Synthesis and biological testing of 3,5-bis(arylidene)-4-piperidone conjugates with 2,5-dihydro-5H-1,2-oxaphospholenes
Copyright © 2022 Elsevier Ltd. All rights reserved..
Using the methodology of "click" chemistry, a series of conjugates of 3,5-bis(benzylidene)-1-(prop-2-yn)piperidin-4-ones with 4-alkyl-3-azidomethyl-2-ethoxy-2,5-dihydro-5H-1,2 oxaphosphol 2-oxides was synthesized. All newly obtained compounds 8-18 were characterized by 1H, 13C, 31P, 19F NMR and IR spectroscopy. The potential antitumor activity of the synthesized conjugates8-18was studied in terms of their ability to influence the viability of variouscancercell lines, including A549, SH-SY5Y, Hep-2, and HeLa. Compound 15, which contains two fluorine atoms in the benzene ring, was shown to be the most promising. The mechanism of the cytotoxic action of this conjugate is supposed to be associated with the ability to inhibit the glycolytic profile of transformed cells.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2022 |
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| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:74 |
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| Enthalten in: |
Bioorganic & medicinal chemistry letters - 74(2022) vom: 15. Okt., Seite 128940 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Neganova, Margarita E [VerfasserIn] |
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| Links: |
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| Themen: |
“Click” chemistry |
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| Anmerkungen: |
Date Completed 31.08.2022 Date Revised 01.09.2022 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1016/j.bmcl.2022.128940 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 100 | 1 | |a Neganova, Margarita E |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Synthesis and biological testing of 3,5-bis(arylidene)-4-piperidone conjugates with 2,5-dihydro-5H-1,2-oxaphospholenes |
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| 500 | |a Date Completed 31.08.2022 | ||
| 500 | |a Date Revised 01.09.2022 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Copyright © 2022 Elsevier Ltd. All rights reserved. | ||
| 520 | |a Using the methodology of "click" chemistry, a series of conjugates of 3,5-bis(benzylidene)-1-(prop-2-yn)piperidin-4-ones with 4-alkyl-3-azidomethyl-2-ethoxy-2,5-dihydro-5H-1,2 oxaphosphol 2-oxides was synthesized. All newly obtained compounds 8-18 were characterized by 1H, 13C, 31P, 19F NMR and IR spectroscopy. The potential antitumor activity of the synthesized conjugates8-18was studied in terms of their ability to influence the viability of variouscancercell lines, including A549, SH-SY5Y, Hep-2, and HeLa. Compound 15, which contains two fluorine atoms in the benzene ring, was shown to be the most promising. The mechanism of the cytotoxic action of this conjugate is supposed to be associated with the ability to inhibit the glycolytic profile of transformed cells | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 4 | |a 1,2,3-Triazole | |
| 650 | 4 | |a 1,2-Oxaphospholene | |
| 650 | 4 | |a Antitumor activity | |
| 650 | 4 | |a Glycolysis | |
| 650 | 4 | |a Heterocycles | |
| 650 | 4 | |a Phosphorus | |
| 650 | 4 | |a “Click” chemistry | |
| 650 | 7 | |a Antineoplastic Agents |2 NLM | |
| 650 | 7 | |a Piperidones |2 NLM | |
| 700 | 1 | |a Aleksandrova, Yulia R |e verfasserin |4 aut | |
| 700 | 1 | |a Nikolaeva, Natalia S |e verfasserin |4 aut | |
| 700 | 1 | |a Brel, Valery K |e verfasserin |4 aut | |
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