Open Access
Replacing the phthalimide core in thalidomide with benzotriazole
Mikhail Krasavin
1
,
Andrey Bubyrev
1
,
Alexander Kazantsev
1
,
Christopher Heim
2
,
Samuel Maiwald
2
,
Daniil Zhukovsky
1
,
Dmitry Darin
1
,
Publication type: Journal Article
Publication date: 2022-02-28
scimago Q2
wos Q1
SJR: 0.857
CiteScore: 11.2
Impact factor: 5.4
ISSN: 14756366, 14756374
PubMed ID:
35220840
Drug Discovery
General Medicine
Pharmacology
Abstract
Abstract The advent of proteolysis-targeting chimaeras (PROTACs) mandates that new ligands for the recruitment of E3 ligases are discovered. The traditional immunomodulatory drugs (IMiDs) such as thalidomide and its analogues (all based on the phthalimide glutarimide core) bind to Cereblon, the substrate receptor of the CRL4ACRBN E3 ligase. We designed a thalidomide analogue in which the phthalimide moiety was replaced with benzotriazole, using an innovative synthesis strategy. Compared to thalidomide, the resulting “benzotriazolo thalidomide” has a similar binding mode, but improved properties, as revealed in crystallographic analyses, affinity assays and cell culture.
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Metrics
13
Total citations:
13
Citations from 2024:
5
(38%)
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MLA
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GOST
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Krasavin M. et al. Replacing the phthalimide core in thalidomide with benzotriazole // Journal of Enzyme Inhibition and Medicinal Chemistry. 2022. Vol. 37. No. 1. pp. 527-530.
GOST all authors (up to 50)
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Krasavin M., Bubyrev A., Kazantsev A., Heim C., Maiwald S., Zhukovsky D., Darin D., Hartmann M. D., Bunev A. Replacing the phthalimide core in thalidomide with benzotriazole // Journal of Enzyme Inhibition and Medicinal Chemistry. 2022. Vol. 37. No. 1. pp. 527-530.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1080/14756366.2021.2024525
UR - https://doi.org/10.1080/14756366.2021.2024525
TI - Replacing the phthalimide core in thalidomide with benzotriazole
T2 - Journal of Enzyme Inhibition and Medicinal Chemistry
AU - Krasavin, Mikhail
AU - Bubyrev, Andrey
AU - Kazantsev, Alexander
AU - Heim, Christopher
AU - Maiwald, Samuel
AU - Zhukovsky, Daniil
AU - Darin, Dmitry
AU - Hartmann, Marcus D.
AU - Bunev, Alexander
PY - 2022
DA - 2022/02/28
PB - Taylor & Francis
SP - 527-530
IS - 1
VL - 37
PMID - 35220840
SN - 1475-6366
SN - 1475-6374
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2022_Krasavin,
author = {Mikhail Krasavin and Andrey Bubyrev and Alexander Kazantsev and Christopher Heim and Samuel Maiwald and Daniil Zhukovsky and Dmitry Darin and Marcus D. Hartmann and Alexander Bunev},
title = {Replacing the phthalimide core in thalidomide with benzotriazole},
journal = {Journal of Enzyme Inhibition and Medicinal Chemistry},
year = {2022},
volume = {37},
publisher = {Taylor & Francis},
month = {feb},
url = {https://doi.org/10.1080/14756366.2021.2024525},
number = {1},
pages = {527--530},
doi = {10.1080/14756366.2021.2024525}
}
Cite this
MLA
Copy
Krasavin, Mikhail, et al. “Replacing the phthalimide core in thalidomide with benzotriazole.” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 37, no. 1, Feb. 2022, pp. 527-530. https://doi.org/10.1080/14756366.2021.2024525.