Synthesis of Some Novel Isoxazolidine Derivatives via 1,3-Dipolar Cycloaddition and Their Biological Evaluation
Abstract
A series of novel substituted isoxazolidine derivatives were synthesized by 1,3-dipolar cycloaddition reaction. The structures of the synthesized compounds were characterized using spectroscopic methods. All the synthesized compounds were screened for their antibacterial activities against Gram-positive and Gram-negative bacteria and for their antifungal activities against a yeast strain. The results show that all the synthesized compounds displayed significant activity against S. epidermis, M. luteus, B. cereus, B. abortus and C. albicans when compared to standard drugs.
Keywords
References
- Zhu, J., Lines B.M., Ganton, M.D., Kerr, M.A. and Workentin, M.S., “Efficient synthesis of isoxazolidine tethered monolayer-protected gold nanoparticles (MPGNs) via 1,3-dipolar cycloadditions under high-pressure conditions”, J. Org. Chem., 73(3): 1099-1105, (2008).
- Karthikeyan, K., Perumal, P.T., Etti, S. and Shanmugam, G., “Diastereoselective syntheses of pyrazolyl via 1,3-dipolar cycloaddition”, Tetrahedron, 63(43): 10581-10586, (2007).
- Dondas, H.A., Cummins, J.E., Grigg, R. and Thornton, P.M., “X=Y–ZH Systems as potential 1,3-dipoles. Part 53: Sequential nucleophilic ring opening-1,3-dipolar cycloaddition reactions of Z-oxime anions with aziridines and dipolarophiles”, Tetrahedron, 57(37): 7951-7964, (2001).
- Casuscelli, F., Chiaccho, U., Rescifina, A., Romeo, R., Romeo, G., Tommasini, S. and Uccella, N., “Ring-opening of isoxazolidine nucleus: Competitive formation of α,β-enones and tetrahydro-1,3-oxazines”, Tetrahedron, 51(10): 2979-2990, (1995).
- Damodiran, M., Sivakumar, P.M., Senthil Kumar, R., Muralidharan, D., Kumar, B.V.N.P., Doble, M. and Perumal, P.T., “Antibacterial activity, quantitative structure–activity relationship and diastereoselective synthesis of ısoxazolidine derivatives via 1,3-dipolar cycloaddition of D-glucose derived nitrone with olefin”, Chem. Biol. Drug. Des., 74(5): 494-506, (2009).
- Yin, Z., Zhang, J., Wu, J., Liu, C., Sioson, K., Devany, M., Hu, C. and Zheng, S., “Double hetero-Michael addition of N substituted hydroxylamines to quinone monoketals: synthesis of bridged isoxazolidines”, Org. Lett.,15(4): 3534-3537, (2013).
- Ali, A.S., Khan, J.H. and Wazeer, M.I.M., “The regiochemistry and stereochemistry of 1,3-dipolar cycloaddition of cyclic nitrones”, Tetrahedron, 44(18): 5911-5920, (1998).
- Jäger, V. and Müller, I., “Synthesis of amino sugars via isoxazolines: Nitrile oxide-furan adducts as key intermediates in the isoxazoline route towards novel amino sugar derivatives”, Tetrahedron, 41(17): 3519-3528, (1985).
Details
Primary Language
English
Subjects
Engineering
Journal Section
Research Article
Authors
Volkan Yanmaz
This is me
Gazi University
Türkiye
Ali Dıslı
Gazi University
Türkiye
Serkan Yavuz
Gazi University
Türkiye
Hatice Ogutcu
Ahi Evran University
Türkiye
Gulay Dılek
BÜLENT ECEVİT ÜNİVERSİTESİ
Türkiye
Publication Date
March 1, 2019
Submission Date
January 24, 2018
Acceptance Date
October 5, 2018
Published in Issue
Year 2019 Volume: 32 Number: 1