دورية أكاديمية
Powerful Potential of Polyfluoroalkyl-Containing 4-Arylhydrazinylidenepyrazol-3-ones for Pharmaceuticals
| العنوان: | Powerful Potential of Polyfluoroalkyl-Containing 4-Arylhydrazinylidenepyrazol-3-ones for Pharmaceuticals |
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| المؤلفون: | Burgart, Y. V., Elkina, N. A., Shchegolkov, E. V., Krasnykh, O. P., Makhaeva, G. F., Triandafilova, G. A., Solodnikov, S. Y., Boltneva, N. P., Rudakova, E. V., Kovaleva, N. V., Serebryakova, O. G., Ulitko, M. V., Borisevich, S. S., Gerasimova, N. A., Evstigneeva, N. P., Kozlov, S. A., Korolkova, Y. V., Minin, A. S., Belousova, A. V., Mozhaitsev, E. S., Klabukov, A. M., Saloutin, V. I. |
| المصدر: | Molecules |
| بيانات النشر: | MDPI |
| سنة النشر: | 2023 |
| المجموعة: | Ural Federal University (URFU): ELAR / Уральский федеральный университет: электронный архив УрФУ |
| مصطلحات موضوعية: | 4-ARYLHYDRAZINYLIDENEPYRAZOL-3-ONES, ADME PROFILE, ANTIMICROBIAL ACTIVITY, ANTINOCICEPTIVE EFFECT, ANTIOXIDANT ACTIVITY, CARBOXYLESTERASE INHIBITOR, CYTOTOXICITY, TRPV1 RECEPTOR INHIBITOR, ANTIOXIDANT, DICLOFENAC, DRUG, CHEMISTRY, HUMAN, MOLECULAR DOCKING, ANTIOXIDANTS, HUMANS, MOLECULAR DOCKING SIMULATION, PHARMACEUTICAL PREPARATIONS |
| الوصف: | 4-Arylhydrazinylidene-5-(polyfluoroalkyl)pyrazol-3-ones (4-AHPs) were found to be obtained by the regiospecific cyclization of 2-arylhydrazinylidene-3-(polyfluoroalkyl)-3-oxoesters with hydrazines, by the azo coupling of 4-nonsubstituted pyrazol-5-oles with aryldiazonium chlorides or by the firstly discovered acid-promoted self-condensation of 2-arylhydrazinylidene-3-oxoesters. All the 4-AHPs had an acceptable ADME profile. Varying the substituents in 4-AHPs promoted the switching or combining of their biological activity. The polyfluoroalkyl residue in 4-AHPs led to the appearance of an anticarboxylesterase action in the micromolar range. An NH-fragment and/or methyl group instead of the polyfluoroalkyl one in the 4-AHPs promoted antioxidant properties in the ABTS, FRAP and ORAC tests, as well as anti-cancer activity against HeLa that was at the Doxorubicin level coupled with lower cytotoxicity against normal human fibroblasts. Some Ph-N-substituted 4-AHPs could inhibit the growth of N. gonorrhoeae bacteria at MIC 0.9 μg/mL. The possibility of using 4-AHPs for cell visualization was shown. Most of the 4-AHPs exhibited a pronounced analgesic effect in a hot plate test in vivo at and above the diclofenac and metamizole levels except for the ones with two chlorine atoms in the aryl group. The methylsulfonyl residue was proved to raise the anti-inflammatory effect also. A mechanism of the antinociceptive action of the 4-AHPs through blocking the TRPV1 receptor was proposed and confirmed using in vitro experiment and molecular docking. © 2022 by the authors. ; FFSN-2021-0005; Russian Foundation for Basic Research, РФФИ: 20-03-00312; Russian Science Foundation, RSF: 21-13-00390 ; This work was financially supported by the Russian Science Foundation (grant No 21-13-00390 for V.I.S.): the synthesis and analysis of compounds, antimicrobial evaluation, cytotoxicity, analgesic and anti-inflammatory activity, mechanism of analgesia, molecular docking; by the Russian Foundation for Basic Research (grant No 20-03-00312 for ... |
| نوع الوثيقة: | article in journal/newspaper |
| وصف الملف: | application/pdf |
| اللغة: | English |
| ردمك: | 978-85-14-57219-0 85-14-57219-9 |
| تدمد: | 1420-3049 |
| العلاقة: | Burgart, YV, Elkina, NA, Shchegolkov, EV, Krasnykh, OP, Makhaeva, GF, Triandafilova, GA, Solodnikov, SY, Boltneva, NP, Rudakova, EV, Kovaleva, NV, Serebryakova, OG, Ulitko, MV, Borisevich, SS, Gerasimova, NA, Evstigneeva, NP, Kozlov, SA, Korolkova, YV, Minin, AS, Belousova, AV, Mozhaitsev, ES, Klabukov, AM & Saloutin, VI 2023, 'Powerful Potential of Polyfluoroalkyl-Containing 4-Arylhydrazinylidenepyrazol-3-ones for Pharmaceuticals', Molecules, Том. 28, № 1, 59. https://doi.org/10.3390/molecules28010059Test; Burgart, Y. V., Elkina, N. A., Shchegolkov, E. V., Krasnykh, O. P., Makhaeva, G. F., Triandafilova, G. A., Solodnikov, S. Y., Boltneva, N. P., Rudakova, E. V., Kovaleva, N. V., Serebryakova, O. G., Ulitko, M. V., Borisevich, S. S., Gerasimova, N. A., Evstigneeva, N. P., Kozlov, S. A., Korolkova, Y. V., Minin, A. S., Belousova, A. V., . Saloutin, V. I. (2023). Powerful Potential of Polyfluoroalkyl-Containing 4-Arylhydrazinylidenepyrazol-3-ones for Pharmaceuticals. Molecules, 28(1), [59]. https://doi.org/10.3390/molecules28010059Test; Final; All Open Access, Gold, Green; https://www.scopus.com/inward/record.uri?eid=2-s2.0-85145721993&doi=10.3390%2fmolecules28010059&partnerID=40&md5=40abed089c93b2d2117287a0bae505d0Test; https://www.mdpi.com/1420-3049/28/1/59/pdf?version=1672046166Test; http://elar.urfu.ru/handle/10995/130503Test; 85145721993; 000910041900001 |
| DOI: | 10.3390/molecules28010059 |
| الإتاحة: | https://doi.org/10.3390/molecules28010059Test http://elar.urfu.ru/handle/10995/130503Test https://www.mdpi.com/1420-3049/28/1/59/pdf?version=1672046166Test |
| حقوق: | info:eu-repo/semantics/openAccess ; cc-by ; https://creativecommons.org/licenses/by/4.0Test/ |
| رقم الانضمام: | edsbas.3204EB77 |
| قاعدة البيانات: | BASE |
Full Text Finder | ردمك: | 9788514572190 8514572199 |
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| تدمد: | 14203049 |
| DOI: | 10.3390/molecules28010059 |