Bazı aldehit türevlerinin İzoforondiamin (IPDA) ile oluşturdukları Schiff bazlarının sentezi, karakterizasyonu, biyolojik aktiviteleri ve kuramsal çalışmaları
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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
Schiff bazları antibakteriyel aktiviteleri nedeniyle biyokimya alanında önemli bileşiklerdir. Schiff bazları aldehit veya ketonların birincil amin ile kondenzasyonu ile oluşurlar. Bu çalışmada 3-4 dihidroksisalisilaldehit, 5-bromosalisilaldehit ve vanilin aldehitlerinin izoforondiamin (IPDA) ile asidik ortamda reaksiyonu sonucu üç farklı L1((((5-amino-1,3,3-trimetilsiklohekzil)metil)imino)metil)benzen-1,2,3-triol), L2 ((((5-amino-1,3,3-trimetilsiklohekzil)methil)imino)methil)-4-bromofenol) ve L3 ((((5-amino-1,3,3-trimethilsiklohekzil)methil)imino)metil)-2 metoksifenol) Schiff bazı sentezlenmiştir. Sentezlenen ligandların karakterizasyonu deneysel ve teorik olarak FT-IR, UV-Gör. ve NMR spektroskopik yöntemleri kullanılarak gerçekleştirilmiştir. Sentezlenen ligandların teorik FT-IR, NMR, UV-Gör. spektrumları, HOMO-LUMO, bant aralığı enerjileri, MEP haritaları ve bazı fizikokimyasal özellikleri Gaussian paket programı ile DFT-B3LYP metodu ve 6-311++G(d,p) taban kümesi kullanılarak hesaplanmıştır. Aynı zamanda bu ligandların S. aureus ve E. coli bakterilerine karşı antibakteriyel aktivitesi deneysel olarak disk difüzyon metodu, teorik olarak moleküler docking metodu ile Autodock Vina programı kullanılarak incelenmiştir. FT-IR spektroskopisinde giriş maddeleri olan aldehitlerde bulunan 1650-1700 cm-1 bölgesinde bant gösteren v(C=O) gerilme titreşimlerinin yerini Schiff bazlarında bulunan ve 1600-1650 cm-1 bölgesinde bant gösteren v(C=N) gerilme titreşimlerine bırakması, 3000 cm-1 üstündeki aromatik v(C-H) gerilme titreşimlerinin ve 3000 cm-1 altındaki alifatik v(C-H) gerilme titreşimlerinin oluşması bileşiklerin sentezlediğinin kanıtlarındandır. 1H NMR spektrumunda 8-9 ppm ve 13C NMR spektrumda 160-170 ppm arasında gözlemlenen bant C=N grubunu temsil etmektedir. Deneysel ve teorik olarak elde edilen spektroskopik verilerin birbirleri ile uyumlu olduğu belirlenmiştir. Sentezlenen ligandların S. aureus ve E. coli bakterilerine karşı antibakteriyel aktiviteleri incelenmiştir. L3 ligandının bakterilerin bulunduğu agar üzerinde bölge oluşturduğu ve bu bakterilere karşı antibakteriyel etkinlik gösterdiği gözlemlenmiştir.
Schiff bases are important compounds in the field of biochemistry due to their antibacterial activity. Schiff bases are formed by the condensation of aldehydes or ketones with a primary amine. In this study, three different L1(4-((((5-amino-1,3,3-trimethylcyclohexyl)methyl)imino)methyl)benzene-1,2,3-triol), L2(2-((((5-amino 1,3,3-trimethylcyclohexyl)methyl)imino)methyl)-4-bromophenol), L3(4-((((5-amino-1,3,3-trimethylcyclohexyl)methyl)imino)methyl)-2-methoxyphenol) Schiff bases were synthesized as a result of the reaction of 3-4 dihydroxysalicylaldehyde, 5-bromosalicylaldehyde and vanillin aldehydes with isophorondiamine (IPDA) in acidic medium. The characterization of the synthesized ligands were carried out experimentally and theoretically using FT-IR, UV-VIS and NMR spectroscopic methods. Theoretical FT-IR, NMR, UV-VIS spectra, HOMO-LUMO, band gap energies, MEP maps and some physicochemical properties of the synthesized ligands were calculated with Gaussian package program using DFT-B3LYP method and 6-311++G(d,p) base set. At the same time, the antibacterial activity of these ligands against S. aureus and E. coli bacteria was investigated using the disk diffusion method. Antibacterial activities were theoretically investigated by molecular docking method using Autodock Vina program. In FT-IR spectroscopy, the v(C=O) stretching vibrations, which show banding in the 1650-1700 cm-1 region in the aldehydes, which are the input materials, are replaced by the v(C=N) stretching vibrations in the Schiff bases, which show a band in the 1600-1650 cm-1 region, the formation of aromatic v(C-H) stretching vibrations above 3000 cm-1 and aliphatic v(C-H) stretching vibrations below 3000 cm-1 are the proofs that the compounds synthesized. The band observed in the 8-9 ppm region in the 1H NMR spectrum represents the C=N group. It was determined that the spectroscopic data obtained experimentally and theoretically were compatible with each other. Antibacterial activities of synthesized ligands against S. aureus and E. coli bacteria were investigated. It was observed that the L3 ligand formed a region on the agar with bacteria and showed antibacterial activity against these bacteria.
Schiff bases are important compounds in the field of biochemistry due to their antibacterial activity. Schiff bases are formed by the condensation of aldehydes or ketones with a primary amine. In this study, three different L1(4-((((5-amino-1,3,3-trimethylcyclohexyl)methyl)imino)methyl)benzene-1,2,3-triol), L2(2-((((5-amino 1,3,3-trimethylcyclohexyl)methyl)imino)methyl)-4-bromophenol), L3(4-((((5-amino-1,3,3-trimethylcyclohexyl)methyl)imino)methyl)-2-methoxyphenol) Schiff bases were synthesized as a result of the reaction of 3-4 dihydroxysalicylaldehyde, 5-bromosalicylaldehyde and vanillin aldehydes with isophorondiamine (IPDA) in acidic medium. The characterization of the synthesized ligands were carried out experimentally and theoretically using FT-IR, UV-VIS and NMR spectroscopic methods. Theoretical FT-IR, NMR, UV-VIS spectra, HOMO-LUMO, band gap energies, MEP maps and some physicochemical properties of the synthesized ligands were calculated with Gaussian package program using DFT-B3LYP method and 6-311++G(d,p) base set. At the same time, the antibacterial activity of these ligands against S. aureus and E. coli bacteria was investigated using the disk diffusion method. Antibacterial activities were theoretically investigated by molecular docking method using Autodock Vina program. In FT-IR spectroscopy, the v(C=O) stretching vibrations, which show banding in the 1650-1700 cm-1 region in the aldehydes, which are the input materials, are replaced by the v(C=N) stretching vibrations in the Schiff bases, which show a band in the 1600-1650 cm-1 region, the formation of aromatic v(C-H) stretching vibrations above 3000 cm-1 and aliphatic v(C-H) stretching vibrations below 3000 cm-1 are the proofs that the compounds synthesized. The band observed in the 8-9 ppm region in the 1H NMR spectrum represents the C=N group. It was determined that the spectroscopic data obtained experimentally and theoretically were compatible with each other. Antibacterial activities of synthesized ligands against S. aureus and E. coli bacteria were investigated. It was observed that the L3 ligand formed a region on the agar with bacteria and showed antibacterial activity against these bacteria.
Açıklama
Anahtar Kelimeler
Kimya, Chemistry
