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Effect of Structure of 1-Substituted Isatins on Direction of Their Reactions with Some Acetohydrazide Ammonium Derivatives

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Abstract

The reaction of 1-acylisatins with Girard’s reagent T proceeds with elimination of the acyl substituent and the formation of isatin-3-hydrazone with a quaternary nitrogen atom in the side chain. Depending on the structure of the substituent in position 1, 1-(aminomethyl)isatins reacted with the Girard’s reagent T to form hydrazones either with the elimination of the aminomethyl substituent or with its retention. Isatin derivatives containing no substituents in the aromatic fragment exhibit moderate activity against gram-positive bacteria S. aureus 209p and B. cereus 8035. Low hemotoxicity of the obtained compounds was revealed.

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REFERENCES

  1. Bogdanov, A.V., Musin, L.I., and Mironov, V.F., Arkivoc, 2015, vol. 6, p. 362. https://doi.org/10.3998/ark.5550190.p009.090

    Article  CAS  Google Scholar 

  2. Randell, N.M. and Kelly, T.L., Chem. Rec., 2018, vol. 18, p. 1. https://doi.org/10.1002/tcr.201800135

    Article  CAS  Google Scholar 

  3. Lin, Y.-Ch., Chen, F.-H., Chiang, Y.-Ch., Chueh, Ch.-Ch., and Chen, W.-Ch., ACS Appl. Mater. Interfaces, 2019, vol. 11, p. 34158. https://doi.org/10.1021/acsami.9b10943

    Article  CAS  PubMed  Google Scholar 

  4. Lee, Ju., Shin, E.-S., Kim, Y.-J., Noh, Yo.-Yo., and Yang, Ch., J. Mater. Chem. (C), 2020, vol. 8, p. 296. https://doi.org/10.1039/c9tc05641f

    Article  CAS  Google Scholar 

  5. Zhang, G., Chen, R., Sun, Y., Kang, B., Sun, M., Lu, H., Qiu, L., Cho, K., and Ding, Yu., J. Mater. Chem. (C), 2020, vol. 8, p. 1398. https://doi.org/10.1039/c9tc05374c

    Article  CAS  Google Scholar 

  6. Rout, Y., Chauhan, V., and Misra, R., J. Org. Chem., 2020, vol. 85, p. 4611. https://doi.org/10.1021/acs.joc.9b03267

    Article  CAS  PubMed  Google Scholar 

  7. Leite, A.C.L., Espíndola, J.W.P., de Oliveira Cardoso, M.V., and de Oliveira Filho, G.B., Curr. Med. Chem., 2019, vol. 26, p. 4323. https://doi.org/10.2174/0929867324666171023163752

    Article  CAS  PubMed  Google Scholar 

  8. Ding, Z., Zhou, M., and Zeng, C., Arch. Pharm. Chem. Life Sci., 2020, vol. 353. e1900367. https://doi.org/10.1002/ardp.201900367

  9. Moradi, R., Ziarani, G.M., and Lashgari, N., Arkivoc, 2017, vol. 1, p. 148. https://doi.org/10.3998/ark.5550190.p009.980

    Article  CAS  Google Scholar 

  10. Xua, Zh., Zhang, Sh., Gao, Ch., Fan, J., Zhao, F., Lu, Z.-Sh., and Feng, L.-Sh., Chinese Chem. Lett., 2017, vol. 28, p. 159. https://doi.org/10.1016/j.cclet.2016.07.032

    Article  CAS  Google Scholar 

  11. Pavlovska, T.L., Redkin, R.G., Lipson, V.V., and Atamanuk, D.V., Mol. Divers., 2016, vol. 20, p. 299. https://doi.org/10.1007/s11030-015-9629-8

    Article  CAS  PubMed  Google Scholar 

  12. Singh, G.S. and Desta, Z.Y., Chem. Rev., 2012, vol. 112, p. 6104. https://doi.org/10.1021/cr300135y

    Article  CAS  PubMed  Google Scholar 

  13. Gupta, A.K., Tulsyan, S., Bharadwaj, M., and Mehrotra, R., Top. Curr. Chem., 2019, vol. 377, p. 15. https://doi.org/10.1007/s41061-019-0240-9

    Article  CAS  Google Scholar 

  14. Melis, C., Meleddu, R., Angeli, A., Distinto, S., Bianco, G., Capasso, C., Cottiglia, F., Angius, R., Supuran, C.T., and Maccioni, E., J. Enzym. Inhibition Med. Chem., 2017, vol. 32, p. 68. https://doi.org/10.1080/14756366.2016.1235042

