Home / Publications / Synthesis of novel glutarimide derivatives via the Michael addition of (hetero)aromatic thiols: pronounced effect of sulfur oxidation on cytotoxicity towards multiple myeloma cell lines

Synthesis of novel glutarimide derivatives via the Michael addition of (hetero)aromatic thiols: pronounced effect of sulfur oxidation on cytotoxicity towards multiple myeloma cell lines

Maria Aleksandrovna Adamchik 1
Maria Aleksandrovna Adamchik
, 
Andrey Ivanovich Bubyrev 1
Andrey Ivanovich Bubyrev
, 
Daniil Dmitrievich Zhukovsky 1
Daniil Dmitrievich Zhukovsky
, 
Petr Aleksandrovich Zhmurov 1
Petr Aleksandrovich Zhmurov
, 
Alexander Siyasatovich Bunev 2
Alexander Siyasatovich Bunev
, 
Mikhail Yur'evich Krasavin 1, 3
Mikhail Yur'evich Krasavin
1 Institute of Chemistry, St. Petersburg State University, St. Petersburg, Russian Federation
2 Medicinal Chemistry Centre, Togliatti State University, Togliatti, Russian Federation
3 Immanuel Kant Baltic Federal University, Kaliningrad, Russian Federation
10.1016/j.mencom.2023.01.021
Published 2022-12-26
Communication , Volume 33, Issue 1, 67-69
1
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Adamchik M. A. et al. Synthesis of novel glutarimide derivatives via the Michael addition of (hetero)aromatic thiols: pronounced effect of sulfur oxidation on cytotoxicity towards multiple myeloma cell lines // Mendeleev Communications. 2022. Vol. 33. No. 1. pp. 67-69.
GOST all authors (up to 50) Copy
Adamchik M. A., Bubyrev A. I., Zhukovsky D. D., Zhmurov P. A., Bunev A. S., Krasavin M. Y. Synthesis of novel glutarimide derivatives via the Michael addition of (hetero)aromatic thiols: pronounced effect of sulfur oxidation on cytotoxicity towards multiple myeloma cell lines // Mendeleev Communications. 2022. Vol. 33. No. 1. pp. 67-69.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2023.01.021
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.021
TI - Synthesis of novel glutarimide derivatives via the Michael addition of (hetero)aromatic thiols: pronounced effect of sulfur oxidation on cytotoxicity towards multiple myeloma cell lines
T2 - Mendeleev Communications
AU - Adamchik, Maria Aleksandrovna
AU - Bubyrev, Andrey Ivanovich
AU - Zhukovsky, Daniil Dmitrievich
AU - Zhmurov, Petr Aleksandrovich
AU - Bunev, Alexander Siyasatovich
AU - Krasavin, Mikhail Yur'evich
PY - 2022
DA - 2022/12/26
PB - Mendeleev Communications
SP - 67-69
IS - 1
VL - 33
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2022_Adamchik,
author = {Maria Aleksandrovna Adamchik and Andrey Ivanovich Bubyrev and Daniil Dmitrievich Zhukovsky and Petr Aleksandrovich Zhmurov and Alexander Siyasatovich Bunev and Mikhail Yur'evich Krasavin},
title = {Synthesis of novel glutarimide derivatives via the Michael addition of (hetero)aromatic thiols: pronounced effect of sulfur oxidation on cytotoxicity towards multiple myeloma cell lines},
journal = {Mendeleev Communications},
year = {2022},
volume = {33},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.021},
number = {1},
pages = {67--69},
doi = {10.1016/j.mencom.2023.01.021}
}
MLA
Cite this
MLA Copy
Adamchik, Maria Aleksandrovna, et al. “Synthesis of novel glutarimide derivatives via the Michael addition of (hetero)aromatic thiols: pronounced effect of sulfur oxidation on cytotoxicity towards multiple myeloma cell lines.” Mendeleev Communications, vol. 33, no. 1, Dec. 2022, pp. 67-69. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.021.
Views
1

