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

Murat Turkyilmaz; Murat Dönmez; Murat Ates

Article Details

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

Authors:

Murat Turkyilmaz | Murat Dönmez | Murat Ates

Publisher:

Yildiz Technical University

Main Topics:

Chemical Engineering

Journal:

Journal of Sustainable Construction Materials and Technologies Vol.8 Issue 1, pp.27-34

Document Type:

Article

Publication Date:

3/2023

Document Language:

English

Document ID (Org No.):

2001287252

pISSN:

2458-973X

Keywords:

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-benzod imidazole 1 and 2,6-bischloromethylpyridine 2 were reacted to form 5,6-dimethyl-1- 6-5,6-dimethyl-1H-benzodimidazole-1-ilmethylpyridine-2-ilmethyl-1H-benzod 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 silverI 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.

 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-benzod imidazole 1 and 2,6-bischloromethylpyridine 2 were reacted to form 5,6-dimethyl-1- 6-5,6-dimethyl-1H-benzodimidazole-1-ilmethylpyridine-2-ilmethyl-1H-benzod 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 silverI 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.

 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-benzod imidazole 1 and 2,6-bischloromethylpyridine 2 were reacted to form 5,6-dimethyl-1- 6-5,6-dimethyl-1H-benzodimidazole-1-ilmethylpyridine-2-ilmethyl-1H-benzod 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 silverI 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.

 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-benzodimidazol 1 ve 2,6-bisklorometilpiridin 2 reaksiyona girerek 5,6-dimetil-1-6 oluşturdu. -5,6-dimetil-1H-benzodimidazol-1-ilmetilpiridin-2-ilmetil-1H-benzodimidazol 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 gümüşI 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.

Article Details

Authors: Murat Turkyilmaz | Murat Dönmez | Murat Ates

Publisher: Yildiz Technical University

Main Topics: Chemical Engineering

Journal: Journal of Sustainable Construction Materials and Technologies Vol.8 Issue 1, pp.27-34

Document Type: Article

Publication Date: 3/2023

Document Language: English

Document ID (Org No.): 2001287252

pISSN: 2458-973X

Issues

Authors:

Murat Turkyilmaz | Murat Dönmez | Murat Ates

Publisher:

Yildiz Technical University

Main Topics:

Chemical Engineering

Journal:

Journal of Sustainable Construction Materials and Technologies Vol.8 Issue 1, pp.27-34

Document Type:

Article

Publication Date:

3/2023

Document Language:

English

Document ID (Org No.):

2001287252

pISSN:

2458-973X