Main Article Content

Abstract

A series of thiophene conjugated isoxazoles were efficiently synthesized using a recyclable heterogeneous catalyst Amberlyst-15 in good yields. The synthesized new compounds 5(a-j) were characterized by spectral and elemental analysis and screened in vitro for their antimicrobial potencies. Amongst the synthesized series; compounds 5c and 5j having chloro substitution on both thiophene and aromatic ring exhibited excellent inhibition against the tested species.

Keywords

Amberlyst-15 Antibacterial Antifungal Chalcone Cyclocondensation

Article Details

How to Cite
Vagish, C., Renuka, N., Ajay Kumar, K., & Jayadevappa, H. (2020). Synthesis of Thienyl-Isoxazolines and in vitro Screening for their Antimicrobial Activity. Asian Journal of Organic & Medicinal Chemistry, 5(3), 208–212. https://doi.org/10.14233/ajomc.2020.AJOMC-P277

References

  1. C. Praveen, A. Kalyanasundaram and P.T. Perumal, Gold(III)-Catalyzed Synthesis of Isoxazoles by Cycloisomerization of a,b-Acetylenic Oximes, Synlett, 777 (2010); https://doi.org/10.1055/s-0029-1219342
  2. K.A. Kumar, K.M. Lokanatha Rai, K.B. Umesha and K.R. Prasad, Synthesis of 3-Aryl-5N-aryl-4,6-dioxopyrrolo[3,4-d]-7,8-dihydroiso-xazoles via 1,3-Dipolar Cycloaddition Reaction, Indian J. Chem., 40B, 269 (2001).
  3. K.B. Umesha, K.A. Kumar and K.M. Lokanatha Rai, A Novel Synthesis of Isoxazoles via 1,3-Dipolar Cycloaddition of Nitrile Oxides to Acetyl Acetone, Synth. Commun., 32, 1841 (2002); https://doi.org/10.1081/SCC-120004066
  4. D.M. Lokeshwari and K.A. Kumar, Synthesis of Isoxazoles via 1,3-Dipolar Cycloaddition Reactions: Pharmacological Screening for their Antioxidant and Antimicrobial Activities, Asian J. Chem., 29, 2660 (2017); https://doi.org/10.14233/ajchem.2017.20781
  5. K.A. Kumar, M. Govindaraju and G.V. Kumar, Synthesis of Isoxazoles via 1,3-Dipolar Cycloaddition Reactions and their Antimicrobial Activity, Indian J. Heterocycl. Chem., 20, 183 (2010).
  6. W. Chen, B. Wang, N. Liu, D. Huang, X. Wang and Y. Hu, Tandem Synthesis of 3-Halo-5-Substituted Isoxazoles from 1-Copper(I) Alkynes and Dihaloformaldoximes, Org. Lett., 16, 6140 (2014); https://doi.org/10.1021/ol503008t
  7. F. Himo, T. Lovell, R. Hilgraf, V.V. Rostovtsev, L. Noodleman, K.B. Sharpless and V.V. Fokin, Copper(I)-Catalyzed Synthesis of Azoles. DFT Study Predicts Unprecedented Reactivity and Intermediates, J. Am. Chem. Soc., 127, 210 (2005); https://doi.org/10.1021/ja0471525
  8. L. Johnson, J. Powers, F. Ma, K. Jendza, B. Wang, E. Meredith and N. Mainolfi, A Reliable Synthesis of 3-Amino-5-Alkyl and 5-Amino-3-Alkyl Isoxazoles, Synthesis, 45, 171 (2013); https://doi.org/10.1055/s-0032-1317935
  9. T. Gandhi, K. Kadam, A. Gupte, A. Gangopadhyay and R. Sharma, Alkyl Nitrites: Novel Reagents for One-Pot Synthesis of 3,5-Disubstituted Isoxazoles from Aldoximes and Alkynes, Synthesis, 48, 3996 (2016); https://doi.org/10.1055/s-0035-1561464
  10. S. Tang, J. He, Y. Sun, L. He and X. She, Efficient and Regioselective One-Pot Synthesis of 3-Substituted and 3,5-Disubstituted Isoxazoles, Org. Lett., 11, 3982 (2009); https://doi.org/10.1021/ol901626n
  11. E. Kobayashi and H. Togo, Facile One-Pot Transformation of Primary Alcohols into 3-Aryl- and 3-Alkyl-isoxazoles and -pyrazoles, Synthesis, 51, 3723 (2019); https://doi.org/10.1055/s-0039-1690102
