Synthesis and biological testing of 3,5-bis(arylidene)-4-piperidone conjugates with 2,5-dihydro-5H-1,2-oxaphospholenes
Publication type: Journal Article
Publication date: 2022-10-01
scimago Q2
wos Q2
SJR: 0.472
CiteScore: 5.1
Impact factor: 2.2
ISSN: 0960894X, 14643405
PubMed ID:
35964843
Organic Chemistry
Drug Discovery
Biochemistry
Molecular Biology
Pharmaceutical Science
Clinical Biochemistry
Molecular Medicine
Abstract
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 conjugates 8–18 was studied in terms of their ability to influence the viability of various cancer cell 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.
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Total citations:
8
Citations from 2024:
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(62.5%)
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E. Neganova M. et al. Synthesis and biological testing of 3,5-bis(arylidene)-4-piperidone conjugates with 2,5-dihydro-5H-1,2-oxaphospholenes // Bioorganic and Medicinal Chemistry Letters. 2022. Vol. 74. p. 128940.
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E. Neganova M., Aleksandrova Y. R., Nikolaeva N. S., Brel V. K. Synthesis and biological testing of 3,5-bis(arylidene)-4-piperidone conjugates with 2,5-dihydro-5H-1,2-oxaphospholenes // Bioorganic and Medicinal Chemistry Letters. 2022. Vol. 74. p. 128940.
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TY - JOUR
DO - 10.1016/j.bmcl.2022.128940
UR - https://doi.org/10.1016/j.bmcl.2022.128940
TI - Synthesis and biological testing of 3,5-bis(arylidene)-4-piperidone conjugates with 2,5-dihydro-5H-1,2-oxaphospholenes
T2 - Bioorganic and Medicinal Chemistry Letters
AU - E. Neganova, Margarita
AU - Aleksandrova, Yulia R.
AU - Nikolaeva, N S
AU - Brel, Valery K.
PY - 2022
DA - 2022/10/01
PB - Elsevier
SP - 128940
VL - 74
PMID - 35964843
SN - 0960-894X
SN - 1464-3405
ER -
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@article{2022_E. Neganova,
author = {Margarita E. Neganova and Yulia R. Aleksandrova and N S Nikolaeva and Valery K. Brel},
title = {Synthesis and biological testing of 3,5-bis(arylidene)-4-piperidone conjugates with 2,5-dihydro-5H-1,2-oxaphospholenes},
journal = {Bioorganic and Medicinal Chemistry Letters},
year = {2022},
volume = {74},
publisher = {Elsevier},
month = {oct},
url = {https://doi.org/10.1016/j.bmcl.2022.128940},
pages = {128940},
doi = {10.1016/j.bmcl.2022.128940}
}
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