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.
📌 3 Key Takeaways
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Objective & Hypothesis:A series of novel substituted isoxazolidine derivatives were synthesized by 1,3-dipolar cycloaddition reaction.
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Key Findings & Data:The structures of the synthesized compounds were characterized using spectroscopic methods.
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Conclusion & Impact: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.
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.
Yanmaz, V., Dıslı, A., Yavuz, S., Ogutcu, H., Dılek, G. (2019). Synthesis of Some Novel Isoxazolidine Derivatives via 1,3-Dipolar Cycloaddition and Their Biological Evaluation. Gazi University Journal of Science, Volume: 32 Issue: 1. https://ajindex.com/articles/1269201
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).
Merino, P., Franco, S., Merchan, F.L. and Tejero, T., “Asymmetric synthesis of an isoxazolidine nucleoside analog of thymine polyoxin C”, Tetrahedron Lett., 39(35): 6411-6414, (1988).
Nora, G.P., Miller, M.J. and Möllmann, U., “The synthesis and in vitro testing of structurally novel antibiotics derived from acylnitroso Diels–Alder adducts”, Bioorg. Med. Chem. Lett., 16(15): 3966-3970, (2006).
Litvinovskaya, R.P., Koval, N.V. and Khripach, V.A., “Synthesis of modified vitamin D precursors”, Chem. Hetero. Comp., 36(2): 190-194, (2000).
Hanselmann, R., Zhou, J., Ma, P. and Confalone, P.N., “Synthesis of cyclic and acyclic β-amino acids via chelation-controlled 1,3-dipolar cycloaddition”, J. Org. Chem., 68(22): 8739-8741, (2003).
Chiacchio, U., Balestrieri, E., Macchi, B., Iannazzo, D., Piperino, A., Rescifina, A., Romeo, R., Saglimbeni, M., Sciortino, M.T., Valveri, V., Mastino, A. and Romeo, G., “Synthesis of phosphonated carbocyclic 2’-oxa-3’-aza-nucleosides: Novel inhibitors of reverse transcriptase”, J. Med. Chem., 48(5): 1389-1394, (2005).
Palmer, G.C., Ordy, M.J., Simmons. R.D., Strand, J.C., Radov, L.A., Mullen, G.B., Kinsolving, C.R., St Giorgiev, V., Mitchell, J.T. and Allen, S.D., “Selection of orally active antifungal agents from 3,5-substituted isoxazolidine derivatives based on acute efficacy-safety profiles”, Antimicrob. Agents Chemother., 33(6):895-905, (1989).
Kumar, K.R.R., Mallesha, H. and Basappa Rangappa, K.S., “Synthesis of novel isoxazolidine derivatives and studies for their antifungal properties”, Eur. J. Med. Chem., 38(6): 613-619, (2003).
Zhao, C. and Casida, J.E., “Insect γ-aminobutyric acid receptors and isoxazoline insecticides: Toxicological profiles relative to the binding sites of [3H]fluralaner, [3H]-4′-ethynyl-4-n-propylbicycloorthobenzoate, and [3H]avermectin”, J. Agric. Food. Chem., 62(5): 1019-1024, (2014).
Rakesh, D.S., Lee, R.B., Tangallapally, R.P. and Lee, R.E., “Synthesis, optimization and structure–activity relationships of 3,5-disubstituted isoxazolines as new anti-tuberculosis agents”, Eur. J. Med. Chem., 44(2): 460-472, (2009).
Habeeb, A.G., Rao, P.P.N. and Knaus, E.E., “Design and synthesis of 4,5-diphenyl-4-isoxazolines: Novel inhibitors of cyclooxygenase-2 with analgesic and antiinflammatory activity”, J. Med. Chem., 44(18): 2921-2927, (2001).
Mondal, P., Jana, S., Balaji, A., Ramakrishna, R. and Kanthal, L.K,. “Synthesis of some new isoxazoline derivatives of chalconised indoline 2-one as a potential analgesic, antibacterial and anthelmintic agents”, J. Young Pharm., 4(1): 38-41, (2012).
