Skip to main content
Log in

Synthesis, Fungistatic, Protistocidal, and Antibacterial Activity of 1-(3-Amino-2-Hydroxypropyl)Indoles

  • Published:
Russian Journal of Bioorganic Chemistry Aims and scope Submit manuscript

Abstract

A series of new indole derivatives containing the 3-amino-2-hydroxypropyl group at the nitrogen atom has been synthesized by the ring-opening of the oxirane cycle of 1-oxiranylmethylindoles. Their antibacterial, fungicidal, and protistocidal activities have been studied. Most of the synthesized compounds have been shown to exhibit a high protistocidal activity that several times exceeds that of the reference drug, baikoks (toltrazuril).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Kim, C.Y., Mahaney, P.E., McConnell, O., Zhang, Y., Manas, E., Ho, D.M., Deecher, D.C., and Trybulski, E.J., Bioorg. Med. Chem. Lett., 2009, vol. 19, pp. 5029–5032.

    Article  CAS  PubMed  Google Scholar 

  2. Liu, M., Huang, J., Chen, D.-X., and Jiang, C., Bioorg. Med. Chem. Lett., 2015, vol. 25, pp. 431–434.

    Article  CAS  PubMed  Google Scholar 

  3. Di Santo, R., Costi, M., Artico, M., Massa, S., Ragno, R., Marshall, G.R., and La Colla, P., Bioorg. Med. Chem., 2002, vol. 10, pp. 2511–2526.

    Article  PubMed  Google Scholar 

  4. Biradar, J.S., Rajesab, P., and Somappa, S.B., J. Chem., 2014, Article ID 579612. http://dx.doi.org/. 10.1155/2014/579612.

    Google Scholar 

  5. Gali, R., Banothu, J., Gondru, R., Bavantula, R., Velivela, Y., and Crooks, P.A., Bioorg. Med. Chem. Lett., 2015, vol. 25, pp. 106–112.

    Article  CAS  PubMed  Google Scholar 

  6. Gupta, R., Jain, A., Madan, Y., and Menghani, E., J. Het. Chem., 2014, vol. 51, pp. 1395–1403.

    Article  CAS  Google Scholar 

  7. Saundane, A.R., Verma, V.A., and Katkar, V.T., J. Chem., 2013, Article ID 148412. http://dx.doi.org/ 10.1155/2013/148412.

    Google Scholar 

  8. Singh, G.S., Al-kahraman, Y.M.S.A., Mpadi, D., and Yasinzaic, M., J. Het. Chem., 2015, vol. 52, pp. 614–619.

    Article  CAS  Google Scholar 

  9. Suzdalev, K.F., Den’kina,, S.V., Galenko-Yaroshevskii, P.A., Varlashkina, I.A., Cherednik, I.L., Sheikh-Zade, Yu.R., Taran, O.A., Takhchidi, Kh.P., Sakhnov, S.N., Dol’skaya, O.A., Lisitsyna, N.P., Bguasheva, B.A., and Bogus, S.K., 3-[1-(2-Hydroxy-3-piperidin-1-yl-propyl)-1H-indol-3-yl]-1-phenylpropenone hydrohalides having a local anesthetic and antiarrhythmic activity, RF Patent no. 2408592, Chem. Abstr., 2011, vol. 154, p. 125248.

    Google Scholar 

  10. Kucheryavenko, A.F., Spasov, A.A., Tian, M., and Suzdalev, K.F., Bull. Exp. Biol. Med., 2017, vol. 162, no. 6, pp. 758–761.

    Article  CAS  PubMed  Google Scholar 

  11. Suzdalev, K.F. and Babakova, M.N., Russ. J. Org. Chem., 2005, vol. 41, pp. 243–246.

    Article  Google Scholar 

  12. Zhungietu, G.I., Budylin, V.A., and Kost, A.N., Preparativnaya khimiya indola (Preparative Chemistry of Indol), Chişinau: ShTIINTsA, 1975, p. 197.

    Google Scholar 

  13. Tsukerman, S.I., Nikitchenko, V.M., Bugai, A.I., and Lavrushin, V.F., Khim. Geterotsikl. Soed., 1969, no. 2, pp. 268–272.

    Google Scholar 

  14. Popov, L.D. and Suzdalev, K.F. Russ. J. Org. Chem., 2016, vol. 52, no. 6, pp. 858–861.

    Article  Google Scholar 

  15. Fetisov, L.N., Zubenko, A.A., Bodryakov, A.N., and Bodryakova, M.A., Materialy mezhdunarodnogo parazitologicheskogo simpoziuma “Sovremennye problemy obshchei i chastnoi parazitologii” (Proc. Int. Parasitology Symposium "Modern Problems of General and Special Parasitilogy"), Saint Petersburg, 2012, pp. 70–73.

    Google Scholar 

  16. Rukovodstvo po eksperimental'nomu (doklinicheskomu) izucheniyu novykh farmakologicheskikh veshchestv (Guide on Experimental (Preclinical) Investigation of New Pharmacological Substancies), Khabriev, R.U., Ed., Moscow: Meditsyna, 2005, pp. 582–585.

  17. Semina, N.A., Sidorenko, S.V., Rezvan, S.P., Grudinina, S.A., Strachunskiim L.S., Stetsyuk, O.U., Kozlov, R.S., Eidel’shtein, M.V., Ved’mina, E.A., Stolyrova, L.G., Vasova, I.V., and Sereda, Z.S., Opredelenie chuvstvitel'nosti mikroorganizmov k antibakterial’nym preparatam. Metodicheskie ukazaniya. MUK 4.2.1890–04 (Determination of Microorganism Susceptibility to Antibiotics. Methodology Guidelines. MUK 4.2.1890–04), Moscow: Meditsyna, 2004.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to K. F. Suzdalev.

Additional information

Original Russian Text © K.F. Suzdalev, L.D. Popov, A.A. Zubenko, Yu.D. Drobin, L.N. Fetisov, A.N. Bodryakov, N.M. Serbinovskaya, 2018, published in Bioorganicheskaya Khimiya, 2018, Vol. 44, No. 2, pp. 217–224.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Suzdalev, K.F., Popov, L.D., Zubenko, A.A. et al. Synthesis, Fungistatic, Protistocidal, and Antibacterial Activity of 1-(3-Amino-2-Hydroxypropyl)Indoles. Russ J Bioorg Chem 44, 229–237 (2018). https://doi.org/10.1134/S106816201801017X

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S106816201801017X

Keywords

Navigation