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Powerful Potential of Polyfluoroalkyl-Containing 4-Arylhydrazinylidenepyrazol-3-ones for Pharmaceuticals. / Burgart, Yanina V.; Elkina, Natalia A.; Shchegolkov, Evgeny V. et al.
In: Molecules, Vol. 28, No. 1, 59, 2023.

Research output: Contribution to journal › Article › peer-review

Harvard

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, vol. 28, no. 1, 59. https://doi.org/10.3390/molecules28010059

APA

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/molecules28010059

Vancouver

Burgart YV, Elkina NA, Shchegolkov EV, Krasnykh OP, Makhaeva GF, Triandafilova GA et al. Powerful Potential of Polyfluoroalkyl-Containing 4-Arylhydrazinylidenepyrazol-3-ones for Pharmaceuticals. Molecules. 2023;28(1):59. doi: 10.3390/molecules28010059

Author

Burgart, Yanina V. ; Elkina, Natalia A. ; Shchegolkov, Evgeny V. et al. / Powerful Potential of Polyfluoroalkyl-Containing 4-Arylhydrazinylidenepyrazol-3-ones for Pharmaceuticals. In: Molecules. 2023 ; Vol. 28, No. 1.

BibTeX

@article{58ff46869e224778afcefa3da27bfd05,
title = "Powerful Potential of Polyfluoroalkyl-Containing 4-Arylhydrazinylidenepyrazol-3-ones for Pharmaceuticals",
abstract = "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. {\textcopyright} 2022 by the authors.",
author = "Burgart, {Yanina V.} and Elkina, {Natalia A.} and Shchegolkov, {Evgeny V.} and Krasnykh, {Olga P.} and Makhaeva, {Galina F.} and Triandafilova, {Galina A.} and Solodnikov, {Sergey Yu.} and Boltneva, {Natalia P.} and Rudakova, {Elena V.} and Kovaleva, {Nadezhda V.} and Serebryakova, {Olga G.} and Ulitko, {Mariya V.} and Borisevich, {Sophia S.} and Gerasimova, {Natalia A.} and Evstigneeva, {Natalia P.} and Kozlov, {Sergey A.} and Korolkova, {Yuliya V.} and Minin, {Artem S.} and Belousova, {Anna V.} and Mozhaitsev, {Evgenii S.} and Klabukov, {Artem M.} and Saloutin, {Victor I.}",
note = "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 Y.V.B.): esterase profile of compounds; antioxidant activity in ABTS and FRAP tests were performed in the frame of IPAC RAS State Targets Project FFSN-2021-0005.",
year = "2023",
doi = "10.3390/molecules28010059",
language = "English",
volume = "28",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "1",

}

RIS

TY - JOUR

T1 - Powerful Potential of Polyfluoroalkyl-Containing 4-Arylhydrazinylidenepyrazol-3-ones for Pharmaceuticals

AU - Burgart, Yanina V.

AU - Elkina, Natalia A.

AU - Shchegolkov, Evgeny V.

AU - Krasnykh, Olga P.

AU - Makhaeva, Galina F.

AU - Triandafilova, Galina A.

AU - Solodnikov, Sergey Yu.

AU - Boltneva, Natalia P.

AU - Rudakova, Elena V.

AU - Kovaleva, Nadezhda V.

AU - Serebryakova, Olga G.

AU - Ulitko, Mariya V.

AU - Borisevich, Sophia S.

AU - Gerasimova, Natalia A.

AU - Evstigneeva, Natalia P.

AU - Kozlov, Sergey A.

AU - Korolkova, Yuliya V.

AU - Minin, Artem S.

AU - Belousova, Anna V.

AU - Mozhaitsev, Evgenii S.

AU - Klabukov, Artem M.

AU - Saloutin, Victor I.

N1 - 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 Y.V.B.): esterase profile of compounds; antioxidant activity in ABTS and FRAP tests were performed in the frame of IPAC RAS State Targets Project FFSN-2021-0005.

PY - 2023

Y1 - 2023

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85145721993

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=000910041900001

U2 - 10.3390/molecules28010059

DO - 10.3390/molecules28010059

M3 - Article

VL - 28

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 1

M1 - 59

ER -

ID: 33315825