Pinto, D.J.P., Smallheer, J.M., Cheney, D.L., Knabb, R.M. and Wexler, R.R., “Factor Xa inhibitors: Next-generation antithrombotic agents”, J. Med. Chem., 53(17): 6243-6274, (2010).
Giofrè, S.V., Romeo, R., Carnovale, C., Mancuso, R., Cirmi, S., Navarra, M., Garozzo, A. and Chiacchio, M.A., “Synthesis and biological properties of 5-(1h-1,2,3-triazol-4-yl)isoxazolidines: A new class of C-nucleosides”, Molecules, 20(4): 5260-5275, (2015).
Büyükgüngör, O., Yavuz, S., Odabaşoğlu, M., Özkan, H., Pamir, Ö. and Yıldırır, Y., “Dimethyl trans-3-(4-bromo¬phen¬yl)-2-methyl¬isoxazolidine-4,5-dicarboxyl¬ate”, Acta Cryst., E65(Pt 9): o2207, (2009).
Andrade, M., Barros, M.T. and Pinto, R.C., “Exploiting microwave-assisted neat procedures: synthesis of N-aryl and N-alkylnitrones and their cycloaddition en route for isoxazolidines”, Tetrahedron, 64(46): 10521-10530, (2008).
Colacino, E., Nun, P., Colacino, F.M., Martinez, J. and Lamaty, F., “Solvent-free synthesis of nitrones in a ball-mill”, Tetrahedron, 64(23): 5569-5576, (2008).
Wagner, G. and Garland, T., “Synthesis of 5-trichloromethyl-Δ4-1,2,4-oxadiazolines and their rearrangement into formamidine derivatives”, Tetrahedron Lett., 49(22): 3596-3599, (2008).
Yijima, C., Tsujimoto, T., Suda, K. and Yamauchi, M., “13C and 1H NMR of α-arylnitrones. Substituent effects on the α-position of α-(p-substituted phenyl)nitrones”, Bull. Chem. Soc. Jpn., 59(7): 2165-2170, (1986).
Clinical and Laboratory Standards Institute. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically approved standard, 7th ed. M7-A7, (2006).
Clinical and Laboratory Standards Institute. Reference method for broth dilution antifungal susceptibility testing of yeasts approved standard, 3rd ed. M27-A3, vol 0, no 0, Replaces M27-A2, vol 22, no 15, (2007).
Iannazzo, D., Brunaccini, E., Giofre, S., Piperno, A., Romeo, G., Ronsisvalle, S., Chiacchio, M.A., Lanza, G. and Chiacchio, U., “Competitive formation of β-enaminones and 3-amino-2(5H)-furanones from the isoxazolidine system: a combined synthetic and quantum chemical study”, Eur. J. Org. Chem., 2010(30):5897-5905, (2010).
Alavi Nikje, M.M., Bigdeli, M.A. and Imanieh, H. A., “Facile and new method for the synthesis of α-aryl-N-methylnitrones in solvent-free media using silica gel-NaOH”, Phosphorus Sulfur Silicon Relat. Elem.,179(8):1465-1468, (2004).
Yavuz, S., Ozkan, H., Colak, N. and Yildirir, Y., “Fast method for synthesis of alkyl and aryl-N-methylnitrones”, Molecules,16(8):6677-83, (2011).
Marvaniya, H.M., Modi, K.N.and Sen, D.J., “Greener reactions under solvent free conditions”, Int. J. Drug and Res., 3(2):34-43, (2011).
Zangade, S.B., Mokle, S.S., Shinde, A.T. and Vibhute, Y.B., “An atom efficient, green synthesis of 2-pyrazoline derivatives under solvent-free conditions using grinding technique”, Green Chem. Lett. Rev., 6(2): 123-127, (2013).