Synthesis of macrocyclization cyclophanes and their metal complexes, characterization and antimicrobial activity

Year 2023, , 27 - 34, 31.03.2023

Murat Turkyilmaz , Murat Dönmez , Murat Ates

https://doi.org/10.47481/jscmt.1253033

Abstract

Due to their chemical properties, cyclophane-type compounds constitute an interesting organic chemistry class. In the structure of all cyclic compounds, macrocyclization is the most
critical issue for high-efficiency synthesis. Especially with a small cyclophane structure, the
experimental steps are more complicated than with a prominent cyclophane structure. In
this manuscript, three different material groups were applied to synthesize silver cyclophane
compounds for smart drug properties. In the first material group, 5,6-dimetil-1H-benzo[d]
imidazole (1) and 2,6-bis(chloromethyl)pyridine (2) were reacted to form 5,6-dimethyl-1-
((6-((5,6-dimethyl-1H-benzo[d]imidazole-1-il)methyl)pyridine-2-il)methyl)-1H-benzo[d]
imidazole compound (3). In the second material group, ethyl 2-bromoacetate (4) reacted to
different nitrogen atoms of the cyclophane compound to form a symmetric carbene compound, which is water-soluble (5). In the third material group, the silver (I) and palladium
(II) metal complexes were synthesized due to the reaction with silver(I) oxide (6) and palladium (II) chloride (7). Antimicrobial activities of the carbene compounds and silver and
palladium complexes (5, 6, and 7) were investigated against bacteria and fungal in more detail.
Silver (I) complex (6) shows an antimicrobial agent when mixed with microorganisms, such
as Gram-positive, Gram-negative, and fungal, but this property has not been observed in the
palladium (II)-carbene complex (7).

Keywords

metal complex, carbene, cyclophane, antimikrobiyal aktivite

Supporting Institution

Trakya University

Project Number

TUBAP-2014-106

Thanks

This study received financial support from the Trakya University Research Fund (TUBAP-2014-106).

Synthesis of macrocyclization cyclophanes and their metal complexes, characterization and antimicrobial activity

Abstract

Siklofan tipi bileşikler, kimyasal özelliklerinden dolayı ilginç bir organik kimya sınıfı oluşturmaktadır. Tüm siklik bileşiklerin yapısında yüksek verimli sentez için makrosiklizasyon en kritik konudur. Özellikle küçük bir siklofan yapısı ile deneysel adımlar büyük bir siklofan yapısına göre daha zordur.
Bu yazıda, akıllı ilaç özellikleri için gümüş siklofan bileşiklerini sentezlemek üzere üç farklı malzeme grubu uygulanmıştır. Birinci malzeme grubunda 5,6-dimetil-1H-benzo[d]imidazol (1) ve 2,6-bis(klorometil)piridin (2) reaksiyona girerek 5,6-dimetil-1-((6) oluşturdu. -((5,6-dimetil-1H-benzo[d]imidazol-1-il)metil)piridin-2-il)metil)-1H-benzo[d]imidazol bileşik (3). İkinci malzeme grubunda etil 2-bromoasetat (4), suda çözünür (5) olan simetrik bir karben bileşiği oluşturmak üzere siklofan bileşiğinin farklı nitrojen atomları ile reaksiyona sokulmuştur. Üçüncü malzeme grubunda gümüş(I) oksit (6) ve paladyum (II) klorür (7) ile reaksiyona girerek gümüş (I) ve paladyum (II) metal kompleksleri sentezlendi.
Karben bileşikleri ile gümüş ve paladyum komplekslerinin (5, 6 ve 7) bakteri ve mantarlara karşı antimikrobiyal aktiviteleri daha detaylı olarak incelenmiştir. Gümüş (I) kompleksi (6), Gram-pozitif, Gram-negatif ve mantar gibi mikroorganizmalar ile karıştırıldığında antimikrobiyal madde gösterirken, bu özellik paladyum (II)-karben kompleksinde (7) gözlenmemiştir.

Keywords

carbene, cyclophane, metal complexe

Project Number

TUBAP-2014-106

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