Synthesis and biological acitivities of N-alkyl derivatives of o-,m-, and p-nitro (E)-4-azachalcones and stereoselective photochemistry in solution, with theoretical calculations

KÜÇÜK, MURAT; YAYLI, Nurettin; YAŞAR, AHMET; ÜÇÜNCÜ, OSMAN; YAYLI, Nuran; AKYÜZ TURUMTAY, EMİNE; Alpay Karaoğlu, Şengül

Synthesis and biological acitivities of N-alkyl derivatives of o-,m-, and p-nitro (E)-4-azachalcones and stereoselective photochemistry in solution, with theoretical calculations

Nurettin YAYLI, (Karadeniz Teknik Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

Osman ÜÇÜNCÜ, (Karadeniz Teknik Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

Ahmet YAŞAR, (Karadeniz Teknik Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

Murat KÜÇÜK, (Karadeniz Teknik Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

Nuran YAYLI, (Karadeniz Teknik Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

EMİNE AKYÜZ TURUMTAY, (Karadeniz Teknik Üniversitesi, Fen Edebiyat Fakültesi, Biyoloji Bölümü, Trabzon, Türkiye)

ŞENGÜL ALPAY KARAOĞLU (Karadeniz Teknik Üniversitesi, Fen Edebiyat Fakültesi, Biyoloji Bölümü, Trabzon, Türkiye)

Turkish Journal of Chemistry

7 0

Yıl: 2006 Cilt: 30 Sayı: 4 Sayfa Aralığı: 505 - 514 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

Synthesis and biological acitivities of N-alkyl derivatives of o-,m-, and p-nitro (E)-4-azachalcones and stereoselective photochemistry in solution, with theoretical calculations

Öz:

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-pyridmium 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, $(1beta,2alpha)$-di-(3-nitrobenzoyl)-$(3beta,4alpha)$-di-(4-pyridinyl)cyclobutane (7), $(1beta,2alpha)$-di-(4-nitrobenzoyl)-$(3beta,4alpha)$-di-(4-pyridinyl)cyclobutane (8a), and $(1beta,2alpha)$-di-(4-nitrobenzoyl)-$(3beta,4alpha)$-di-(4-pyridinyl)cyclobutane (8b), stereoselectively. The monomeric compounds showed good antimicrobial activity against test micro-organisms. The most sensitive microorganisms 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 antipxidants Trolox and vitamin C, respectively. The possible dimerisation products of compounds 1-3 were calculated theoretically. Experimental and theoretical calculations showed that5-truxinic type dimer is the most stable isomer.

Anahtar Kelime:

