Some cyano-substituted spiro-linked pyrazolines and pyrrolidines with antimicrobial activity
This work summarizes one-pot synthetic approaches to spiro-fused (di)azoles, which are promising in terms of studying biological activity. Proposed approaches involve condensation reactions of (hetero)cyclic ketones, methylene active moieties, and N-nucleophiles, occurring under mild conditions by b...
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| Language: | English |
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Saratov State University
2024-12-01
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| Series: | Известия Саратовского университета. Новая серия: Серия Химия. Биология. Экология |
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| Online Access: | https://ichbe.sgu.ru/sites/ichbe.sgu.ru/files/text-pdf/2024/12/himiya_2024_4-374-379.pdf |
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| author | Meshcheryakova, Anna A. Borisova, Svetlana Vasilievna Konstantinova, Ekaterina A. Vidlatskaya, Daria V. Burygin, Gennady L. Sorokin, Vitaly Viktorovich |
| author_facet | Meshcheryakova, Anna A. Borisova, Svetlana Vasilievna Konstantinova, Ekaterina A. Vidlatskaya, Daria V. Burygin, Gennady L. Sorokin, Vitaly Viktorovich |
| author_sort | Meshcheryakova, Anna A. |
| collection | DOAJ |
| description | This work summarizes one-pot synthetic approaches to spiro-fused (di)azoles, which are promising in terms of studying biological activity. Proposed approaches involve condensation reactions of (hetero)cyclic ketones, methylene active moieties, and N-nucleophiles, occurring under mild conditions by both stepwise and concerted mechanisms. The antimicrobial activity of signals from the proposed approaches of cyanosubstituted spiro-membered pyrazolines and pyrrolidines against gram-negative (P. aeruginosa, E. coli) and gram-positive (S. aureus) losses has been studied (EC50 determination (μg/ml)).The well-known component of broad-spectrum antimicrobial drugs, ciprofl oxacin, has been used as a control. It has been found that 3-amino-2-(4-nitrophenyl)-1,2-diazaspiro[4.5]dec-3-ene-4-carbonitrile exhibits the greatest inhibitory eff ect against selected gram-negative bacteria. In this case, the phenyl substituent at the second nitrogen atom of the pyrazoline ring plays an important role, since its replacement with an aroyl fragment reduces the studied eff ect by several tens of times, regardless of the type of the second ring. Substituted spiroindolinopyrrolizidinedicarbonitriles, containing cyano groups at the 2nd carbon atom of the pyrrolizidine ring and a phenyl substituent at the fi rst, also exhibit a moderate and high inhibitory eff ect. For pairs with the same type of substituent position, compounds containing a 3,4 Cl2 substituent in the phenyl fragment have the greatest antimicrobial activity. |
| format | Article |
| id | doaj-art-0886e2f33dfe4e3b8e7d72f9fe063e13 |
| institution | DOAJ |
| issn | 1816-9775 2541-8971 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Saratov State University |
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| series | Известия Саратовского университета. Новая серия: Серия Химия. Биология. Экология |
| spelling | doaj-art-0886e2f33dfe4e3b8e7d72f9fe063e132025-08-20T02:57:22ZengSaratov State UniversityИзвестия Саратовского университета. Новая серия: Серия Химия. Биология. Экология1816-97752541-89712024-12-0124437437910.18500/1816-9775-2024-24-4-374-379Some cyano-substituted spiro-linked pyrazolines and pyrrolidines with antimicrobial activityMeshcheryakova, Anna A.0Borisova, Svetlana Vasilievna1Konstantinova, Ekaterina A.2Vidlatskaya, Daria V.3Burygin, Gennady L.4Sorokin, Vitaly Viktorovich5Saratov State University, 83, Astrakhanskaya str., Saratov, 410012, RussiaSaratov State University, 83, Astrakhanskaya str., Saratov, 410012, RussiaSaratov