Green synthesis, characterization & biological evaluation of 3,5-diphenyl isoxazole derivatives
Abstract
3,5-Diphenyl Isoxazole derivatives, constituting an important family of five-membered heterocycles with one oxygen atom and one nitrogen atom at adjacent positions is of immense importance because of its wide spectrum of biological activities and therapeutic potential. It is, therefore, of prime importance that the development of new synthetic strategies and designing of new isoxazole derivatives should be based on the most recent knowledge emerging from the latest research. This review is an endeavour to highlight the progress in the chemistry and biological activity of 3,5-Diphenyl isoxazole derivativesto the medicinal chemists for the development of clinically viable drugs using this information. One series of total 10 (3,5-Diphenyl Isoxazole) derivatives were synthesized but Compound A, Compound H & Compound I were designed elemental analysis and evaluated for antifungal and antioxidant activity.
Keywords:
Heterocyclic, 3, 5-Diphenyl Isoxazole derivatives, biological activity, Anti-fungal activity, Anti-oxidant activity
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References
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3. Khodabandlou S, Saraei M. Synthesis of novel isoxazole derivatives bearing kojic acid moiety and evaluation of their antimicrobial activity. Chemistry of Heterocyclic Compounds. 2021 Aug;57:823-7.
4. Ni T, Chi X, Xie F, Li L, Wu H, Hao Y, Wang X, Zhang D, Jiang Y. Design, synthesis, and evaluation of novel tetrazoles featuring isoxazole moiety as highly selective antifungal agents. European Journal of Medicinal Chemistry. 2023 Jan 15;246:115007.
5. Nie JP, Qu ZN, Chen Y, Chen JH, Jiang Y, Jin MN, Yu Y, Niu WY, Duan HQ, Qin N. Discovery and anti-diabetic effects of novel isoxazole based flavonoid derivatives. Fitoterapia. 2020 Apr 1;142:104499.
6. Praveen C, Kalyanasundaram A, Perumal PT. Gold (III)-catalyzed synthesis of isoxazoles by cycloisomerization of α, β-acetylenic oximes. Synlett. 2010 Mar;2010(05):777-81.
7. Duan M, Hou G, Zhao Y, Zhu C, Song C. Synthesis of Isoxazoles via One-Pot Oxidation/Cyclization Sequence from Propargylamines. The Journal of Organic Chemistry. 2022 Aug 1;87(16):11222-5.
8. Kadam KS, Gandhi T, Gupte A, Gangopadhyay AK, Sharma R. Alkyl nitrites: Novel reagents for one-pot synthesis of 3, 5-disubstituted isoxazoles from aldoximes and alkynes. Synthesis. 2016 Jun 22:3996-4008.
9. Tang S, He J, Sun Y, He L, She X. Efficient and regioselective one-pot synthesis of 3-substituted and 3, 5-disubstituted isoxazoles. Organic Letters. 2009 Sep 3;11(17):3982-5.
10. Tang S, He J, Sun Y, He L, She X. Efficient and regioselective one-pot synthesis of 3-substituted and 3, 5-disubstituted isoxazoles. Organic Letters. 2009 Sep 3;11(17):3982-5.
11. Tang S, He J, Sun Y, He L, She X. Efficient and regioselective one-pot synthesis of 3-substituted and 3, 5-disubstituted isoxazoles. Organic Letters. 2009 Sep 3;11(17):3982-5.
12. Tang S, He J, Sun Y, He L, She X. Efficient and regioselective one-pot synthesis of 3-substituted and 3, 5-disubstituted isoxazoles. Organic Letters. 2009 Sep 3;11(17):3982-5.
13. Harigae R, Moriyama K, Togo H. Preparation of 3, 5-disubstituted pyrazoles and isoxazoles from terminal alkynes, aldehydes, hydrazines, and hydroxylamine. The Journal of organic chemistry. 2014 Mar 7;79(5):2049-58.
14. Wenwen C, Bo W, Nan L, Dayun H, Xinyan W, Yuefei H. Tandem Synthesis of 3-Halo-5-Substituted Isoxazoles from 1-Copper (I) Alkynes and Dihaloformaldoximes.
15. Wang XD, Zhu LH, Liu P, Wang XY, Yuan HY, Zhao YL. Copper-catalyzed cascade cyclization reactions of diazo compounds with tert-butyl nitrite and alkynes: one-pot synthesis of isoxazoles. The Journal of Organic Chemistry. 2019 Nov 29;84(24):16214-21.
16. Xu J, Hamme Ii AT. Efficient access to isoxazoles from alkenes. Synlett. 2008 Apr;2008(06):919-23.
17. Hu M, He X, Niu Z, Yan Z, Zhou F, Shang Y. Synthesis of 3, 4, 5-trisubstituted isoxazoles by the 1, 3-dipolar cycloaddition reaction of α-azido acrylates and aromatic oximes. Synthesis. 2014 Jan 2:510-4.
18. Dellavalle PD, Cabrera A, Alem D, Larrañaga P, Ferreira F, Dalla Rizza M. Antifungal activity of medicinal plant extracts against phytopathogenic fungus Alternaria spp. Chilean journal of agricultural research. 2011 Apr 1;71(2):231.
19. Dawidowicz AL, Wianowska D, Olszowy M. On practical problems in estimation of antioxidant activity of compounds by DPPH method (Problems in estimation of antioxidant activity). Food chemistry. 2012 Apr 1;131(3):1037-43.
20. Hawash M, Jaradat N, Abualhasan M, Thaher M, Sawalhi R, Younes N, Shanaa A, Nuseirat M, Mousa A. In vitro and in vivo assessment of the antioxidant potential of isoxazole derivatives. Scientific Reports. 2022 Oct 29;12(1):18223.
Published
31/05/2024
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Hotta, S. K., Panigrahi, A., Maharana, A., Sabat, S. K., Behera, S. S., & Prusty, B. (2024). Green synthesis, characterization & biological evaluation of 3,5-diphenyl isoxazole derivatives. Journal of Innovations in Applied Pharmaceutical Science (JIAPS), 9(2), 1-6. https://doi.org/10.37022/jiaps.v9i2.586
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