  12. R. Harigae, K. Moriyama and H. Togo, Preparation of 3,5-Disubstituted Pyrazoles and Isoxazoles from Terminal Alkynes, Aldehydes, Hydrazines and Hydroxylamine, J. Org. Chem., 79, 2049 (2014); https://doi.org/10.1021/jo4027116
  13. P.V. Khairnar, T.-H. Lung, Y.-J. Lin, C.-Y. Wu, S.R. Koppolu, A. Edukondalu, P. Karanam and W. Lin, An Intramolecular Wittig Approach toward Heteroarenes: Synthesis of Pyrazoles, Isoxazoles and Chromenone-oximes, Org. Lett., 21, 4219 (2019); https://doi.org/10.1021/acs.orglett.9b01395
  14. M.L. Herrmann, R. Schleyerbach and B.J. Kirschbaum, Leflunomide: An Immunomodulatory Drug for the Treatment of Rheumatoid Arthritis and Other Autoimmune Diseases, ImmunoPharmacology, 47, 273 (2000); https://doi.org/10.1016/S0162-3109(00)00191-0
  15. P.S.V. Satyanarayana, N.K. Jain, S. Singh and S.K. Kulkarni, Effect of Selective Inhibition of Cyclooxygenase-2 on Lipopolysaccharide-Induced Hyperalgesia, InflammoPharmacology, 12, 57 (2004); https://doi.org/10.1163/156856004773121374
  16. K.A. Kumar, K.M. Lokanatha Rai and K.B. Umesha, Synthesis and Evaluation of Antifungal and Antibacterial Activity of Ethyl-3,5-diarylisoxazole-4-carboxylates, J. Chem. Res. (S), 436 (2001); https://doi.org/10.3184/030823401103168389
  17. G.V. Kumar, B.B.A. Khatoon, B.N. Mylarappa and K.A. Kumar, Novel Approach to the Synthesis of New Isoxazole Analogues as Potent Antioxidant Agents, J. Chem. Pharm. Res., 7, 1293 (2015).
  18. M. Govindaraju, G.V. Kumar and K.A. Kumar, Synthesis and Anti-microbial activity of Novel Isoxazolines by 1, 3-Dipolar Cycloaddition Reactions, Int. J. ChemTech. Res., 6, 886 (2014).
  19. B.A. Mendelsohn, S. Lee, S. Kim, F. Teyssier, V.S. Aulakh and M.A. Ciufolini, Oxidation of Oximes to Nitrile Oxides with Hypervalent Iodine Reagents, Org. Lett., 11, 1539 (2009); https://doi.org/10.1021/ol900194v
  20. S.Y. Hae, J.L. Eun, E.L. Jie, P. Woo-Kyu, B. Du-Jong, S.C. Yong, Y. Hun, C. Hyunah and P. Ae Nim, Synthesis and Biological Evaluation of Isoxazoline and Isoxazole Derivatives as 5-HT2A and 5-HT2C Receptor Ligands, Bull. Korean Chem. Soc., 30, 1873 (2009); https://doi.org/10.5012/bkcs.2009.30.8.1873
  21. Rakesh, D. Bruhn, D.B. Madhura, M. Maddox, R.B. Lee, A. Trivedi, L. Yang, M.S. Scherman, J.C. Gilliland, V. Gruppo, M.R. McNeil, A.J. Lenaerts, B. Meibohm and R.E. Lee, Antitubercular Nitrofuran Isoxazolines with Improved Pharmacokinetic Properties, Bioorg. Med. Chem., 20, 6063 (2012); https://doi.org/10.1016/j.bmc.2012.08.023
  22. R.E. Sammelson, T. Ma, L.J. Galietta, A.S. Verkman and M.J. Kurth, 3-(2-Benzyloxyphenyl)isoxazoles and Isoxazolines: Synthesis and Evaluation as CFTR Activators, Bioorg. Med. Chem. Lett., 13, 2509 (2003); https://doi.org/10.1016/S0960-894X(03)00482-7
  23. M.G. Prabhudeva, S. Bharath, A.D. Kumar, S. Naveen, N.K. Lokanath, B.N. Mylarappa and K.A. Kumar, Design and Environmentally benign Synthesis of Novel Thiophene Appended Pyrazole Analogues as Anti-inflammatory and Radical Scavenging Agents: Crystallographic, in silico Modeling, Docking and SAR Characterization, Bioorg. Chem., 73, 109 (2017); https://doi.org/10.1016/j.bioorg.2017.06.004
  24. N. Renuka, H.K. Vivek, G. Pavithra and K.A. Kumar, Synthesis of Coumarin Appended Pyrazolyl-1,3,4-oxadiazoles and Pyrazolyl-1,3,4-thiadiazoles: Evaluation of their in vitro Antimicrobial and Antioxidant Activities and Molecular Docking Studies, Russ. J. Bioorganic Chem., 43, 197 (2017); https://doi.org/10.1134/S106816201702011X