State University, 83, Astrakhanskaya str., Saratov, 410012, RussiaSaratov State University, 83, Astrakhanskaya str., Saratov, 410012, RussiaInstitute of Biochemistry and Physiology of Plants and Microorganisms of the Russian Academy of Sciences - Subdivision of the Federal State Budgetary Research Institution Saratov Federal Scientific Centre of the Russian Academy of Sciences (IBPPM RAS), 410049, Russia, Saratov, Entuziastov Avenue, 13Saratov State University, 83, Astrakhanskaya str., Saratov, 410012, RussiaThis work summarizes one-pot synthetic approaches to spiro-fused (di)azoles, which are promising in terms of studying biological activity. Proposed approaches involve condensation reactions of (hetero)cyclic ketones, methylene active moieties, and N-nucleophiles, occurring under mild conditions by both stepwise and concerted mechanisms. The antimicrobial activity of signals from the proposed approaches of cyanosubstituted spiro-membered pyrazolines and pyrrolidines against gram-negative (P. aeruginosa, E. coli) and gram-positive (S. aureus) losses has been studied (EC50 determination (μg/ml)).The well-known component of broad-spectrum antimicrobial drugs, ciprofl oxacin, has been used as a control. It has been found that 3-amino-2-(4-nitrophenyl)-1,2-diazaspiro[4.5]dec-3-ene-4-carbonitrile exhibits the greatest inhibitory eff ect against selected gram-negative bacteria. In this case, the phenyl substituent at the second nitrogen atom of the pyrazoline ring plays an important role, since its replacement with an aroyl fragment reduces the studied eff ect by several tens of times, regardless of the type of the second ring. Substituted spiroindolinopyrrolizidinedicarbonitriles, containing cyano groups at the 2nd carbon atom of the pyrrolizidine ring and a phenyl substituent at the fi rst, also exhibit a moderate and high inhibitory eff ect. For pairs with the same type of substituent position, compounds containing a 3,4 Cl2 substituent in the phenyl fragment have the greatest antimicrobial activity.https://ichbe.sgu.ru/sites/ichbe.sgu.ru/files/text-pdf/2024/12/himiya_2024_4-374-379.pdfspirooxoindolesisatin13-dipolar cycloadditionazomethine ylidesthree-component reaction3-amino-12-diazaspiro[4.5]non3-ene-4-carbonitriles2-diazaspiro[4.5]deca-3-ene-4-carbonitriles |
| spellingShingle | Meshcheryakova, Anna A. Borisova, Svetlana Vasilievna Konstantinova, Ekaterina A. Vidlatskaya, Daria V. Burygin, Gennady L. Sorokin, Vitaly Viktorovich Some cyano-substituted spiro-linked pyrazolines and pyrrolidines with antimicrobial activity Известия Саратовского университета. Новая серия: Серия Химия. Биология. Экология spirooxoindoles isatin 1 3-dipolar cycloaddition azomethine ylides three-component reaction 3-amino-1 2-diazaspiro[4.5]non3-ene-4-carbonitriles 2-diazaspiro[4.5]deca-3-ene-4-carbonitriles |
| title | Some cyano-substituted spiro-linked pyrazolines and pyrrolidines with antimicrobial activity |
| title_full | Some cyano-substituted spiro-linked pyrazolines and pyrrolidines with antimicrobial activity |
| title_fullStr | Some cyano-substituted spiro-linked pyrazolines and pyrrolidines with antimicrobial activity |
| title_full_unstemmed | Some cyano-substituted spiro-linked pyrazolines and pyrrolidines with antimicrobial activity |
| title_short | Some cyano-substituted spiro-linked pyrazolines and pyrrolidines with antimicrobial activity |
| title_sort | some cyano substituted spiro linked pyrazolines and pyrrolidines with antimicrobial activity |
| topic | spirooxoindoles isatin 1 3-dipolar cycloaddition azomethine ylides three-component reaction 3-amino-1 2-diazaspiro[4.5]non3-ene-4-carbonitriles 2-diazaspiro[4.5]deca-3-ene-4-carbonitriles |
| url | https://ichbe.sgu.ru/sites/ichbe.sgu.ru/files/text-pdf/2024/12/himiya_2024_4-374-379.pdf |
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