b is a moderate antibacterial action against four strains of Gram-positive and Gram-negative microorganisms, and some compounds also detected a noticeable anti mono amino oxidase activity.
- Ajani OO, Audu OY, Aderohunmu DV, Owolabi EO, Olomieja AO (2017) Am J Drug Discov Dev 7(1): 1-24.
- Agbo EN, Makhafola TJ, Choong YS, Mphahlele MJ, Ramasami PR (2016) Molecules 21: 28-43.
- Wu Y, Niu C, Zou D, Li J, Guo R (2014) US Patent US 8(916): 572.
- Danagulyan Gevorg G, Harutyunyan Artur A, Ghukasyan Gohar T (2018) Synthesis of 2-styryl derivatives substituted quinazolines. International Conference 100 Years of Development of Chemistry: From Synthesis of Polyethylene to Stereo divergence 16(18): 103-105.