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

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

Makale detayları

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

Yazarlar:

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

Yayıncı:

TUBITAK

Ana Başlıklar:

Uygulamalı fizik

Dergi:

Turkish Journal of Chemistry 2006 Vol.30 Issue 4, pp.505-514

Belge Tipi:

Makale

Yayın Tarihi:

3/2006

Belge Dili:

İngilizce

Document ID (Org No.):

2000728875

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

Özet:

 

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.

 

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.

Makale detayları

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

Yazarlar: Nurettin YAYLI | Osman ÜÇÜNCÜ | Ahmet YAŞAR | Murat KÜÇÜK | Nuran YAYLI | Emine AKYÜZ | Şengül ALPAY KARAOĞLU

Yayıncı: TUBITAK

Ana Başlıklar: Uygulamalı fizik

Dergi: Turkish Journal of Chemistry 2006 Vol.30 Issue 4, pp.505-514

Belge Tipi: Makale

Yayın Tarihi: 3/2006

Belge Dili: İngilizce

Document ID (Org No.): 2000728875

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

Sayı

Yazarlar:

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

Yayıncı:

TUBITAK

Ana Başlıklar:

Uygulamalı fizik

Dergi:

Turkish Journal of Chemistry 2006 Vol.30 Issue 4, pp.505-514

Belge Tipi:

Makale

Yayın Tarihi:

3/2006

Belge Dili:

İngilizce

Document ID (Org No.):

2000728875

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527