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

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

The N-alkyl derivatisation and photochemical dimerisation of 3 o-, m-, and p-nitro substituted 4-azachalcones (1-3) yielded 3 new o-, m-, and p-nitro substituted (E)-N-decyl-4-azachalconium bromides, (2E)-1-(2-nitrophenyl)-3-(N-decyl-4-pyridinium bromide)-2-propen-1-one (4), (2E)-1-(3-nitrophenyl)-3-(N-decyl-4-pyridinium bromide)-2-propen- 1-one (5), and (2E)-1-(4-nitrophenyl)-3-(N-decyl-4-pyridinium bromide)- 2-propen-1-one (6), and 3 new dimers in solution, (1b, 2a)-di- (3-nitrobenzoyl)-(3b, 4a)-di-(4-pyridinyl) cyclobutane (7), (1b, 2a)-di-(4-nitrobenzoyl)-(3b,4a)-di-(4-pyridinyl) cyclobutane (8a), and (1b, 2b)-di-(4-nitrobenzoyl)-(3b, 4a)-di-(4-pyridinyl)cyclobutane (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.

Anahtar Kelimeler:

Nitro-(E)-4-azachalcones, nitro-(E)-N-decyl-4-azachalconium bromide, photodimerisation, antimicrobial and antioxidant activities

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

Keywords:

Nitro-(E)-4-azachalcones, nitro-(E)-N-decyl-4-azachalconium bromide, photodimerisation, antimicrobial and antioxidant activities,

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J.B. Harborne, “The Flavonoids, Advances in Research”, Chapman & Hall, New York NY, 329-388, 1988.
J.P.J. Marais, D. Ferreira and D. Slade, Phytochemistry 66, 2145-2176 (2005).
Z. Nowakowska, E. Wyrzykiewicz and B. Kedzia, Il Farmaco 56, 325–329 (2001).
M.L. Edwards, D.M. Stemarick, J.S. Sabol, K.A. Diekema and R.J. Dinerstein, J. Med. Chem. 37, 4357-4362 (1994).
M. D’Auira and R. Racioppi, Tetrahedron 53, 17307-17316 (1997).
M. D’Auria, L. Emanuele, V. Esposito and R. Racioppi, Arkivoc (xi), 65-78 (2002).
M. D’Auria, Heterocycles, 54, 475-496 (2000).
M. D’Auria, L. Emanuele, G. Mauriello and R. Racioppi, J. Photochem. Photobiol. A, 134, 147-154 (2000).
N. Yaylı, A. Ya¸sar, O. ¨U¸c¨unc¨u, S. ¨O. Sivrikaya, C. G¨ule¸c, M. K¨u¸c¨uk and R. Abbasov, J. Photochem. Photobiol. A, 175, 291-298 (2005).
N. Yaylı, O. ¨U¸c¨unc¨u, A. Ya¸sar, Y. G¨ok, M. K¨u¸c¨uk and S. Kolaylı, Tu rk. J. Chem., 28, 515-521 (2004).
N. Yaylı, O. ¨U¸c¨unc¨u, E. Aydın, Y. G¨ok, A. Ya¸sar, C. Baltacı, N. Yıldırım and M. K¨u¸c¨uk, J. Photochem. Photobiol. A, 169, 229-234 (2005).
V. Seidel, F. Bailleul and P.G. Waterman, Phytochemistry 55, 439-446 (2000).
D.R. Katerere, A.I. Gray, A.R. Kennedy, R.J. Nash and R.D. Waigh, Phytochemistry 65, 433-438 (2004).
M. D’Auria and R. Racioppi, J. Photochem. Photobiol. A, 112, 145-148 (1998).
J. Durinda, L. Szucs, J. Kolena, A. Nagy, E. Misikova and J. Heger, Czech. Cesko-Slov. Farmac. 26, 140-149 (1977).
V.L. Aeppli, K. Bernuuer, F. Schneider, K. Strub, W.E. Oberhansli and K.H. Pfoertner, Helv. Chim. Acta , 630-644 (1980).
Z. Zhang, Y.W. Dong and G.W. Wang, Chem. Lett. 32, 966-967 (2003).
Z. Nowakowska, E. Wyrzykiewicz and B. Kedzia, Il Farmaco 57, 657–661 (2002).
Z. Nowakowska, Magn. Reson. Chem. 38, 382–383 (2000).
B.Z. Jovanovi´c, M.M. Vukovi´c, A.D. Marinkovi´c and J. Csan´adi, J. Mol. Struct. 482-483, 371-374 (1999).
National Committee for Clinical Laboratory Standard, NCCLS Document M7-A3, 13 (25), Willanova, PA., USA, 1993.
M. Cuendet, K. Hostettmann and O. Potterat, Helv. Chim. Acta 80, 1144-1152 (1997).