    Article  CAS  Google Scholar 

  15. Xu, Zh., Zhao, Sh.-J., Lu, Z.-Sh., Gao, F., Wang, Y., Zhang, F., Bai, L., and Deng, J.-L., Eur. J. Med. Chem., 2019, vol. 162, p. 396. https://doi.org/10.1016/j.ejmech.2018.11.032

    Article  CAS  PubMed  Google Scholar 

  16. Aneja, B., Khan, N.Sh., Khan, P., Queen, A., Hussain, A., Rehman, T., Alajmi, M.F., El-Seedi, H.R., Ali, Sh., Hassan, I., and Abid, M., Eur. J. Med. Chem., 2019, vol. 163, p. 840. https://doi.org/10.1016/j.ejmech.2018.12.026

    Article  CAS  PubMed  Google Scholar 

  17. Guo, H., Eur. J. Med. Chem., 2019, vol. 164, p. 678. https://doi.org/10.1016/j.ejmech.2018.12.017

    Article  CAS  PubMed  Google Scholar 

  18. Al-Wabli, R.I., Almomen, A.A., Almutairi, M.S., Keeton, A.B., Piazza, G.A., and Attia, M.I., Drug Des. Developm. Ther., 2020, vol. 14, p. 483. https://doi.org/10.2147/dddt.s227862

    Article  CAS  Google Scholar 

  19. Zhou, L.-M., Qu, R.-Y., and Yang, G.-F., Expert Opin. Drug Discov., 2020, p. 1. https://doi.org/10.1080/17460441.2020.1733526

  20. Qin, H.-L., Liu, J., Fang, W.-Y., Ravindar, L., and Rakesh, K.P., Eur. J. Med. Chem., 2020, vol. 194. 112245. https://doi.org/10.1016/j.ejmech.2020.112245

  21. Maddela, S., Mathew, G.E., Parambi, D.G.T., Aljoufi, F., and Mathew, B., Lett. Drug Design Discov., 2019, vol. 16, p. 220. https://doi.org/10.2174/1570180815666180516102100

    Article  CAS  Google Scholar 

  22. Varma, R.S. and Nobles, W.L., J. Med. Chem., 1967, vol. 10, p. 972. https://doi.org/10.1021/jm00317a061

    Article  CAS  PubMed  Google Scholar 

  23. Bogdanov, A.V., Vazykhova, A.M., Khasiyatullina, N.R., Krivolapov, D.B., Dobrynin, A.B., Voloshina, A.D., and Mironov, V.F., Chem. Heterocycl. Compd., 2016, vol. 52, p. 25. https://doi.org/10.1007/s10593-016-1826-6

    Article  CAS  Google Scholar 

  24. Ozgun, D.O., Yamali, C., Gul, H.I., Taslimi, P., Gulcin, I., Yanik, T., and Supuran, C.T., J. Enzyme Inhib. Med. Chem., 2016, vol. 31, p. 1498. https://doi.org/10.3109/14756366.2016.1149479

    Article  CAS  PubMed  Google Scholar 

  25. Bogdanov, A.V., Kutuzova, T.A., Krivolapov, D.B., Dobrynin, A.B., and Mironov, V.F., Russ. J. Gen. Chem., 2016, vol. 86, p. 539. https://doi.org/10.1134/S1070363216030087

    Article  CAS  Google Scholar 

  26. Bogdanov, A.V., Kutuzova, T.A., and Mironov, V.F., Russ. J. Gen. Chem., 2016, vol. 86, p. 756. https://doi.org/10.1134/S1070363216030440

    Article  CAS  Google Scholar 

  27. Bogdanov, A.V., Gil’fanova, A.R., Zaripova, I.F., and Mironov, V.F., Russ. J. Gen. Chem., 2018, vol. 88, p. 124. https://doi.org/10.1134/S1070363218010206

    Article  CAS  Google Scholar 

  28. Bogdanov, A.V. and Zaripova, I.F., Chem. Heterocycl. Compd., 2018, vol. 54, p. 686. https://doi.org/10.1007/s10593-018-2331-x

    Article  CAS  Google Scholar 

  29. Bogdanov, A.V., Zaripova, I.F., Voloshina, A.D., Strobykina, A.S., Kulik, N.V., Bukharov, S.V., and Mironov, V.F., Russ. J. Gen. Chem., 2018, vol. 88, p. 57. https://doi.org/10.1134/S1070363218010097

    Article  CAS  Google Scholar 

  30. Bogdanov, A.V., Zaripova, I.F., Voloshina, A.D., Strobykina, A.S., Kulik, N.V., Bukharov, S.V., Voronina, Ju.K., Khamatgalimov, A.R., and Mironov, V.F., Monatsh. Chem., 2018, vol. 149, p. 111. https://doi.org/10.1007/s00706-017-2049-y

