M. Adamchik, A. Bubyrev, D. Zhukovsky, P. Zhmurov, A. Bunev, M. Krasavin, “Synthesis of novel glutarimide derivatives <i>via</i> the Michael addition of (hetero)aromatic thiols: pronounced effect of sulfur oxidation on cytotoxicity towards multiple myeloma cell lines”, Mendeleev Commun., 2023, Volume 33, Issue 1,Pages <nobr>67

This article is cited in 1 paper

Communications

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

M. Adamchik^a, A. Bubyrev^a, D. Zhukovsky^a, P. Zhmurov^a, A. Bunev^b, M. Krasavin^ac

^a Institute of Chemistry, St. Petersburg State University, St. Petersburg, Russian Federation
^b Medicinal Chemistry Centre, Togliatti State University, Togliatti, Russian Federation
^c Immanuel Kant Baltic Federal University, Kaliningrad, Russian Federation

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.

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

Language: English

DOI: 10.1016/j.mencom.2023.01.021

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