The study of the antimicrobial activity of ethylene-N,N’- bis(spiroindole-3,3’-pyrrolo[3,4-c]pyrrole-2a’,5a’-dihydro-2,2’,6’(1H,1’H,5’H)-trione) derivatives
DOI:
https://doi.org/10.24959/nphj.18.2202Keywords:
bis-spiro-2-oxindole, double drugs, bacteria, antibacterial agentsAbstract
Aim. To find compounds with the antimicrobial activity in the series of N,N’-bis(spiroindole-3,3’-pyrrolo[3,4-c] pyrrol-2a’,5a’-dihydro-2,2’,6’(1H,1’H,5’H)-trione) derivatives.
Materials and methods. The antimicrobial activity was studied by the agar diffusion method.
Results and discussion. The antimicrobial screening data revealed the pronounced biological activity of ethylene-N,N’-bis(spiroindole-3,3’-pyrrolo[3,4-c]pyrrol-2a’,5a’-dihydro-2,2’,6’(1H,1’H,5’H)-trione) derivatives against gramnegative (Proteus vulgaris, Escherichia coli, Pseudomonas aeruginosa) and grampositive (Staphylococcus aureus, Bacillus subtilis) bacteria and as well as against Candida albicans fungi.
Conclusions. The antibacterial activity of ethylene-N,N’-bis(spiroindole-3,3’-pyrrolo[3,4-c]pyrrol-2a’,5a’-dihydro-2,2’,6’(1H,1’H,5’H)-trione) derivatives has been studied. The compounds with a significant level of the antimicrobial activity against gramnegative bacteria (Proteus vulgaris, Escherichia coli, Pseudomonas aeruginosa), grampositive bacteria (Staphylococcus aureus, Bacillus subtilis), as well as against fungi (Candida albicans) have been found.
According to the data of the microbiological screening the most active compounds appeared to be ethylene-N,N’-bis(spiroindole-3,3’-pyrrolo[3,4-c]pyrrol-2a’,5a’-dihydro-2,2’,6’(1H,1’H,5’H)-trione) 1 and ethylene-N,N’-bis(spiroindole-3,3’-pyrrolo[3,4-c]pyrrol-5′-methyl-2a’,5a’-dihydro-2,2’,6’(1H,1’H,5’H)-trione) 2.
References
10 vedushchikh prichin smerti v mire. (2014). Informatcionnyi biulleten VOZ № 310.
Ball–Jones, N. R., Badillo, J. J., Franz, A. K. (2012). Strategies for the enantioselective synthesis of spirooxindoles. Organic & Biomolecular
Chemistry, 10 (27), 5165. doi: 10.1039/c2ob25184a
Shvetc, A. A., Kurbatov, S. V. (2012). Khimiia geterotcyklicheskikh soedinenii, 5, 859–866.
Palyulin, V. A., Osolodkin, D. I., Zefirov, N. S. (2010). Virtual Screening Workflow for Glycogen Synthase Kinase 3β Inhibitors: Convergence
of Ligand–based and Structure based Approaches. 6th German Conference on Chemoinformatics. Abstract Book, 73.
Zefirova, О. N., Zefirov, N. S. (2000). Vestnik Moskovskogo Universiteta, 2, 103–108.
Takayama, H., Kitajima, M. (2016). Monoterpenoid Bisindole Alkaloids. Graduate School of Pharmaceutical Sciences, 259–307.
Kim, S. Y., Roh, H. J., Seo, D. Y., Ryu, J. Y., Lee, J., Kim, J. N. (2017). Base–catalyzed one–pot synthesis of dispiro–1,3–dioxolane
bisoxindoles from N–methylisatin and methyl propiolate. Tetrahedron Letters, 58 (10), 914–918. doi: 10.1016/j.tetlet.2017.01.055
Qu, J., Fang, L., Ren, X.–D., Liu, Y., Yu, S.–S., Li, L., Ma, S.–G. (2013). Bisindole Alkaloids with Neural Anti–inflammatory Activity
from Gelsemium elegans. Journal of Natural Products, 76 (12), 2203–2209. doi: 10.1021/np4005536
Zhang, W., Huang, X.–J., Zhang, S.–Y., Zhang, D.–M., Jiang, R.–W., Hu, J.–Y., Ye, W.–C. (2015). Geleganidines A–C, Unusual Monoterpenoid
Indole Alkaloids from Gelsemium elegans. Journal of Natural Products, 78 (8), 2036–2044. doi: 10.1021/acs.jnatprod.5b00351
Redkin, R. G., Syumka, E. I., Shemchuk, L. A., Chernykh, V. P. (2017). Synthesis and antimicrobial activity of Bis–Derivatives of
a′,6a′ Dihydro–2’H–Spiro[Indole–3,1’–Pyrrolo[3,4–c]Pyrrole]–2,4’,6’(1H,3’H,5’H)–Trione. Journal of Applied Pharmaceutical Science,
(06), 069–078. doi: 10.7324/JAPS.2017.70610
Syumka, Y. I., Shemchuk, L. A., Chernykh, V. P., Redkin, R. G. (2018). The study of the three–component interaction between isatin,
α–amino acids and N,N’–di(3–carboxypropenoyl)–1,2–ethylenediamine and determination of the structure of the compounds obtained.
Žurnal Organìčnoï Ta Farmacevtičnoï Hìmìï, 16 (1(61)), 34–41. doi: 10.24959/ophcj.18.932
Bezuglyi, P. O. (2008). Farmatsevtychna khimiia. Vinnytsia: Nova knyha, 560.
Metody polucheniia khimicheskikh reaktivov i preparatov. (1960). Moscow, 85.
Balouiri, M., Sadiki, M., Ibnsouda, S. K. (2016). Methods for in vitro evaluating antimicrobial activity: A review. Journal of Pharmaceutical
Analysis, 6 (2), 71–79. doi: 10.1016/j.jpha.2015.11.005
Patel, J. B., Cockerill, F. R., Bradford, P. A. et al. (2015). Clinical and Laboratory Standards Institute. Performance Standards for Antimicrobial
Susceptibility Testing; Twenty–Second Informational Supplement. Document M100–S25, 35 (3).
Volianskyi, Yu. L., Hrytsenko, I. S., Shyrobokov, V. P. et al. (2004). Vyvchennia spetsyfichnoi aktyvnosti protymikrobnykh likarskykh
zasobiv. Kyiv: DFTs MOZ Ukrainy, 38.
Derzhavna farmakopeia Ukrainy, 1 vyd. (2001). Kharkiv: Ukrainskyi naukovyi farmakopeinyi tsentr yakosti likarskykh zasobiv.
Bakteriolohichnyi kontrol pozhyvnykh seredovyshch. (2000). Informatsiinyi lyst MOZ Ukrainy № 05. 4. 1 / 1670. Kyiv, 4.
American Society for Microbiology. Manual of Antimicrobial Susceptibility Testing. American Society for Microbiology. (2005). Washington,
Downloads
Published
Issue
Section
License
Copyright (c) 2018 National University of Pharmacy

This work is licensed under a Creative Commons Attribution 4.0 International License.
Authors who publish with this journal agree to the following terms:- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).