4-Hidroksi Salisilaldehit ile İzoforondiaminin schiff bazlarının sentezi, karakterizasyonu, biyolojik aktiviteleri ve kuramsal çalışmaları
Yükleniyor...
Dosyalar
Tarih
2023
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Bursa Teknik Üniversitesi, Lisansüstü Eğitim Enstitüsü
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
Günümüzde schiff bazları kolay sentezlenebilmesinden ve kimya, biyoloji, ilaç kimyası gibi birçok alanda kullanımından dolayı önemli bir yere sahiptir. Schiff bazları, herhangi bir birincil amin, belirli koşullar altında bir aldehit veya bir keton ile reaksiyona girdiğinde oluşur. Schiff bazlarının antibakteriyel, antifungal, antikanser, antioksidan, antienflamatuar, antimalaryal, antiviral aktivite gibi uygulama alanlarında etkili oluğu bilinmektedir. Bu durum göz önünde bulundurulduğunda yeni schiff bazlarının sentezlenmesi, deneysel ve teorik olarak karakterizasyonunun gerçekleştirilmesi, deneysel ve teorik olarak antibakteriyel aktivitelerinin incelenmesi düşünülmüştür. Bu çalışmada 4 hidroksi salisilaldehit ve izoforondiamin (IPDA) 1:1 ve 2:1 oranda kullanılarak ((((5-amino,1,3,3trimetilsikloheksil)metil)imino)metil)benzen-1,3-diol (L1) ve ((((2,4-dihidroksibenziliden)amino)1,3,3trimetilsikloheksil)metil)imino)metil)benzen-1,3-diol (L2) ligandları sentezlenmiştir. Sentezlenen ligandlar FT-IR, Uv-Gör., NMR spektroskopik yöntemleri ve elementel analiz kullanılarak karakterize edilmiştir. Sentezlenen ligandların optimizasyonları, bağ açıları, bağ uzunlukları, HOMO-LUMO, bant aralığı enerjileri, MEP haritaları, bazı fizikokimyasal özellikleri, FT-IR, Uv-Gör., NMR gibi spektroskopik verileri gaussian paket programı yardımıyla DFT/B3LYP metodu 6-311++G(d,p) taban kümesi kullanılarak hesaplanmıştır. L2 ligandının karakterizasyonunu desteklenmesi için elementel analiz yapılarak yapısı aydınlatılmıştır. Sentezlenen ligandların E.coli ve S.aureus bakterilerine karşı antibakteriyel özellikleri disk difüzyon metodu kullanılarak incelenmiştir. Sentezlenen ligandların teorik olarak E.coli ve S.aureus bakterilerine karşı antibakteriyel özellikleri moleküler docking yöntemi kullanılarak autodock vina programı ile hesaplanmıştır. Sentezlenen ligandların FT-IR spektroskopisine bakıldığında 4 hidroksi salisilaldehitte bulunan karbonil (C=O) bandının kaybolarak yerini schiff bazında bulunan imin (C=N) bandının aldığı gözlemlenmiştir. 3000 cm-1 dalga boyunun üstündeki bölgede bulunan bant aromatik halkayı ve 3000 cm-1 dalga boyunun altındaki bölgede bulunan bant alifatik grupları göstermektedir. Sentezlenen ligandların 1H-NMR spektroskopisinde 8-8.50 ppm aralığında ve 13C-NMR spektroskopisinde 160-170 ppm aralığındaki pikler imin (-CH=N-) grubunun göstergesidir. Sentezlenen ligandların bakterilerin bulunduğu agar üzerinde herhangi bir alan oluşturmamaları bu ligandların antibakteriyel aktivitesinin zayıf olduğunu göstermektedir.
