Synthesis, Self-Assembly in Crystalline Phase and Anti-Tumor Activity of 2-(2-/4-Hydroxybenzylidene)thiazolo[3,2-<i>a</i>]pyrimidines
A series of new thiazolo[3,2-<i>a</i>]pyrimidines different by aryl substituents in 2 and 5 positions are synthesized and characterized in solution as well as in the crystalline phase using <sup>1</sup>H and <sup>13</sup>C NMR-, IR-spectroscopies, mass-spectrometr...
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| Format: | Article |
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MDPI AG
2022-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/22/7747 |
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| author | Artem S. Agarkov Anna A. Nefedova Elina R. Gabitova Alexander S. Ovsyannikov Syumbelya K. Amerhanova Anna P. Lyubina Alexandra D. Voloshina Pavel V. Dorovatovskii Igor A. Litvinov Svetlana E. Solovieva Igor S. Antipin |
| author_facet | Artem S. Agarkov Anna A. Nefedova Elina R. Gabitova Alexander S. Ovsyannikov Syumbelya K. Amerhanova Anna P. Lyubina Alexandra D. Voloshina Pavel V. Dorovatovskii Igor A. Litvinov Svetlana E. Solovieva Igor S. Antipin |
| author_sort | Artem S. Agarkov |
| collection | DOAJ |
| description | A series of new thiazolo[3,2-<i>a</i>]pyrimidines different by aryl substituents in 2 and 5 positions are synthesized and characterized in solution as well as in the crystalline phase using <sup>1</sup>H and <sup>13</sup>C NMR-, IR-spectroscopies, mass-spectrometry methods, and single crystal X-ray diffraction (SCXRD). The SCXRD study revealed the role of intermolecular H-bonding in the formation of supramolecular architectures (racemic monomers, centrosymmetric racematic dimers, or homochiral 1D chains) of obtained thiazolo[3,2-<i>a</i>]pyrimidines derivatives depending on solvents (aprotic DMSO or protic EtOH) used upon the crystallization process. Moreover, the in vitro study of cytotoxicity toward different tumor cells showed their high or moderate efficiency with moderate cytotoxicity against normal liver cells which allows to consider the obtained thiazolo[3,2-<i>a</i>]pyrimidine derivatives as promising candidates for application as antitumor agents. |
| first_indexed | 2024-03-09T18:07:55Z |
| format | Article |
| id | doaj.art-63504108c0d44b719a287a50f3f0ed44 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T18:07:55Z |
| publishDate | 2022-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-63504108c0d44b719a287a50f3f0ed442023-11-24T09:20:23ZengMDPI AGMolecules1420-30492022-11-012722774710.3390/molecules27227747Synthesis, Self-Assembly in Crystalline Phase and Anti-Tumor Activity of 2-(2-/4-Hydroxybenzylidene)thiazolo[3,2-<i>a</i>]pyrimidinesArtem S. Agarkov0Anna A. Nefedova1Elina R. Gabitova2Alexander S. Ovsyannikov3Syumbelya K. Amerhanova4Anna P. Lyubina5Alexandra D. Voloshina6Pavel V. Dorovatovskii7Igor A. Litvinov8Svetlana E. Solovieva9Igor S. Antipin10Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova 8, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova 8, 420088 Kazan, RussiaDepartment of Organic and Medical Chemistry, Kazan Federal University, Kremlevskaya 18, 420008 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova 8, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova 8, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova 8, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova 8, 420088 Kazan, RussiaNational Research Center “Kurchatov Institute”, Akademika Kurchatova 1, 123182 Moscow, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova 8, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova 8, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova 8, 420088 Kazan, RussiaA series of new thiazolo[3,2-<i>a</i>]pyrimidines different by aryl substituents in 2 and 5 positions are synthesized and characterized in solution as well as in the crystalline phase using <sup>1</sup>H and <sup>13</sup>C NMR-, IR-spectroscopies, mass-spectrometry methods, and single crystal X-ray diffraction (SCXRD). The SCXRD study revealed the role of intermolecular H-bonding in the formation of supramolecular architectures (racemic monomers, centrosymmetric racematic dimers, or homochiral 1D chains) of obtained thiazolo[3,2-<i>a</i>]pyrimidines derivatives depending on solvents (aprotic DMSO or protic EtOH) used upon the crystallization process. Moreover, the in vitro study of cytotoxicity toward different tumor cells showed their high or moderate efficiency with moderate cytotoxicity against normal liver cells which allows to consider the obtained thiazolo[3,2-<i>a</i>]pyrimidine derivatives as promising candidates for application as antitumor agents.https://www.mdpi.com/1420-3049/27/22/7747thiazolo[3,2-<i>a</i>]pyrimidinessolid-state structurenon-covalent interactionscytotoxicityantitumor agentsmultiplex analysis of DNA markers of genotoxicity |
| spellingShingle | Artem S. Agarkov Anna A. Nefedova Elina R. Gabitova Alexander S. Ovsyannikov Syumbelya K. Amerhanova Anna P. Lyubina Alexandra D. Voloshina Pavel V. Dorovatovskii Igor A. Litvinov Svetlana E. Solovieva Igor S. Antipin Synthesis, Self-Assembly in Crystalline Phase and Anti-Tumor Activity of 2-(2-/4-Hydroxybenzylidene)thiazolo[3,2-<i>a</i>]pyrimidines Molecules thiazolo[3,2-<i>a</i>]pyrimidines solid-state structure non-covalent interactions cytotoxicity antitumor agents multiplex analysis of DNA markers of genotoxicity |
| title | Synthesis, Self-Assembly in Crystalline Phase and Anti-Tumor Activity of 2-(2-/4-Hydroxybenzylidene)thiazolo[3,2-<i>a</i>]pyrimidines |
| title_full | Synthesis, Self-Assembly in Crystalline Phase and Anti-Tumor Activity of 2-(2-/4-Hydroxybenzylidene)thiazolo[3,2-<i>a</i>]pyrimidines |
| title_fullStr | Synthesis, Self-Assembly in Crystalline Phase and Anti-Tumor Activity of 2-(2-/4-Hydroxybenzylidene)thiazolo[3,2-<i>a</i>]pyrimidines |
| title_full_unstemmed | Synthesis, Self-Assembly in Crystalline Phase and Anti-Tumor Activity of 2-(2-/4-Hydroxybenzylidene)thiazolo[3,2-<i>a</i>]pyrimidines |
| title_short | Synthesis, Self-Assembly in Crystalline Phase and Anti-Tumor Activity of 2-(2-/4-Hydroxybenzylidene)thiazolo[3,2-<i>a</i>]pyrimidines |
| title_sort | synthesis self assembly in crystalline phase and anti tumor activity of 2 2 4 hydroxybenzylidene thiazolo 3 2 i a i pyrimidines |
| topic | thiazolo[3,2-<i>a</i>]pyrimidines solid-state structure non-covalent interactions cytotoxicity antitumor agents multiplex analysis of DNA markers of genotoxicity |
| url | https://www.mdpi.com/1420-3049/27/22/7747 |
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