Abstract
A series of new substituted phosphonylated 1,3-oxazoles, 2-aryl-4-[1,2-bis(dialkoxyphosphoryl)vinyl]-5-ethoxy-1,3-oxazoles, was obtained by the reaction of ethynyldiphosphonic acid tetramethyl ester with diethyl 2-aroylaminomalonates. The reaction proceeds stereoselectively with the intermediate formation of the corresponding Z-2-aroylamino-2-[1,2-bis(dialkoxyphosphoryl)vinyl]malonates.
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REFERENCES
Joshi, S., Bisht, A.S., and Juyal, D., Pharm. Innov. J., 2017, vol. 6, no. 1, p. 109.
Swellmeen, L., Der Pharma Chemica, 2016, vol. 8, no. 13, p. 269.
Kakkar, S. and Narasimhan, D., BMC Chem., 2019, vol. 13, article number 16. https://doi.org/10.1186/s13065-019-0531-9
Zhang, H.Z., Zhao, Z.L., and Zhou, C.H., Eur. J. Med. Chem., 2018, vol. 144, p. 444. https://doi.org/10.1016/j.ejmech.2017.12.044
Ram, V.J., Sethi, A., Nath, M., and Pratap, R., in The Chemistry of Heterocycles, Elsevier, 2019, p. 149. https://doi.org/10.1016/B978-0-08-101033-4.00005-X
Zhang, W., Liu, W., Jiang, X., Jiang, F., Zhuang, H., and Fu, L., Eur. J. Med. Chem., 2011, vol. 46, no. 9, p. 3639. https://doi.org/10.1016/j.ejmech.2011.05.028
Aaglawe, M.J., Dhule, S.S., Bahekar, S.S., Wakte, P.S., and Shinde, D.B., J. Kor. Chem. Soc., 2003, vol. 47, no. 2, p. 133. https://doi.org/10.5012/jkcs.2003.47.2.133
Chiacchio, M.A., Lanza, G., Chiacchio, U., Giofrè, S.V., Romeo, R., Iannazzo, D., and Legnani, L., Curr. Med. Chem., 2019, vol. 26, no. 41, p. 7337. https://doi.org/10.2174/0929867326666181203130402
Zhang, X. and Jia, Y., Curr. Top. Med. Chem., 2020, vol. 20, no. 16, p. 1468. https://doi.org/10.2174/1568026620666200309161444
Yan, X., Wen, J., Zhou, L., Fan, L., Wang, X., and Xu, Z., Curr. Top. Med. Chem., 2020, vol. 20, no. 21, p. 1916. https://doi.org/10.2174/1568026620666200624161151
Moraski, G.C., Chang, M., Villegas-Estrada, A., Franzblau, S.G., Möllmann, M., and Miller, M.J., Eur. J. Med. Chem., 2010, vol. 45, no. 5, p. 1703. https://doi.org/10.1016/j.ejmech.2009.12.074
Lu, X., Liu, X., Wan, B., Franzblau, S.G., Chen, L., Zhou, C., and You, Q., Eur. J. Med. Chem., 2012, vol. 49, p. 164. https://doi.org/10.1016/j.ejmech.2012.01.007
Kuang, R., Shue, H.J., Blythin, D.J., Shih, N.Y., Gu, D., Chen, X., Schwerdt, J., Lin, L., Ting, P.C., Zhu, X., Aslanian, R., Piwinski, J.J., Xiao, L., Prelusky, D., Wu, P., Zhang, J., Zhang, X., Celly, C.S., Minnicozzi, M., Billah, M., and Wang, P., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 5150. https://doi.org/10.1016/j.bmcl.2007.06.092
Singh, N., Bhati, S.K., and Kumar, A., Eur. J. Med. Chem., 2008, vol. 43, no. 11, p. 2597. https://doi.org/10.1016/j.ejmech.2007.12.024
Parveen, M., Ali, A., Ahmed, S., Malla, A.M., Alam, M., Silva, P.S.P., Silva, M.R., and Lee, D.U., Spectrochim. Acta (A), 2013, vol. 104, p. 538. https://doi.org/10.1016/j.saa.2012.11.054
Seidler, J., McGovern, S.L., Doman, T.N., and Shoichet, B.K., J. Med. Chem., 2003, vol. 46, no. 21, p. 4477. https://doi.org/10.1021/jm030191r
Marcucci, F., Riva, R., Gomeni, R., Zavattini, G., Salva Lacombe, P., and Mussini, E., J. Pharm. Sci., 1978, vol. 67, no. 5, p. 705. https://doi.org/10.1002/jps.2600670537
Hearn, B.R., Shaw, S.J., and Myles, D.C., Compr. Med. Chem. II, 2007, vol. 7, p. 81. https://doi.org/10.1016/B0-08-045044-X/00205-4
Newman, D.J., Cragg, G.M., and Kingston, D.G.I., in The Practice of Medicinal Chemistry / Eds C.G. Wermuth, D. Aldous, P.R.D. Rognan. Academic Press, 2015, p. 101. https://doi.org/10.1016/B978-0-12-417205-0.00005-5
Osterman, I.A., Khabibullina, N.F., Komarova, E.S., Kasatsky, P., Kartsev, V.G., Bogdanov, A.A., Dontsova, O.A., Konevega, A.L., Sergiev, P.V., and Polikanov, Yu.S., Nucleic Acids Res., 2017, vol. 45, no. 12, p. 7507. https://doi.org/10.1093/nar/gkx413
Ghosh, A.K. and Liu, W., J. Org. Chem., 1997, vol. 62, no. 23, p. 7908. https://doi.org/10.1021/jo971616i
