Antibakteriyel Özelliğe Sahip Aminoglioksimlerin Sentezi ve Özelliklerinin İncelenmesi

Yıl 2021, Cilt: 21 Sayı: 4, 792 - 799, 31.08.2021

Önder Alıcı , Şule Kökten İbrahim Karataş , Erdoğan Güneş

https://doi.org/10.35414/akufemubid.932021

Öz

Bu çalışmada önce difenileterin kloroasetilklorür ile AlCl3 katalizörlüğündeki reaksiyonundan 4-kloroasetildifenileter sentezlenmiştir. Sonra bunun nitrosolama metoduyla isonitroso-4-asetildifenileteri ve hidroksilaminhidroklorür ile asidik ortamdaki reaksiyonundan 4-fenoksifenilkloroglioksimi elde edildi. Daha sonra bu anti-fenoksifenilkloroglioksimin 2-amino-4-feniltiyazol ve 2-fluorenamin ile reaksiyonundan orijinal olarak sübstitüe-aminogliksim türevleri sentezlendi. Elde edilen bileşiklerin yapıları FT-IR ve 1H-NMR teknikleri kullanılarak aydınlatıldı. Ayrıca sentezlenen iki başlangıç maddesi, sentezlenen sübstitüe-aminoglioksim türevleri ve iki amin bileşiğinin, Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 15442, metisilin duyarlı Staphylococcus aureus ATCC 25923 (MSSA), Klebsiella pneumoniae ATCC 70603, Salmonella enteritidis ATCC 13076 ve Sarcina lutea ATCC 9341 suşlarına karşı anti-bakteriyel özellikleri araştırıldı.

Anahtar Kelimeler

4-Fenoksifenilkloroglioksim, Sübstitüe-aminoglioksim, Anti-bakteriyel özellik, Organik Sentez

Destekleyen Kurum

Selçuk Üniversitesi

Proje Numarası

14201012

Teşekkür

Selçuk Üniversitesi Bilimsel Araştırma Projeleri Koordinatörlüğü

Synthesis of Aminoglioximes with Antibacterial Properties and Investigation of Properties

Öz

In this study, firstly 4-chloroacetyldiphenylether was synthesized from the reaction of diphenylether with chloroacetylchloride at AlCl3 catalysis. Then, 4-phenoxyphenyl-chloroglyoxime was obtained from reaction of isonitroso-4-acetyldiphenylether and hydroxylamine hydrochloride. Subsequently, substituted-amino glyoxime derivatives were originally synthesized from the reaction of this phenoxyphenylchloroglyoxime with 2-amino-4-phenylthiazole and 2-fluorenamine. The structures of the obtained compounds were tried to be elucidated using FT-IR and 1H-NMR techniques. In addition, Anti-bacterial properties of two starting materials synthesized, substituted-aminoglioxime derivatives synthesized and two amine compounds were investigated against the strains of Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 15442, methicillin sensitive Staphylococcus aureus ATCC 25923 (MSSA), Klebsiella pneumoniae ATCC 70603, Salmonella enteritidis ATCC 13076 and Sarcina lutea ATCC 9341.

Anahtar Kelimeler

4-Phenoxyphenylchloroglyoxime, Substituted-amino glyoxim, Anti-bacterial property, Organic Synthesis