Konular: Mühendislik, Kimya

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

1. J.B. Harborne, “The Flavonoids, Advances in Research”, Chapman & Hall, New York NY, 329-388, 1988.
2. J.P.J. Marais, D. Ferreira and D. Slade, Phytochemistry 66, 2145-2176 (2005).
3. Z. Nowakowska, E. Wyrzykiewicz and B. Kedzia, Il Farmaco 56, 325–329 (2001).
4. M.L. Edwards, D.M. Stemarick, J.S. Sabol, K.A. Diekema and R.J. Dinerstein, J. Med. Chem. 37, 4357-4362 (1994).
5. M. D’Auira and R. Racioppi, Tetrahedron 53, 17307-17316 (1997).
6. M. D’Auria, L. Emanuele, V. Esposito and R. Racioppi, Arkivoc (xi), 65-78 (2002).
7. M. D’Auria, Heterocycles, 54, 475-496 (2000).
8. M. D’Auria, L. Emanuele, G. Mauriello and R. Racioppi, J. Photochem. Photobiol. A, 134, 147-154 (2000).
9. N. Yaylı, A. Yaşar, O. Üçüncü, S. Ö. Sivrikaya, C. Güleç, M. Küçük and R. Abbasov, J. Photochem. Photobiol. A, 175, 291-298 (2005).
10. N. Yaylı, O. Üçüncü, A. Yaşar, Y. Gök, M. Küçük and S. Kolaylı, Turk. J. Chem., 28, 515-521 (2004).
11. N. Yaylı, O. Üçüncü, E. Aydın, Y. Gök, A. Yaşar, C. Baltacı, N. Yıldırım and M. Küçük, J. Photochem. Photobiol. A, 169, 229-234 (2005).
12. V. Seidel, F. Bailleul and P.G. Waterman, Phytochemistry 55, 439-446 (2000).
13. D.R. Katerere, A.I. Gray, A.R. Kennedy, R.J. Nash and R.D. Waigh, Phytochemistry 65, 433-438 (2004).
14. M. D’Auria and R. Racioppi, J. Photochem. Photobiol. A, 112, 145-148 (1998).
15. J. Durinda, L. Szucs, J. Kolena, A. Nagy, E. Misikova and J. Heger, Czech. Cesko-Slov. Farmac. 26, 140-149 (1977).
16. V.L. Aeppli, K. Bernuuer, F. Schneider, K. Strub, W.E. Oberhansli and K.H. Pfoertner, Helv. Chim. Acta 63, 630-644 (1980).
17. Z. Zhang, Y.W. Dong and G.W. Wang, Chem. Lett. 32, 966-967 (2003).
18. Z. Nowakowska, E. Wyrzykiewicz and B. Kedzia, Il Farmaco 57, 657–661 (2002).
19. Z. Nowakowska, Magn. Reson. Chem. 38, 382–383 (2000).
20. B.Z. Jovanovic, M.M. Vukovic, A.D. Marinkovic and J. Csanadi, J. Mol. Struct. 482-483, 371-374 (1999).
21. National Committee for Clinical Laboratory Standard, NCCLS Document M7-A3, 13 (25), Willanova, PA., USA, 1993.
22. M. Cuendet, K. Hostettmann and O. Potterat, Helv. Chim. Acta 80, 1144-1152 (1997).

APA	YAYLI N, ÜÇÜNCÜ O, YAŞAR A, KÜÇÜK M, YAYLI N, AKYÜZ TURUMTAY E, Alpay Karaoğlu Ş (2006). Synthesis and biological acitivities of N-alkyl derivatives of o-,m-, and p-nitro (E)-4-azachalcones and stereoselective photochemistry in solution, with theoretical calculations. , 505 - 514.
Chicago	YAYLI Nurettin,ÜÇÜNCÜ OSMAN,YAŞAR AHMET,KÜÇÜK MURAT,YAYLI Nuran,AKYÜZ TURUMTAY EMİNE,Alpay Karaoğlu Şengül Synthesis and biological acitivities of N-alkyl derivatives of o-,m-, and p-nitro (E)-4-azachalcones and stereoselective photochemistry in solution, with theoretical calculations. (2006): 505 - 514.
MLA	YAYLI Nurettin,ÜÇÜNCÜ OSMAN,YAŞAR AHMET,KÜÇÜK MURAT,YAYLI Nuran,AKYÜZ TURUMTAY EMİNE,Alpay Karaoğlu Şengül Synthesis and biological acitivities of N-alkyl derivatives of o-,m-, and p-nitro (E)-4-azachalcones and stereoselective photochemistry in solution, with theoretical calculations. , 2006, ss.505 - 514.
AMA	YAYLI N,ÜÇÜNCÜ O,YAŞAR A,KÜÇÜK M,YAYLI N,AKYÜZ TURUMTAY E,Alpay Karaoğlu Ş Synthesis and biological acitivities of N-alkyl derivatives of o-,m-, and p-nitro (E)-4-azachalcones and stereoselective photochemistry in solution, with theoretical calculations. . 2006; 505 - 514.
Vancouver	YAYLI N,ÜÇÜNCÜ O,YAŞAR A,KÜÇÜK M,YAYLI N,AKYÜZ TURUMTAY E,Alpay Karaoğlu Ş Synthesis and biological acitivities of N-alkyl derivatives of o-,m-, and p-nitro (E)-4-azachalcones and stereoselective photochemistry in solution, with theoretical calculations. . 2006; 505 - 514.
IEEE	YAYLI N,ÜÇÜNCÜ O,YAŞAR A,KÜÇÜK M,YAYLI N,AKYÜZ TURUMTAY E,Alpay Karaoğlu Ş "Synthesis and biological acitivities of N-alkyl derivatives of o-,m-, and p-nitro (E)-4-azachalcones and stereoselective photochemistry in solution, with theoretical calculations." , ss.505 - 514, 2006.
ISNAD	YAYLI, Nurettin vd. "Synthesis and biological acitivities of N-alkyl derivatives of o-,m-, and p-nitro (E)-4-azachalcones and stereoselective photochemistry in solution, with theoretical calculations". (2006), 505-514.

