Abstract
Thiourea-based scaffolds are increasingly used in medicinal chemistry owing to their tunable structural properties. This study demonstrates the first examples of phenethylamine-based thiourea derivatives and their antimicrobial and antioxidant activities. All compounds exhibited strong antibacterial activity against tested bacteria known to cause nosocomial infections, which have acquired resistance to many antibiotics, and also strong antioxidant properties. Therefore, they can be evaluated as possible antibacterial and antioxidant agents in the treatment of bacterial infections and many health problems related to aging.
Similar content being viewed by others
REFERENCES
Azeem, S., Ataf, A.A., Ashfaq, M.Q., and Amin, B., J. Drug Des. Med. Chem., 2016, vol. 2, p. 10. https://doi.org/10.11648/j.jddmc.20160201.12
Lee, J., Kim, S.Y., Kang, M., Kil, M.J., Cho, H.K., Jin, M.K., Wang, Y., Toth, A., Pearce, L.V., Lundberg, D.J., Tran, R., and Blumberg, P.M., Bioorg. Med. Chem., 2004, vol. 12, p. 3411. https://doi.org/10.1016/j.bmc.2004.04.040
Du, X.H., Hansell, E., Engel, J.C., Caffrey, C.R., Cohen, F.E., and McKerrow, J.H., Chem. Biol., 2000, vol. 7, p. 733. https://doi.org/10.1016/s1074-5521(00)00018-1
Küçükgüzel, İ., Tatar, E., Küçükgüzel, Ş.G., Rollas, S., and De Clercq, E., Eur. J. Med. Chem., 2008, vol. 43, p. 381. https://doi.org/10.1016/j.ejmech.2007.04.010
D’Cruz, O.J., Dong, Y.H., and Uckun, F.M., Biochem. Biophys. Res. Commun., 2003, vol. 302, p. 253. https://doi.org/10.1016/s0006-291x(03)00161-x
Venkatesh, P. and Pandeya, S.N., Int. J. ChemTech Res., 2009, vol. 1, p. 733.
Saeed, A., Abbas, N., Rafique, H., Rashid, S., and Hameed, A., Chemistry, 2009, vol. 18, p. 152.
Saeed, S., Rashid, N., Jones, P.G., Ali, M., and Hussain, R., Eur. J. Med. Chem., 2010, vol. 45, p. 1323. https://doi.org/10.1016/j.ejmech.2009.12.016
Sambanthamoorthy, K., Sloup, R.E., Parashar, V., Smith, J.M., Kim, E.E., Semmelhack, M.F., Neiditch, M.B., and Waters, C.M., Antimicrob. Agents Chemother., 2012, vol. 56, p. 5202. https://doi.org/10.1128/aac.01396-12
Brito, T.O., Souza, A.X., Mota, Y.C.C., Morais, V.S.S., de Souza, L.T., de Fatima, A., Macedo, F., Jr., and Modolo, L.V., RSC Adv., 2015, vol. 5, p. 44507. https://doi.org/10.1039/C5RA07886E
Lim, H.D., Istyastono, E.P, van de Stolpe, A., Romeo, G., Gobbi, S., Schepers, M., Lahaye, R., Menge, W.M.B.P., Zuiderveld, O.B., Jongejan, A., Smits, R.A., Bakker, R.A., Haaksma, E.E.J., Leurs, R., and de Esch, I.J.P., Bioorg. Med. Chem., 2009, vol. 17, p. 3987. https://doi.org/10.1016/j.bmc.2009.04.007
You, J.C., Han, G.H., Lee, C.H., Song, D.N., and Chung, K.H., PCT Int Appl. WO2011159137A2, 2011.
Stellenboom, N. and Baykan, A.R., Russ. J. Org. Chem., 2019, vol. 55, p. 1951. https://doi.org/10.1134/s1070428019120248
Perez-Mayoral, E., Calvino-Casilda, V., Godino, M., Lopez-Peinado, A.J., and Martin-Aranda, R.M., Green Synthetic Approaches for Biologically Relevant Heterocycles, Brahmachari, G., Ed., Waltham, MA: Elsevier; 2015. p. 377.
