Synthesis of Isoxazoles via 1,3-Dipolar Cycloaddition Reactions: Pharmacological Screening for Their Antioxidant and Antimicrobial Activities

Devirammanahalli Mahadevaswamy Lokeshwari; Kariyappa Ajay Kumar

doi:10.14233/ajchem.2017.20781

Issue

Vol. 29 No. 12 (2017): Vol 29 Issue 12

Issue Published : October 30, 2017

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis of Isoxazoles via 1,3-Dipolar Cycloaddition Reactions: Pharmacological Screening for Their Antioxidant and Antimicrobial Activities

https://doi.org/10.14233/ajchem.2017.20781

Devirammanahalli Mahadevaswamy Lokeshwari

Department of Chemistry, Yuvaraja’s College, Mysuru-570 005, India

Kariyappa Ajay Kumar

Department of Chemistry, Yuvaraja’s College, Mysuru-570 005, India

Corresponding Author(s) : Kariyappa Ajay Kumar

ajaykumar@ycm.uni-mysore.ac.in

Asian Journal of Chemistry, Vol. 29 No. 12 (2017): Vol 29 Issue 12
Article Published : October 30, 2017

Abstract

In the present study, we report the synthesis of series of novel substituted isoxazoles via 1,3-dipolar cycloaddition reaction. Nitrile oxides generated by the catalytic dehydrogenation of aldoximes by chloramine-T, were trapped in situ by 4-(furan-2-yl)but-3-en-2-one to obtain an isomeric mixture of isoxazoles. The structure of the new isoxazoles were elucidated by spectral and elemental analyses. The synthesized isoxazoles have been screened in vitro for their DPPH radical scavenging abilities and antimicrobial activities. Amongst the synthesized series, compound 1-(3-(4-chlorophenyl)-4-(furan-2-yl)-4,5-dihydroisoxazol-5-yl)ethanone (4f) exhibited excellent radical scavenging and antimicrobial susceptibilities.

Keywords

Antimicrobial Antioxidant Cycloaddition Dipolar Radical scavenging

Lokeshwari, D. M., & Kumar, K. A. (2017). Synthesis of Isoxazoles via 1,3-Dipolar Cycloaddition Reactions: Pharmacological Screening for Their Antioxidant and Antimicrobial Activities. Asian Journal of Chemistry, 29(12), 2660–2664. https://doi.org/10.14233/ajchem.2017.20781

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References

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K.A. Kumar, D.M. Lokeshwari and G.V. Kumar, Int. J. Pharm. Sci. Drug Res., 4, 236 (2012).
B. Frølund, A.T. Jørgensen, L. Tagmose, T.B. Stensbøl, H.T. Vestergaard, C. Engblom, U. Kristiansen, C. Sanchez, P. Krogsgaard-Larsen and T. Liljefors, J. Med. Chem., 45, 2454 (2002); https://doi.org/10.1021/jm020027o.
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N. Renuka, H.K. Vivek, G. Pavithra and K.A. Kumar, Russ. J. Bioorgan. Chem., 43, 197 (2017); https://doi.org/10.1134/S106816201702011X.
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References

B.P. Bandgar, L.K. Adsul, H.V. Chavan, S.S. Jalde, S.N. Shringare, R. Shaikh, R.J. Meshram, R.N. Gacche and V. Masand, Bioorg. Med. Chem. Lett., 22, 5839 (2012); https://doi.org/10.1016/j.bmcl.2012.07.080.

K.R. Raghavendra, N. Renuka, V.H. Kameshwar, B. Srinivasan, K. Ajay Kumar and S. Shashikanth, Bioorg. Med. Chem. Lett., 26, 3621 (2016); https://doi.org/10.1016/j.bmcl.2016.06.005.

K.A. Kumar, M. Govindaraju, N. Renuka and G.V. Kumar, J. Chem. Pharm. Res., 7, 250 (2015).

K.A. Kumar, M. Govindaraju and G.V. Kumar, Indian J. Heterocycl. Chem., 20, 183 (2010).

