Aminophthalide derivatives of cytisine, anabasine, and salsoline were obtained in high yields via condensation of the alkaloids with o-formylbenzoic acid. Their structures were proven using 1H and 13C NMR spectroscopy and data from 2D COSY 1H–1H and HMQC 1H–13C spectra. Studies of their antimicrobial activity showed moderate antimicrobial activity of 3-(N-cytisin-1-yl)isobenzofuran-1(3H)-one and 3-(N-salsolin-1-yl)isobenzofuran-1(3H)-one against Gram-positive test strain Staphylococcus aureus ATCC 6538 and Gram-negative test strain Escherichia coli ATCC 25922.
Similar content being viewed by others
References
S. A. Tyulyandin, Prakt. Onkol., 20, 4 (2019).
A. M. Gazaliev, O. A. Nurkenov, I. V. Kulakov, A. A. Ainabaev, and D. V. Bessonov, Russ. J. Appl. Chem., 79 (3), 508 (2006).
I. V. Kulakov, O. A. Nurkenov, D. M. Turdybekov, A. S. Mahmutova, S. B. Ahmetova, R. B. Sejdahmetova, and K. M. Turdybekov, Chem. Heterocycl. Compd., 46 (2), 240 (2010).
I. V. Kulakov, O. A. Nurkenov, S. B. Akhmetova, R. B. Seidakhmetova, and Z. M. Zhambekov, Pharm. Chem. J., 45 (1), 15 (2011).
I. V. Kulakov, Chem. Nat. Compd., 46, 68 (2010).
I. V. Kulakov, Chem. Nat. Compd., 47, 597 (2011).
O. A. Nurkenov, Zh. S. Nurmaganbetov, T. M. Seilkhanov, S. D. Fazylov, Zh. B. Satpayeva, K. M. Turdybekov, S. A. Talipov, and R. B. Seydakhmetova, Russ. J. Gen. Chem., 89, 2044 (2019).
I. V. Kulakov, Chem. Nat. Compd., 46, 66 (2010).
Z. Muldakhmetov, S. Fazylov, O. Nurkenov, A. Gazaliev, A. Sarsenbekova, I. Pustolaikina, Z. Nurmaganbetov, O. Seilkhanov, A. Alsfouk, E. Elkaeed, H. Eissa, and A. Metwaly, J. Plants, 11, 2283 (2022).
I. V. Palamarchuk, D. N. Ogurtsova, T. M. Seilkhanov, and I. V. Kulakov, Russ. J. Gen. Chem., 89, 2487 (2019).
I. P. Tsypysheva, A. V. Koval′skaya, A. N. Lobov, N. S. Makara, P. R. Petrova, E. I. Farafontova, L. F. Zainullina, Yu. V. Vakhitova, and F. S. Zarudii, Chem. Nat. Compd., 51, 910 (2015).
I. P. Tsypysheva, A. V. Koval′skaya, N. S. Makara, A. N. Lobov, I. A. Petrenko, E. G. Galkin, T. A. Sapozhnikova, F. S. Zarudii, and M. S. Yunusov, Chem. Nat. Compd., 48, 629 (2012).
I. P. Tsypysheva, H.-C. Lai, Y.-T. Kiu, A. V. Koval′skaya, D. O. Tsypyshev, S.-H. Huang, and C.-W. Lin, Bioorg. Med Chem. Lett., 54, 128437 (2020).
O. A. Nurkenov, A. M. Gazaliev, K. M. Turdybekov, A. B. Bukeeva, and I. V. Kulakov, Russ. J. Gen. Chem., 73 (6), 961 (2003).
I. V. Kulakov, O. A. Nurkenov, D. M. Turdybekov, A. A. Ainabaev, K. M. Turdybekov, and A. M. Gazaliev, Chem. Nat. Compd., 45, 66 (2009).
I. V. Kulakov, O. A. Nurkenov, D. M. Turdybekov, B. T. Ibragimov, S. A. Talipov, Z. M. Zhambekov, A. A. Ainabaev, and K. M. Turdybekov, Chem. Nat. Compd., 45, 209 (2009).
I. V. Kulakov and D. M. Turdybekov, Chem. Heterocycl. Compd., 46 (7), 839 (2010).
I. V. Kulakov, O. A. Nurkenov, D. M. Turdybekov, and K. M. Turdybekov, Chem. Nat. Compd., 46, 257 (2010).
I. V. Kulakov, O. A. Nurkenov, A. E. Arinova, D. M. Turdybekov, S. A. Talipov, and B. T. Ibragimov, Chem. Nat. Compd., 47, 777 (2011).
I. V. Kulakov and D. M. Turdybekov, Chem. Nat. Compd., 46, 586 (2010).
Zh. S. Nurmaganbetov, S. D. Fazylov, K. M. Turdybekov, O. A. Nurkenov, D. M. Turdybekov, G. K. Mukusheva, and Ye. V. Minaeva, Bull. Univ. Karaganda Chem., 2, 12 (2022).
D. A. Kharkevich, Principles of Pharmacology [in Russian], GEOTAR-Media, Moscow, 2015.
Acknowledgment
The work was financially supported by the Science Committee of the Ministry of Science and Higher Education of the Republic of Kazakhstan (PTsF No. BR05236438).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2023, pp. 967–970.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Nurkenov, O.A., Fazylov, S.D., Nurmaganbetov, Z.S. et al. Synthesis and Antimicrobial Activity of Phthalide Derivatives of Cytisine, Anabasine, and Salsoline. Chem Nat Compd 59, 1147–1150 (2023). https://doi.org/10.1007/s10600-023-04213-2
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-023-04213-2