El-Sayed, H.A., Moustafa, A.H., El-Torky, A.E., and Abd El-Salam, E.A., Russ. J. Gen. Chem., 2017, vol. 87, p. 2401. https://doi.org/10.1134/s107036321710022x
Phaniendra, A., Jestadi, D.B., and Periyasamy, L., Indian J. Clin. Biochem., 2015, vol. 30, p. 11. https://doi.org/10.1007/s12291-014-0446-0
Aksu, K., Ozgeris, B., Taslimi, P., Naderi, A., Gulcin, I., and Goksu, S., Arch. Pharm. (Weinheim), 2016, vol. 349, p. 944. https://doi.org/10.1002/ardp.201600183
Hanif, M., Saleem, M., Hussain, M.T., Rama, N.H., Zaib, S., Aslam, M.A.M., Jones, P.G., and Iqbal, J., J. Braz. Chem. Soc., 2012, vol. 23, p. 854. https://doi.org/10.1590/S0103-50532012000500010
Ventola, C.L., Pharm. Ther., 2015, vol. 40, p. 277.
Villani, F.J. and King, M.S., Org. Synth., 1957, vol. 37, p. 6. https://doi.org/10.15227/orgsyn.037.0006
Parkanyi, C., Yuan, H.L., Cho, N.S., Jaw, H.J., Woodhouse, T.E., and Aung, T.L., J. Heterocycl. Chem., 1989, vol. 26, p. 1331. https://doi.org/10.1002/jhet.5570260520
Brindley, J.C., Caldwell, J.M., Meakins, G.D., Plackett, S.J., and Price, S.J., J. Chem. Soc., Perkin Trans. 1, 1987, p. 1153. https://doi.org/10.1039/P19870001153
Xue, S.-j. and Guan, Q., Chin. J. Org. Chem., 2002, vol. 22, p. 646.
Limban, C., Chifiriuc, M.C., Caproiu, M., Dumitrascu, F., Ferbinteanu, M., Pintilie, L., Stefaniu, A., Vlad, I.M., Bleotu, C., Marutescu, L.G., and Nuta, D.C., Molecules, 2020, vol. 25, p. 1478. https://doi.org/10.3390/molecules25071478
Limban, C., Nuta, D.C., Missir, A.V., Roman, R., Caproiu, M.T., Dumitrascu, F., Pintilie, L., Stefaniu, A., Chifiriuc, M.C., Popa, M., Zarafu, I., Arsene, A.L., Pirvu, C.E.D., Udeanu, D.I., and Papacocea, I.R., Processes, 2020, vol. 8, p. 503. https://doi.org/10.3390/pr8050503
Neiditch, M., Parashar, V., Semmelhack, M., Waters, C., and Karthik, S., PCT Int Appl. WO2014011663A1, 2014.
Limban, C., Missir, A.V., Chirita, I., Neagu, A., Draghici, C., and Chifiriuc, M.C., Rev. Chim. 2011, vol. 62, p. 168.
Badiceanu, C.D., Nuta, D.C., Missir, A.V., Hrubaru, M., Delcaru, C., Ditu, L.M., Chifiriuc, M.C., and Limban, C., Farmacia, 2018, vol. 66, p. 149.
Zhong, Z., Xing, R., Liu, S., Wang, L., Cai, S., and Li, P., Carbohydr. Res., 2008, vol. 343, p. 566. https://doi.org/10.1016/j.carres.2007.11.024
Ngaini, Z., Arif, M.A.M., Hussain, H., Mei, E.S., Tang, D., and Kamaluddin, D.H.A., Phosphorus, Sulfur Silicon Relat. Elem., 2012, vol. 187, p. 1. https://doi.org/10.1080/10426507.2011.562398
Rauf, M.K., Talib, A., Badshah, A., Zaib, S., Shoaib, K., Shahid, M., Flörke, U., Imtiaz, U.D., and Iqbal, J., Eur. J. Med. Chem., 2013, vol. 70, p. 487. https://doi.org/10.1016/j.ejmech.2013.10.012
ACKNOWLEDGMENTS
I would like to thank Prof. Dr. Arzu Görmez for her mentorship.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The author declares no conflict of interest.
Supplementary information
Rights and permissions
About this article
Cite this article
Özgeriş, B. Synthesis of Substituted Phenethylamine-Based Thioureas and Their Antimicrobial and Antioxidant Properties. Russ J Org Chem 57, 422–429 (2021). https://doi.org/10.1134/S1070428021030143
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428021030143