Nowadays, Schiff bases have an important place due to their easy synthesis and their use in many fields such as chemistry, biology, pharmaceutical chemistry. Schiff bases are formed when any primary amine reacts with an aldehyde or a ketone under certain conditions. It is known that Schiff bases are effective in application areas such as antibacterial, antifungal, anticancer, antioxidant, anti-inflammatory, antimalarial, antiviral activity. Considering this situation, synthesizing new schiff bases, performing their experimental and theoretical characterization, and examining their experimental and theoretical antibacterial activities were considered. In this study, 4 hydroxy salicylaldehyde and isophorondiamine (IPDA) were used in 1:1, 2:1 ratios to synthesize (((((5-amino1,3,3trimethylcyclohexyl)methyl)imino)methyl) benzene-1,3diol (L1) and ((((2, 4-dihydroxybenzylidene)amino)1,3,3trimethylcyclohexyl)methylimino)methyl)benzene-1,3-diol (L2) ligands. The synthesized ligands were characterized using FT-IR, Uv-Vis., NMR spectroscopic methods and elemental analysis. Optimization of synthesized ligands, bond angles, bond lengths, HOMO-LUMO, band gap energies, MEP maps, some physicochemical properties and spectroscopic data such as NMR, elemental analysis FT-IR and Uv-Vis. were calculated using the DFT/B3LYP method 6-311++G(d,p) base set with the help of the gaussian package program. To support the characterization of the L2 ligand, its structure was elucidated by elemental analysis. Antibacterial properties of the synthesized ligands against E.coli and S.aureus bacteria were investigated using disk diffusion method. The antibacterial properties of the synthesized ligands against E.coli and S.aureus bacteria were calculated with the autodock vina program using the molecular docking method. When the FT-IR spectroscopy of the synthesized ligands was examined, it was observed that the carbonyl (C=O) band in 4 hydroxy salicylaldehyde disappeared and replaced by the imine (C=N) band on the Schiff basis. The band in the region above 3000 cm-1 wavelength indicates the aromatic ring and the band in the region below 3000 cm-1 wavelength indicates aliphatic groups. The peaks of the synthesized ligands in the range of 8-8.50 ppm in 1H-NMR spectroscopy and in the range of 160-170 ppm in 13C-NMR spectroscopy are indicative of the imine (-CH=N-) group. The fact that the synthesized ligands did not form any area on the agar with bacteria indicates that these ligands do not have antibacterial activity.
Nowadays, Schiff bases have an important place due to their easy synthesis and their use in many fields such as chemistry, biology, pharmaceutical chemistry. Schiff bases are formed when any primary amine reacts with an aldehyde or a ketone under certain conditions. It is known that Schiff bases are effective in application areas such as antibacterial, antifungal, anticancer, antioxidant, anti-inflammatory, antimalarial, antiviral activity. Considering this situation, synthesizing new schiff bases, performing their experimental and theoretical characterization, and examining their experimental and theoretical antibacterial activities were considered. In this study, 4 hydroxy salicylaldehyde and isophorondiamine (IPDA) were used in 1:1, 2:1 ratios to synthesize (((((5-amino1,3,3trimethylcyclohexyl)methyl)imino)methyl) benzene-1,3diol (L1) and ((((2, 4-dihydroxybenzylidene)amino)1,3,3trimethylcyclohexyl)methylimino)methyl)benzene-1,3-diol (L2) ligands. The synthesized ligands were characterized using FT-IR, Uv-Vis., NMR spectroscopic methods and elemental analysis. Optimization of synthesized ligands, bond angles, bond lengths, HOMO-LUMO, band gap energies, MEP maps, some physicochemical properties and spectroscopic data such as NMR, elemental analysis FT-IR and Uv-Vis. were calculated using the DFT/B3LYP method 6-311++G(d,p) base set with the help of the gaussian package program. To support the characterization of the L2 ligand, its structure was elucidated by elemental analysis. Antibacterial properties of the synthesized ligands against E.coli and S.aureus bacteria were investigated using disk diffusion method. The antibacterial properties of the synthesized ligands against E.coli and S.aureus bacteria were calculated with the autodock vina program using the molecular docking method. When the FT-IR spectroscopy of the synthesized ligands was examined, it was observed that the carbonyl (C=O) band in 4 hydroxy salicylaldehyde disappeared and replaced by the imine (C=N) band on the Schiff basis. The band in the region above 3000 cm-1 wavelength indicates the aromatic ring and the band in the region below 3000 cm-1 wavelength indicates aliphatic groups. The peaks of the synthesized ligands in the range of 8-8.50 ppm in 1H-NMR spectroscopy and in the range of 160-170 ppm in 13C-NMR spectroscopy are indicative of the imine (-CH=N-) group. The fact that the synthesized ligands did not form any area on the agar with bacteria indicates that these ligands do not have antibacterial activity.
Açıklama
Anahtar Kelimeler
Kimya, Chemistry
