Open Access
Journal of Enzyme Inhibition and Medicinal Chemistry, volume 37, issue 1, pages 527-530
Replacing the phthalimide core in thalidomide with benzotriazole
Krasavin Mikhail
1
,
Bubyrev Andrey
1
,
Kazantsev Alexander
1
,
Heim Christopher
2
,
Maiwald Samuel
2
,
Zhukovsky Daniil
1
,
Darin Dmitry
1
,
2
Department of Protein Evolution, Max Planck Institute for Developmental Biology, Tübingen, Germany
|
Publication type: Journal Article
Publication date: 2022-02-28
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.6
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.
Citations by journals
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1
2
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European Journal of Medicinal Chemistry
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European Journal of Medicinal Chemistry
2 publications, 22.22%
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Mendeleev Communications
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Mendeleev Communications
2 publications, 22.22%
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Biochemical and Biophysical Research Communications
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Biochemical and Biophysical Research Communications
2 publications, 22.22%
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SSRN Electronic Journal
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SSRN Electronic Journal
1 publication, 11.11%
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Journal of Medicinal Chemistry
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Journal of Medicinal Chemistry
1 publication, 11.11%
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Beilstein Journal of Organic Chemistry
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Beilstein Journal of Organic Chemistry
1 publication, 11.11%
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1
2
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Citations by publishers
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1
2
3
4
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6
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Elsevier
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Elsevier
6 publications, 66.67%
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Social Science Electronic Publishing
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Social Science Electronic Publishing
1 publication, 11.11%
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American Chemical Society (ACS)
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American Chemical Society (ACS)
1 publication, 11.11%
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Beilstein-Institut
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Beilstein-Institut
1 publication, 11.11%
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1
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6
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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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.
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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.
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TY - JOUR
DO - 10.1080/14756366.2021.2024525
UR - https://doi.org/10.1080%2F14756366.2021.2024525
TI - Replacing the phthalimide core in thalidomide with benzotriazole
T2 - Journal of Enzyme Inhibition and Medicinal Chemistry
AU - Krasavin, Mikhail
AU - Bubyrev, Andrey
AU - Maiwald, Samuel
AU - Darin, Dmitry
AU - Hartmann, Marcus D.
AU - Bunev, Alexander
AU - Kazantsev, Alexander
AU - Zhukovsky, Daniil
AU - Heim, Christopher
PY - 2022
DA - 2022/02/28 00:00:00
PB - Taylor & Francis
SP - 527-530
IS - 1
VL - 37
PMID - 35220840
SN - 1475-6366
SN - 1475-6374
ER -
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@article{2022_Krasavin,
author = {Mikhail Krasavin and Andrey Bubyrev and Samuel Maiwald and Dmitry Darin and Marcus D. Hartmann and Alexander Bunev and Alexander Kazantsev and Daniil Zhukovsky and Christopher Heim},
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%2F14756366.2021.2024525},
number = {1},
pages = {527--530},
doi = {10.1080/14756366.2021.2024525}
}
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MLA
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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%2F14756366.2021.2024525.