Synthesis and Biological Activities of N -Alkyl Derivatives of o-, m-, and p-Nitro (E)-4-Azachalcones and Stereoselective Photochemistry in Solution, with Theoretical Calculations

Authors : Nurettin YAYLI, Osman ÜÇÜNCÜ, Ahmet YAŞAR, Murat KÜÇÜK, Nuran YAYLI, Emine AKYÜZ, Şengül ALPAY KARAOĞLU

Pages : 505-514

View : 20 | Download : 9

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :The N-alkyl derivatisation and photochemical dimerisation of 3 o-, m-, and p-nitro substituted 4-azachalcones insert ignore into journalissuearticles values(1-3); yielded 3 new o-, m-, and p-nitro substituted insert ignore into journalissuearticles values(E);-N-decyl-4-azachalconium bromides, insert ignore into journalissuearticles values(2E);-1-insert ignore into journalissuearticles values(2-nitrophenyl);-3-insert ignore into journalissuearticles values(N-decyl-4-pyridinium bromide);-2-propen-1-one insert ignore into journalissuearticles values(4);, insert ignore into journalissuearticles values(2E);-1-insert ignore into journalissuearticles values(3-nitrophenyl);-3-insert ignore into journalissuearticles values(N-decyl-4-pyridinium bromide);-2-propen- 1-one insert ignore into journalissuearticles values(5);, and insert ignore into journalissuearticles values(2E);-1-insert ignore into journalissuearticles values(4-nitrophenyl);-3-insert ignore into journalissuearticles values(N-decyl-4-pyridinium bromide);- 2-propen-1-one insert ignore into journalissuearticles values(6);, and 3 new dimers in solution, insert ignore into journalissuearticles values(1b, 2a);-di- insert ignore into journalissuearticles values(3-nitrobenzoyl);-insert ignore into journalissuearticles values(3b, 4a);-di-insert ignore into journalissuearticles values(4-pyridinyl); cyclobutane insert ignore into journalissuearticles values(7);, insert ignore into journalissuearticles values(1b, 2a);-di-insert ignore into journalissuearticles values(4-nitrobenzoyl);-insert ignore into journalissuearticles values(3b,4a);-di-insert ignore into journalissuearticles values(4-pyridinyl); cyclobutane insert ignore into journalissuearticles values(8a);, and insert ignore into journalissuearticles values(1b, 2b);-di-insert ignore into journalissuearticles values(4-nitrobenzoyl);-insert ignore into journalissuearticles values(3b, 4a);-di-insert ignore into journalissuearticles values(4-pyridinyl);cyclobutane insert ignore into journalissuearticles values(8b);, stereoselectively. The monomeric compounds showed good antimicrobial activity against test micro-organisms. The most sensitive micro-organisms were Gram-positive bacteria. The monomers also showed high antioxidant activity, while the dimerisation products 7-8a,b were less active. Compound 6 was found to have similar or even higher activity when compared to the standard antioxidants TroloxR and vitamin C, respectively. The possible dimerisation products of compounds 1-3 were calculated theoretically. Experimental and theoretical calculations showed that d-truxinic type dimer is the most stable isomer.
Keywords : Nitro E, 4 azachalcones, nitro E, N decyl 4 azachalconium bromide, photodimerisation, antimicrobial and antioxidant activities