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

Öz

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.

Anahtar Kelimeler

• carbene
• cyclophane
• metal complexe

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

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

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