Is It Possible to Obtain a Product of the Desired Configuration from a Single Knoevenagel Condensation? Isomerization vs. Stereodefined Synthesis
The biological activity of compounds directly depends on the three-dimensional arrangement of affinity fragments since a high degree of pharmacophore compliance with the binding site is required. 3-Benzylidene oxindoles are privileged structures due to their wide spectrum of biological activity, syn...
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| Format: | Article |
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MDPI AG
2023-07-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/24/14/11339 |
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| author | Daria Novikova Tatyana Grigoreva Vladislav Gurzhiy Vyacheslav Tribulovich |
| author_facet | Daria Novikova Tatyana Grigoreva Vladislav Gurzhiy Vyacheslav Tribulovich |
| author_sort | Daria Novikova |
| collection | DOAJ |
| description | The biological activity of compounds directly depends on the three-dimensional arrangement of affinity fragments since a high degree of pharmacophore compliance with the binding site is required. 3-Benzylidene oxindoles are privileged structures due to their wide spectrum of biological activity, synthetic availability, and ease of modification. In particular, both kinase inhibitors and kinase activators can be found among 3-benzylidene oxindoles. In this work, we studied model compounds obtained via oxindole condensation with aldehydes and alkylphenones. These condensation products can exist in the form of <i>E</i>- and <i>Z</i>-isomers and also undergo isomerization in solutions. The factors causing isomeric transformation of these compounds were established. Comparative kinetic studies to obtain quantitative characteristics of UV-driven isomerization were first performed. The results obtained indicate dramatic differences in two subclasses, which should be considered when developing biologically active molecules. |
| first_indexed | 2024-03-11T01:00:32Z |
| format | Article |
| id | doaj.art-4f20c1ec203347ccb3ae6bdb5cd01599 |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-11T01:00:32Z |
| publishDate | 2023-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-4f20c1ec203347ccb3ae6bdb5cd015992023-11-18T19:37:50ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672023-07-0124141133910.3390/ijms241411339Is It Possible to Obtain a Product of the Desired Configuration from a Single Knoevenagel Condensation? Isomerization vs. Stereodefined SynthesisDaria Novikova0Tatyana Grigoreva1Vladislav Gurzhiy2Vyacheslav Tribulovich3Laboratory of Molecular Pharmacology, St. Petersburg State Institute of Technology (Technical University), St. Petersburg 190013, RussiaLaboratory of Molecular Pharmacology, St. Petersburg State Institute of Technology (Technical University), St. Petersburg 190013, RussiaCrystallography Department, Institute of Earth Sciences, St. Petersburg State University, St. Petersburg 199034, RussiaLaboratory of Molecular Pharmacology, St. Petersburg State Institute of Technology (Technical University), St. Petersburg 190013, RussiaThe biological activity of compounds directly depends on the three-dimensional arrangement of affinity fragments since a high degree of pharmacophore compliance with the binding site is required. 3-Benzylidene oxindoles are privileged structures due to their wide spectrum of biological activity, synthetic availability, and ease of modification. In particular, both kinase inhibitors and kinase activators can be found among 3-benzylidene oxindoles. In this work, we studied model compounds obtained via oxindole condensation with aldehydes and alkylphenones. These condensation products can exist in the form of <i>E</i>- and <i>Z</i>-isomers and also undergo isomerization in solutions. The factors causing isomeric transformation of these compounds were established. Comparative kinetic studies to obtain quantitative characteristics of UV-driven isomerization were first performed. The results obtained indicate dramatic differences in two subclasses, which should be considered when developing biologically active molecules.https://www.mdpi.com/1422-0067/24/14/11339benzylidene oxindole<i>E</i>-<i>Z</i> isomerismphotoinduced isomerizationphotostationary stateisomerization kinetics |
| spellingShingle | Daria Novikova Tatyana Grigoreva Vladislav Gurzhiy Vyacheslav Tribulovich Is It Possible to Obtain a Product of the Desired Configuration from a Single Knoevenagel Condensation? Isomerization vs. Stereodefined Synthesis International Journal of Molecular Sciences benzylidene oxindole <i>E</i>-<i>Z</i> isomerism photoinduced isomerization photostationary state isomerization kinetics |
| title | Is It Possible to Obtain a Product of the Desired Configuration from a Single Knoevenagel Condensation? Isomerization vs. Stereodefined Synthesis |
| title_full | Is It Possible to Obtain a Product of the Desired Configuration from a Single Knoevenagel Condensation? Isomerization vs. Stereodefined Synthesis |
| title_fullStr | Is It Possible to Obtain a Product of the Desired Configuration from a Single Knoevenagel Condensation? Isomerization vs. Stereodefined Synthesis |
| title_full_unstemmed | Is It Possible to Obtain a Product of the Desired Configuration from a Single Knoevenagel Condensation? Isomerization vs. Stereodefined Synthesis |
| title_short | Is It Possible to Obtain a Product of the Desired Configuration from a Single Knoevenagel Condensation? Isomerization vs. Stereodefined Synthesis |
| title_sort | is it possible to obtain a product of the desired configuration from a single knoevenagel condensation isomerization vs stereodefined synthesis |
| topic | benzylidene oxindole <i>E</i>-<i>Z</i> isomerism photoinduced isomerization photostationary state isomerization kinetics |
| url | https://www.mdpi.com/1422-0067/24/14/11339 |
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