APA	YAYLI N, ÜÇÜNCÜ O, YAŞAR A, KÜÇÜK M, YAYLI N, AKYÜZ TURUMTAY E, Alpay Karaoğlu Ş (2006). Synthesis and biological acitivities of N-alkyl derivatives of o-,m-, and p-nitro (E)-4-azachalcones and stereoselective photochemistry in solution, with theoretical calculations. Turkish Journal of Chemistry, 30(4), 505 - 514.
Chicago	YAYLI Nurettin,ÜÇÜNCÜ OSMAN,YAŞAR AHMET,KÜÇÜK MURAT,YAYLI Nuran,AKYÜZ TURUMTAY EMİNE,Alpay Karaoğlu Şengül Synthesis and biological acitivities of N-alkyl derivatives of o-,m-, and p-nitro (E)-4-azachalcones and stereoselective photochemistry in solution, with theoretical calculations. Turkish Journal of Chemistry 30, no.4 (2006): 505 - 514.
MLA	YAYLI Nurettin,ÜÇÜNCÜ OSMAN,YAŞAR AHMET,KÜÇÜK MURAT,YAYLI Nuran,AKYÜZ TURUMTAY EMİNE,Alpay Karaoğlu Şengül Synthesis and biological acitivities of N-alkyl derivatives of o-,m-, and p-nitro (E)-4-azachalcones and stereoselective photochemistry in solution, with theoretical calculations. Turkish Journal of Chemistry, vol.30, no.4, 2006, ss.505 - 514.
AMA	YAYLI N,ÜÇÜNCÜ O,YAŞAR A,KÜÇÜK M,YAYLI N,AKYÜZ TURUMTAY E,Alpay Karaoğlu Ş Synthesis and biological acitivities of N-alkyl derivatives of o-,m-, and p-nitro (E)-4-azachalcones and stereoselective photochemistry in solution, with theoretical calculations. Turkish Journal of Chemistry. 2006; 30(4): 505 - 514.
Vancouver	YAYLI N,ÜÇÜNCÜ O,YAŞAR A,KÜÇÜK M,YAYLI N,AKYÜZ TURUMTAY E,Alpay Karaoğlu Ş Synthesis and biological acitivities of N-alkyl derivatives of o-,m-, and p-nitro (E)-4-azachalcones and stereoselective photochemistry in solution, with theoretical calculations. Turkish Journal of Chemistry. 2006; 30(4): 505 - 514.
IEEE	YAYLI N,ÜÇÜNCÜ O,YAŞAR A,KÜÇÜK M,YAYLI N,AKYÜZ TURUMTAY E,Alpay Karaoğlu Ş "Synthesis and biological acitivities of N-alkyl derivatives of o-,m-, and p-nitro (E)-4-azachalcones and stereoselective photochemistry in solution, with theoretical calculations." Turkish Journal of Chemistry, 30, ss.505 - 514, 2006.
ISNAD	YAYLI, Nurettin vd. "Synthesis and biological acitivities of N-alkyl derivatives of o-,m-, and p-nitro (E)-4-azachalcones and stereoselective photochemistry in solution, with theoretical calculations". Turkish Journal of Chemistry 30/4 (2006), 505-514.