Proje Numarası

14201012

Kaynakça

• Akiba, K. and Freisher, H., 1982. The Role of the Solvent in Equilibrum and Kinetic Aspect of Metal Chelate Extractions. Analytica Chimica Acta, 136, 329-337.
• Arda, M., 2000. Temel Mikrobiyoloji. Medisan Yayınevi, No: 46, 2. Baskı, Ankara, 1-80.
• Balcı, M., 2004. Nükleer Manyetik Spektroskopisi. ODTÜ Yayıncılık, 452, Ankara, 10-50.
• Bozdağ, O, Gümüşel B, Demirdamar R, Büyükbingöl E, Rolland, Y, Ertan R., 1998. Synthesis of some novel oxime ether derivatives and their activity in the ‘behavioral despair test’, European Journal of Medicinal Chemistry, 33, 133-141.
• Burakevich, J.V., Lore, A.M., ve Volpp, G.P., 1971. Phenylglyoxime separation, characterization, and structure of three ısomers, The Journal of Organic Chemistry, 36, 1-4.
• Cavallini, G., Massarani, E., Nardi, D., Mauri, L., Tenconi, F., Pacchiano, F., and Mantegazza, P., 1963. “Antibacterial Agents. Some New Halomethyl Aryl Ketones” Journal of Medicinal Chemistry, 6(5), 573–578.
• Chakravorty, A., 1974. Structural chemistry of transition metal complexes of oximes, Coordination Chemistry Reviews, 13 (1), 1-46.
• Coşkun, A. and Yılmaz, F., 2008. Synthesis and chracterization of 4-(alkylaminoisonitrosoacetyl)diphenyl ether and some of their metal Complexes, Turkish Journal of Chemistry, 32, 305-312.
• Dimmock, J.R., Sidhu, K.K., Chen, M., Li, J, Quail, J.W., Allen, T.M, ve Kao, G.Y., 1994. Synthesis and Cytotoxic Evaluation of Some Cyclic Arylidene Ketones and Related Oximes, Oxime Esters, and Analogs, Journal of Pharmaceutical Sciences, 83(6), 852–858.
• Gök, Y., 1981. Yeni α-Dioksim sentezleri, geometrik izomerleri ve bazı metallerle kompleks formasyonlarının incelenmesi, Doktora Tezi, Karadeniz Teknik Üniversitesi Fen Bilimleri Enstitüsü, Trabzon, 110.
• Gül, A., and Bekaroğlu, O., 1983. Syntheses of NN'-bis(4'-benzo[15-crown-5])diaminoglyoxime and its complexes with Copper(II), Nickel(II), Cobalt(II), Cobalt(III), Palladium(II), Platinum(II), and Uranyl(VI), Journal of The Chemical Society-dalton Transactions, 12, 2537-2541.
• Kara, A., 1995. Çeşitli oksimlerin sentezi ve özelliklerinin incelenmesi, Yüksek Lisans Tezi, Uludağ Üniversitesi Fen Bilimleri Enstitüsü, Bursa, 68.
• Karipcin, F., Arabalı, F. and Karataş, I., 2006. Synthesis and chracterization of 4-aryl- aminobiphenylglyoximes and their complexes, Journal of the Chilean Chemical Society, 51(3), 982-985.
• Keeney, M.E. ve Asare, K.O., 1984. Transition Metal Hydroxyoxime Complexes, Coordination Chemistry Reviews, 59, 141-201.
• Kleinspehn, G.G., Jung, J.A. and Studniaez, S.A., 1967. The Chemical Shift of the Hydroxyl Proton of Oxime in Dimethyl Sulfoxide, The Journal of Organic Chemistry, 32(2), 460-462.
• Kurtoğlu, M. ve Serin, S., 2006. Oksimler: Sentezi, Reaksiyonları ve Metal Kompleksleri, KSÜ-Fen ve Mühendislik Dergisi, 9(2), 25-32, Kahramanmaraş.
• Lecterc, G., Mann, A. and Schwartz, J., 1980. Synthesis and adrenergic bloking activity of new aliphatic oxime ethers, Journal of Medicinal Chemistry, 23(6), 620-624.
• Lecterc, G., Mann, A., Wermuth, C.G., Bieth, N. and Schwartz, J., 1977. Synthesis and adrenergic bloking activity of a novel class aromatic oxime ethers, Journal of Medicinal Chemistry, 20(12), 1657-1662.
• Massolini G, Kitsos M, Gandini C., Caccialanza G, 1989. Fungicidal activity of a series of phenyl pyridyl ketoximes and their O‐acetyl derivatives, Pesticide Science, 26, 209-214.
• Massolini G, Carmellino ML, Baruffini A, 1996. Fungicidal activity of arylfuryl ketoximes, Farmaco (Societa Chimica Italiana: 1989), 51(4), 287-292.
• Mohammed, A.H. ve Nagendrappa, G., 2003. A remarkably simple α-oximation of ketones to 1,2-dione monooximes using the chlorotrimethylsilane–isoamyl nitrite combination, Tetrahedron Letters, 44 (13), 2753-2755.
• Özdamar, H.N., Alıcı, Ö. ve Karataş, İ.,2015. New amino-keto oxime derivatives: Synthesis and Characterization, Journal of Selcuk University Natural and Applied Science, 4(4), 1-6, Konya.
• Patai, S., 1970. The chemistry of Carbon-Nitrogen double bond, 360, Interscience Publisher, London, 1-100.
• Purtaş, F., 2006. Suda çözünebilir yeni vic-dioksim ligandı ve bazı metal Komplekslerinin Sentezi, Yüksek Lisans Tezi, Kahramanmaraş Sütçü İmam Üniversitesi Fen Bilimleri Enstitüsü, Kahramanmaraş, 83.
• Silverstein, R.M., Bassler, G.C. ve Morrill, T.C., 1974. Spectrometric identification of organic compounds, John Wiley, 159-229.
• Singh, R.B., Garg, B.S. ve Singh, R.P., 1979. Oximes as spectrophotometric reagents-a review. Talanta, 26(6), 425–444.
• Smith, P.A.S., 1966. The Chemistry of Open-chain Organic Nitrogen Compounds: Derivatives of oxidized nitrogen: hydrazines to nitrates, V.2, New York, 28-68.
• Taş E., Ulusoy M. ve Güler M., 2004. Synthesis, characterization and redox properties of a new vic-dioxime and its transition metal complexes, Transition Metal Chemistry, 29, 180–184.
• Yılmaz, F., 2007. Fenoksifenilglioksim ve bazı geçiş metal komplekslerinin sentezi, Yüksek Lisans Tezi, Selçuk Üniversitesi Fen Bilimleri Enstitüsü, Konya, 89.
• Zengin, G., Uysal, A., Güneş, E., Aktümsek, A., 2014. Survey of phytochemical composition and biological effects of three extracts from a wild plant. A potential source for functional food ıngredients and drug formulations. PLOS ONE, 9(11): 1-13.