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Journals / Turkish Journal of Chemistry / 2006 / Cilt: 30 - Sayı: 4

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

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
Pages
505–514
Publication Date
2006-04-01
DOI
—
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Experimental and theoretical calculations showed that d-truxinic type dimer is the most stable isomer.

📌 3 Key Takeaways

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Objective & Hypothesis: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.
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Key Findings & Data:The monomers also showed high antioxidant activity, while the dimerisation products 7-8a,b were less active.
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Conclusion & Impact:Experimental and theoretical calculations showed that d-truxinic type dimer is the most stable isomer.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Nitro-(E)-4-azachalcones · nitro-(E)-N-decyl-4-azachalconium bromide · photodimerisation

Abstract

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.

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.

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Cite This Article

YAYLI, N., ÜÇÜNCÜ, O., YAŞAR, A., KÜÇÜK, M., YAYLI, N., AKYÜZ, E., KARAOĞLU, Ş. A. (2006). 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. Turkish Journal of Chemistry, Cilt: 30 - Sayı: 4, 505–514. https://ajindex.com/articles/185414

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