Ichiba, Т., Yoshida, W.Y., Scheuer, P.J., Higa, Т., and Gravalos, D.G., J. Am. Chem. Soc., 1991, vol. 113, no. 8, p. 3173. https://doi.org/10.1021/ja00008a056
Smith, T.E., Kuo, W.-H., Bock, V.D., Roizen, J.L., Balskus, E.P., and Theberge, A.B., Org. Lett., 2007, vol. 9, no. 6, p. 1153. https://doi.org/10.1021/ol070244p
Parsons, R.L.Jr. and Heathcock, C.H., J. Org. Chem., 1994, vol. 59, no. 17, p. 4733. https://doi.org/10.1021/jo00096a012
Fukuyama, T. and Xu, L., J. Am. Chem. Soc., 1993, vol. 115, no. 18, p. 8449. https://doi.org/10.1021/ja00071a065
Abdurakhmanova, E.R., Kondratyuk, K.M., Holovchenko, O.V., and Brovarets, V.S., J. Org. Pharm. Chem., 2018, vol. 16, no. 2, p. 13. https://doi.org/10.24959/ophcj.18.939
Iakovenko, I.N., Lukashuk, O.I., Kondratyuk, K.M., Golovchenko, A.V., Zhirnov, V.V., and Brovarets, V.S., J. Org. Pharm. Chem., 2013, vol. 11, no. 3, p. 43. https://doi.org/10.24959/ophcj.17.921
Nizhenkovska, I.V., Matskevych, K.V., Golovchenko, O.V., and Golovchenko, O.I., Maced. Pharm. Bull., 2020, vol. 66. Suppl. 1, p. 51. https://doi.org/10.33320/maced.pharm.bull.2020.66.03.025
Tsygankova, V.A., Andrusevich, Ya.V., Shtompel, O.I., Romaniuk, O.V., Yaikova, M.Yu., Hurenko, A.O., Solomyanny, R.M., Abdurakhmanova, E.R., Klyuchko, S.V., Holovchenko, O.V., Bondarenko, O.M., and Brovarets, V.S., Int. J. Med. Biotech. & Genetics, 2017, special issue S2:002, p. 10. https://doi.org/10.19070/2379-1020-SI02002
Abdurakhmanova, E.R., Brusnakov, M.Y., Golovchenko, O.V., Pilyo, S.G., Velychko, N.V., Harden, E.A., Prichard, M.N., James, S.H., Zhirnov, V.V., and Brovarets, V.S., Med. Chem. Res., 2020, vol. 29, p. 1669. https://doi.org/10.1007/s00044-020-02593-6
Semenyuta, I.V., Kobzar, O.L., Hodyna, D.M., Brovarets, V.S., and Metelytsia, L.O., Heliyon, 2019, vol. 5, no. 4, Article no. e01462. https://doi.org/10.1016/j.heliyon.2019.e01462
Egorov, D.M., Petrosyan, A.A., Piterskaya, Yu.L., Svintsitskaya, N.I., and Dogadina, A.V., Russ. J. Gen. Chem., 2018, vol. 88, no. 11, p. 2435. https://doi.org/10.1134/S1070363218110294
Kafarski, P., Lejczak, B., Kukhar, V.P., and Hudson, H.R., Aminophosphonic and Aminophosphinic Acids – Chemistry and Biological Activity, Chichester: John Wiley & Sons, 2000, p. 407.
Mucha, A., Kafarski, P., and Berlicki, L., J. Med. Chem., 2011, vol. 54, no. 17, p. 5955. https://doi.org/10.1021/jm200587f
Caillé, F., Buron, F., Tóth, É., and Suzenet, F., Eur. J. Org. Chem., 2011, vol. 11, p. 2120. https://doi.org/10.1002/ejoc.201001691
Shekhade, A., Didkovskii, N.G., Dogadina, A.V., and Ionin, B.I., Russ. J. Gen. Chem., 2004, vol. 74, no. 10, p. 1627. https://doi.org/10.1007/s11176-005-0071-y
ACKNOWLEDGMENTS
The authors are grateful to N.B. Viktorov (St. Petersburg State Institute of Technology) for providing diethyl 2-aroylaminomalonates.
Funding
This work was financially supported by the Russian Foundation for Basic Research (project no. 19-03-00365_A) using the equipment of the Engineering Center of the St. Petersburg State Institute of Technology (Technical University).
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N.I. Svintsitskaya is a member of the Editorial Board of the Russian Journal of General Chemistry. No conflict of interest was declared by the other authors.
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Translated from Zhurnal Obshchei Khimii, 2021, Vol. 91, No. 10, pp. 1594–1600 https://doi.org/10.31857/S0044460X21100164.
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Zhuravleva, P.A., Kolina, A.I., Svintsitskaya, N.I. et al. Synthesis of New 2-Aryl-4-[1,2-bis(dialkoxyphosphoryl)vinyl]-5-ethoxy-1,3-oxazoles. Russ J Gen Chem 91, 2031–2037 (2021). https://doi.org/10.1134/S1070363221100169
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DOI: https://doi.org/10.1134/S1070363221100169