K.A. Kumar, M. Govindaraju, P. Jayaroopa and G.V. Kumar, Int. J. Pharm. Chem. Biol. Sci., 3, 91 (2013).

P. Jayaroopa, G.V. Kumar, N. Renuka and K.A. Kumar, IOSR J. Appl. Chem., 1, 20 (2012); https://doi.org/10.9790/5736-0142023.

K.M.L. Rai, N. Linganna, A. Hassner and C. Anjanamurthy, Org. Prep. Proced. Int., 24, 91 (1992); https://doi.org/10.1080/00304949209356711.

W.-T. Li, D.-R. Hwang, C.-P. Chen, C.-W. Shen, C.-L. Huang, T.-W. Chen, C.-H. Lin, Y.-L. Chang, Y.-Y. Chang, Y.-K. Lo, H.-Y. Tseng, C.-C. Lin, J.-S. Song, H.-C. Chen, S.-J. Chen, S.-H. Wu and C.-T. Chen, J. Med. Chem., 46, 1706 (2003); https://doi.org/10.1021/jm020471r.

J.W. Patterson, P.S. Cheung and M.J. Ernest, J. Med. Chem., 35, 507 (1992); https://doi.org/10.1021/jm00081a011.

K.A. Kumar, K.M.L. Rai and K.B. Umesha, J. Chem. Res. (S), 2001, 436 (2001); https://doi.org/10.3184/030823401103168389.

M.P. Giovannoni, C. Vergelli, C. Ghelardini, N. Galeotti, A. Bartolini and V. Dal Piaz, J. Med. Chem., 46, 1055 (2003); https://doi.org/10.1021/jm021057u.

M. Rowley, H.B. Broughton, I. Collins, R. Baker, F. Emms, R. Marwood, S. Patel, S. Patel, C.I. Ragan, S.B. Freedman and P.D. Leeson, J. Med. Chem., 39, 1943 (1996); https://doi.org/10.1021/jm960072u.

K.A. Kumar, D.M. Lokeshwari and G.V. Kumar, Int. J. Pharm. Sci. Drug Res., 4, 236 (2012).

B. Frølund, A.T. Jørgensen, L. Tagmose, T.B. Stensbøl, H.T. Vestergaard, C. Engblom, U. Kristiansen, C. Sanchez, P. Krogsgaard-Larsen and T. Liljefors, J. Med. Chem., 45, 2454 (2002); https://doi.org/10.1021/jm020027o.

J.J. Talley, D.L. Brown, J.S. Carter, M.J. Graneto, C.M. Koboldt, J.L. Masferrer, W.E. Perkins, R.S. Rogers, A.F. Shaffer, Y.Y. Zhang, B.S. Zweifel and K. Seibert, J. Med. Chem., 43, 775 (2000); https://doi.org/10.1021/jm990577v.

K.A. Kumar, K.M.L. Rai, K.B. Umesha and K.R. Prasad, Indian J. Chem., 40B, 269 (2001).

K.A. Kumar, K.M.L. Rai and K.B. Umesha, Tetrahedron, 57, 6993 (2001); https://doi.org/10.1016/S0040-4020(01)00612-3.

N. Renuka, H.K. Vivek, G. Pavithra and K.A. Kumar, Russ. J. Bioorgan. Chem., 43, 197 (2017); https://doi.org/10.1134/S106816201702011X.

D.K. Achutha, P. Mallappa, L.K. Neratur and A.K. Kariyappa, Chem. Data Coll., 2, 17 (2016); https://doi.org/10.1016/j.cdc.2016.06.003.

Issue

Vol. 29 No. 12 (2017): Vol 29 Issue 12

Synthesis of Isoxazoles via 1,3-Dipolar Cycloaddition Reactions: Pharmacological Screening for Their Antioxidant and Antimicrobial Activities

Corresponding Author(s) : Kariyappa Ajay Kumar

Abstract

Keywords

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