Keywords

2-aminoglutarimide
Cereblon
cytotoxicity
hydrogen bonding
multiple myeloma.
Oxone® oxidation
stronger binding
sulfones
thio-Michael reaction

Abstract

2-Methylidenepiperidine-2,6-dione was employed as a substrate in the thio-Michael addition of a series of (hetero)-aromatic thiols. Oxidation of the resulting (hetero)arylthio derivatives with Oxone® gave the corresponding sulfones. Testing of the latter against multiple myeloma cell lines MOLP-8 and KMS-12-PE alongside with selected precursor sulfides confirmed the earlier observed significantly higher cytotoxicity of sulfones.

References

.
Replacing the phthalimide core in thalidomide with benzotriazole
Krasavin M., Bubyrev A., Kazantsev A., Heim C., Maiwald S., Zhukovsky D., Dar’in D., Hartmann M.D., Bunev A.
Journal of Enzyme Inhibition and Medicinal Chemistry, 2022
.
Sweet and Blind Spots in E3 Ligase Ligand Space Revealed by a Thermophoresis-Based Assay
Maiwald S., Heim C., Hernandez Alvarez B., Hartmann M.D.
ACS Medicinal Chemistry Letters, 2020
.
Induction of CD28 on the new myeloma cell line MOLP-8 with t(11;14)(q13;q32) expressing δ/λ type immunoglobulin
Matsuo Y., Drexler H.G., Harashima A., Okochi A., Hasegawa A., Kojima K., Orita K.
Leukemia Research, 2004
.
Bivalent Ligands for Protein Degradation in Drug Discovery
Scheepstra M., Hekking K.F., van Hijfte L., Folmer R.H.
Computational and Structural Biotechnology Journal, 2019
.
E3 Ligase Ligands in Successful PROTACs: An Overview of Syntheses and Linker Attachment Points
Bricelj A., Steinebach C., Kuchta R., Gütschow M., Sosič I.
Frontiers in Chemistry, 2021
.
Structure of the DDB1–CRBN E3 ubiquitin ligase in complex with thalidomide
Fischer E.S., Böhm K., Lydeard J.R., Yang H., Stadler M.B., Cavadini S., Nagel J., Serluca F., Acker V., Lingaraju G.M., Tichkule R.B., Schebesta M., Forrester W.C., Schirle M., Hassiepen U., et. al.
Nature, 2014
.
Ligands for cereblon: 2017–2021 patent overview
Kazantsev A., Krasavin M.
Expert Opinion on Therapeutic Patents, 2021
.
PROTAC targeted protein degraders: the past is prologue
Békés M., Langley D.R., Crews C.M.
Nature Reviews Drug Discovery, 2022
.
Chemical Ligand Space of Cereblon
Boichenko I., Bär K., Deiss S., Heim C., Albrecht R., Lupas A.N., Hernandez Alvarez B., Hartmann M.D.
ACS Omega, 2018
.
Lenalidomide Causes Selective Degradation of IKZF1 and IKZF3 in Multiple Myeloma Cells
Krönke J., Udeshi N.D., Narla A., Grauman P., Hurst S.N., McConkey M., Svinkina T., Heckl D., Comer E., Li X., Ciarlo C., Hartman E., Munshi N., Schenone M., Schreiber S.L., et. al.
Science, 2014
.
Mechanism of action of immunomodulatory drugs (IMiDS) in multiple myeloma
Quach H., Ritchie D., Stewart A.K., Neeson P., Harrison S., Smyth M.J., Prince H.M.
Leukemia, 2009
.
Synthesis of novel glutarimide ligands for the E3 ligase substrate receptor Cereblon (CRBN): Investigation of their binding mode and antiproliferative effects against myeloma cell lines
Krasavin M., Adamchik M., Bubyrev A., Heim C., Maiwald S., Zhukovsky D., Zhmurov P., Bunev A., Hartmann M.D.
European Journal of Medicinal Chemistry, 2023