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This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis of New Class of Functionalized Flavones/Isoxazole Derivatives-Nitrile oxide 1,3-Dipolar Cycloaddition
Corresponding Author(s) : Yerrabelly Hemasri
Asian Journal of Chemistry,
Vol. 33 No. 11 (2021): Vol 33 Issue 11, 2021
Abstract
A new series of functionalized flavone-isoxazole derivatives have been synthesized from alkyne tethered 3-hydroxy flavone by adopting facile synthetic method, intermolecular nitrile oxide 1,3-dipolar cycloaddition in the presence of eco-friendly sodium hypochloride oxidant under mild reaction conditions. Structures of all the synthesized compounds were established on the basis of 1H NMR, 13C NMR and ESI-mass.
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- A. Gupta, R. Jamatia, R.A. Patil, Y.-R. Ma and A.K. Pal, ACS Omega, 3, 7288 (2018); https://doi.org/10.1021/acsomega.8b00334
References
K. Yonekura-Sakakibara, Y. Higashi and R. Nakabayashi, Front. Plant Sci., 10, 943 (2019); https://doi.org/10.3389/fpls.2019.00943
M.L. Falcone-Ferreyra, S.P. Rius and P. Casati, Front. Plant Sci., 3, 222 (2012); https://doi.org/10.3389/fpls.2012.00222
S. Mondal and S.T. Rahaman, Pharm. Pharmacol. Int. J., 8, 91 (2020); https://doi.org/10.15406/ppij.2020.08.00285
V.M. Malikov and M.P. Yuldashev, Chem. Nat. Compd., 38, 358 (2002); https://doi.org/10.1023/A:1021638411150
T. Nagao, F. Abe, J. Kinjo and H. Okabe, Biol. Pharm. Bull., 25, 875 (2002); https://doi.org/10.1248/bpb.25.875
M. Sajid, C.N. Channakesavula, S.R. Stone and P. Kaur, Biomolecules, 11, 754 (2021); https://doi.org/10.3390/biom11050754
R.E. Mutha, A.U. Tatiya and S.J. Surana, Futur. J. Pharm. Sci., 7, 25 (2021); https://doi.org/10.1186/s43094-020-00161-8
J. Grassmann, S. Hippeli and E.F. Elstner, Plant Physiol. Biochem., 40, 471 (2002); https://doi.org/10.1016/S0981-9428(02)01395-5
S. Miura, J. Watanabe, M. Sano, T. Tomita, T. Osawa, Y. Hara and I. Tomita, Biol. Pharm. Bull., 18, 1 (1995); https://doi.org/10.1248/bpb.18.1
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J.M. Hamilton-Miller, Antimicrob. Agents Chemother., 39, 2375 (1995); https://doi.org/10.1128/AAC.39.11.2375
C. Han, Cancer Lett., 114, 153 (1997); https://doi.org/10.1016/S0304-3835(97)04647-8
D.F. Birt, S. Hendrich and W. Wang, Pharmacol. Ther., 90, 157 (2001); https://doi.org/10.1016/S0163-7258(01)00137-1
M. Cushman and D. Nagarathnam, J. Nat. Prod., 54, 1656 (1991); https://doi.org/10.1021/np50078a027
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R. Landolfi, R.L. Mower and M. Steiner, Biochem. Pharmacol., 33, 1525 (1984); https://doi.org/10.1016/0006-2952(84)90423-4
F. Perez-Vizcaino, M. Ibarra, A. L. Cogolludo, J. Duarte, F. ZaragozaArnaez, L. Moreno, G. Lopez-Lopez and J. Tamargo, J. Pharmacol. Exp. Ther., 301, 66 (2002); https://doi.org/10.1124/jpet.302.1.66
K. Polkowski and A.P. Mazurek, Acta Pol. Pharm. Drug Res, 57, 135 (2000).
O.H. Kan, I. Adachi, R. Kido and K. Hirose, J. Med. Chem., 10, 411 (1967); https://doi.org/10.1021/jm00315a028
T. Karabasanagouda, A.V. Adhikari and M. Girisha, Indian J. Chem., 48B, 430 (2009).
S. Dadiboyena and A. Nefzi, Eur. J. Med. Chem., 45, 4697 (2010); https://doi.org/10.1016/j.ejmech.2010.07.045
K.A. Kumar, M. Govindaraju, N. Renuka and G.V. Kumar, J. Chem. Pharm. Res., 7, 250 (2015).
A. Upadhyay, M. Gopal, C. Srivastava and N.D. Pandey, J. Pestic. Sci., 35, 464 (2010); https://doi.org/10.1584/jpestics.G10-40
R. Sun, Y. Li, L. Xiong, Y. Liu and Q. Wang, J. Agric. Food Chem., 59, 4851 (2011); https://doi.org/10.1021/jf200395g
T. Roth, A.M. Burger, W. Dengler, H. Willmann and H.H. Fiebig, Contrib. Oncol., 54, 145 (1999); https://doi.org/10.1159/000425830
K. Kobinata, S. Sekido, M. Uramoto, M. Ubukato, H. Osada, I. Yamaguchi and K. Isono, Agric. Biol. Chem., 55, 1415 (1991); https://doi.org/10.1080/00021369.1991.10870769
W.S. Hamama, M.E. Ibrahim and H.H. Zoorob, Synth. Commun., 43, 2393 (2013); https://doi.org/10.1080/00397911.2012.729281
R.M. Kumbhare, U.B. Kosurkar, M. Janaki Ramaiah, T.L. Dadmal, S.N.C.V.L. Pushpavalli and M. Pal-Bhadra, Bioorg. Med. Chem. Lett., 22, 5424 (2012); https://doi.org/10.1016/j.bmcl.2012.07.041
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P. Vitale and A. Scilimati, Adv. Heterocycl. Chem., 122, 1 (2017); https://doi.org/10.1016/bs.aihch.2016.10.001
L. Li, T.-D. Tan, Y.-Q. Zhang, X. Liu and L.-W. Ye, Org. Biomol. Chem., 15, 8483 (2017); https://doi.org/10.1039/C7OB01895A
T.M.V.D. Pinho e Melo, Eur. J. Org. Chem., 3363 (2010); https://doi.org/10.1002/ejoc.201000321
F. Heaney, Eur. J. Org. Chem., 3043 (2012); https://doi.org/10.1002/ejoc.201101823
A.V. Gulevich, A.S. Dudnik, N. Chernyak and V. Gevorgyan, Chem. Rev., 113, 3084 (2013); https://doi.org/10.1021/cr300333u
S. Roscales and J. Plumet, Org. Biomol. Chem., 16, 8446 (2018); https://doi.org/10.1039/C8OB02072H
T.M.V.D. Pinho e Melo, Curr. Org. Chem., 9, 925 (2005); https://doi.org/10.2174/1385272054368420
W. Jia-Jie, Y. Zhu and Z.-P. Zhan, Asian J. Org. Chem., 1, 108 (2012); https://doi.org/10.1002/ajoc.201200053
Y.J. Rao, T. Sowjanya, G. Thirupathi, N.Y.S. Murthy and S.S. Kotapalli, Mol. Divers., 22, 803 (2018); https://doi.org/10.1007/s11030-018-9833-4
A. Gupta, R. Jamatia, R.A. Patil, Y.-R. Ma and A.K. Pal, ACS Omega, 3, 7288 (2018); https://doi.org/10.1021/acsomega.8b00334