Modification of 3,5-bis(arylidene)-4-piperidone pharmacophore by phosphonate group using 1,2,3-triazole cycle as a linker for the synthesis of new cytostatics
Mikhail V. Makarov
1
,
Ekaterina Yu Rybalkina
2
,
Victor N. Khrustalev
1
,
Gerd-Volker Röschenthaler
3
Publication type: Journal Article
Publication date: 2014-09-20
scimago Q2
wos Q3
SJR: 0.470
CiteScore: 5.1
Impact factor: 3.1
ISSN: 10542523, 15548120
Organic Chemistry
General Pharmacology, Toxicology and Pharmaceutics
Abstract
Novel cytotoxic 3,5-bis(arylidene)-4-piperidones conjugated with phosphonate groups via 1,2,3-triazole ring have been synthesized and their antitumor properties have been evaluated. Synthetic route to these conjugates is based on 1,3-cycloaddition of diethyl (ω-azidoalkyl)phosphonates to 1-prop-2-ynyl-piperidin-4-one in the presence of Cu(I) catalyst followed by crotonic condensation of resulting 1,2,3-triazole with aromatic aldehydes. The synthesized phosphonate derivatives of 3,5-bis(arylidene)-4-piperidone series displayed high in vitro inhibitory properties toward HCT116 and MCF7 as well as CaoV3, A549, and PC3 human cancer cell lines with IC50 values in the range of 1.5–8.0 μM.
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12
Total citations:
12
Citations from 2024:
4
(33.33%)
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GOST
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Makarov M. V. et al. Modification of 3,5-bis(arylidene)-4-piperidone pharmacophore by phosphonate group using 1,2,3-triazole cycle as a linker for the synthesis of new cytostatics // Medicinal Chemistry Research. 2014. Vol. 24. No. 4. pp. 1753-1762.
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Makarov M. V., Rybalkina E. Yu., Khrustalev V. N., Röschenthaler G. Modification of 3,5-bis(arylidene)-4-piperidone pharmacophore by phosphonate group using 1,2,3-triazole cycle as a linker for the synthesis of new cytostatics // Medicinal Chemistry Research. 2014. Vol. 24. No. 4. pp. 1753-1762.
Cite this
RIS
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TY - JOUR
DO - 10.1007/s00044-014-1262-z
UR - https://doi.org/10.1007/s00044-014-1262-z
TI - Modification of 3,5-bis(arylidene)-4-piperidone pharmacophore by phosphonate group using 1,2,3-triazole cycle as a linker for the synthesis of new cytostatics
T2 - Medicinal Chemistry Research
AU - Makarov, Mikhail V.
AU - Rybalkina, Ekaterina Yu
AU - Khrustalev, Victor N.
AU - Röschenthaler, Gerd-Volker
PY - 2014
DA - 2014/09/20
PB - Springer Nature
SP - 1753-1762
IS - 4
VL - 24
SN - 1054-2523
SN - 1554-8120
ER -
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BibTex (up to 50 authors)
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@article{2014_Makarov,
author = {Mikhail V. Makarov and Ekaterina Yu Rybalkina and Victor N. Khrustalev and Gerd-Volker Röschenthaler},
title = {Modification of 3,5-bis(arylidene)-4-piperidone pharmacophore by phosphonate group using 1,2,3-triazole cycle as a linker for the synthesis of new cytostatics},
journal = {Medicinal Chemistry Research},
year = {2014},
volume = {24},
publisher = {Springer Nature},
month = {sep},
url = {https://doi.org/10.1007/s00044-014-1262-z},
number = {4},
pages = {1753--1762},
doi = {10.1007/s00044-014-1262-z}
}
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MLA
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Makarov, Mikhail V., et al. “Modification of 3,5-bis(arylidene)-4-piperidone pharmacophore by phosphonate group using 1,2,3-triazole cycle as a linker for the synthesis of new cytostatics.” Medicinal Chemistry Research, vol. 24, no. 4, Sep. 2014, pp. 1753-1762. https://doi.org/10.1007/s00044-014-1262-z.