    Article  CAS  Google Scholar 

  31. Bogdanov, A.V., Zaripova, I.F., Voloshina, A.D., Sapunova, A.S., Kulik, N.V., Voronina, Ju.K., and Mironov, V.F., Chem. Biodiversity, 2018, vol. 15, p. 1800088. https://doi.org/10.1002/cbdv.201800088

    Article  CAS  Google Scholar 

  32. Syakaev, V.V., Morozova, Ju.E., Bogdanov, A.V., Shalaeva, Ya.V., Ermakova, A.M., Voloshina, A.D., Zobov, V.V., Nizameev, I.R., Kadirov, M.K., Mironov, V.F., and Konovalov, A.I., Colloids Surf. (A), 2018, vol. 553, p. 368. https://doi.org/10.1016/j.colsurfa.2018.05.078

    Article  CAS  Google Scholar 

  33. Bogdanov, A.V., Zaripova, I.F., Voloshina, A.D., Sapunova, A.S., Kulik, N.V., Tsivunina, I.V., Dobrynin, A.B., and Mironov, V.F., J. Fluor. Chem., 2019, vol. 227. 109345. https://doi.org/10.1016/j.jfluchem.2019.109345

  34. Bogdanov, A.V., Zaripova, I.F., Mustafina, L.K., Voloshina, A.D., Sapunova, A.S., Kulik, N.V., and Mironov, V.F., Russ. J. Gen. Chem., 2019, vol. 89, p. 1368. https://doi.org/10.1134/S107036321907003X

    Article  CAS  Google Scholar 

  35. Bogdanov, A.V., Zaripova, I.F., Voloshina, A.D., Sapunova, A.S., Kulik, N.V., Bukharov, S.V., Voronina, Ju.K., Vanduykov, A.E., and Mironov, V.F., ChemistrySelect, 2019, vol. 4, p. 6162. https://doi.org/10.1002/slct.201901708

    Article  CAS  Google Scholar 

  36. Kale, R.R., Prasad, V., Mohapatra, P.P., and Tiwari, V.K., Monatsh. Chem., 2010, vol. 141, p. 1159. https://doi.org/10.1007/s00706-010-0378-1

    Article  CAS  Google Scholar 

  37. Briguglio, I., Piras, S., Corona, P., Gavini, E., Nieddu, M., Boatto, G., and Carta, A., Eur. J. Med. Chem., 2015, vol. 97, p. 612. https://doi.org/10.1016/j.ejmech.2014.09.089

    Article  CAS  PubMed  Google Scholar 

  38. Bogdanov, A.V., Kadomtseva, M.E., Bukharov, S.V., Voloshina, A.D., and Mironov, V.F., Russ. J. Org. Chem., 2020, vol. 56, p. 555. https://doi.org/10.1134/S107042802003032X

    Article  CAS  Google Scholar 

  39. Bogdanov, A.V., Musin, L.I., Il’in, A.V., and Mironov, V.F., J. Heterocycl. Chem., 2014, vol. 51, p. 1027. https://doi.org/10.1002/jhet.2011

    Article  CAS  Google Scholar 

  40. Sriram, D., Yogeeswari, P., Basha, J.S., Radha, D.R., and Nagaraja, V., Bioorg. Med. Chem., 2005, vol. 13, p. 5774. https://doi.org/10.1016/j.bmc.2005.05.063

    Article  CAS  PubMed  Google Scholar 

  41. Taher, A.T., Khalil, N.A., and Ahmed, E.M., Arch. Pharm. Res., 2011, vol 34, p. 1615. https://doi.org/10.1007/s12272-011-1005-3

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ACKNOWLEDGMENTS

The authors are grateful to the Collective Spectro-Analytical Center for Physico-Chemical Studies of the Structure, Properties and Composition of Substances and Materials of the Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences” for technical support.

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Authors and Affiliations

  1. A.E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”, 420088, Kazan, Russia

    A. V. Bogdanov, A. D. Voloshina, A. S. Sapunova, N. V. Kulik & V. F. Mironov

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  1. A. V. Bogdanov
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  2. A. D. Voloshina
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  3. A. S. Sapunova
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Bogdanov, A.V., Voloshina, A.D., Sapunova, A.S. et al. Effect of Structure of 1-Substituted Isatins on Direction of Their Reactions with Some Acetohydrazide Ammonium Derivatives. Russ J Gen Chem 90, 1591–1600 (2020). https://doi.org/10.1134/S1070363220090029

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