Communications

Substituted 3-aryl-4-nitroisoxazoles as potential blockers of the transport protein GLUT5: molecular design, synthesis and primary biotesting

N. E. Astakhova^a, M. S. Kuzmina^a, D. A. Vasilenko^a, D. A. Shashurin^bc, V. Yu. Vasileva^d, A. V. Sudarikova^d, N. A. Zefirov^a, E. B. Averina^a, V. I. Chubinskiy-Nadezhdin^d, E. R. Milaeva^a, O. S. Medvedev^bc, O. N. Zefirova<sup>a

a</sup> Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation
^b Lomonosov Moscow State University Medical Research and Educational Center, 119991 Moscow, Russian Federation
^c V. N. Smirnov Institute of Experimental Cardiology, E. I. Chazov National Medical Research Center for Cardiology, 121552 Moscow, Russian Federation
^d Institute of Cytology, Russian Academy of Sciences, 194064 St.-Petersburg, Russian Federation

Abstract: The structures of isoxazole-containing cyclovinylogues of the intracellular fructose transporter protein GLUT5 inhibitor, N-(4-methylsulfonyl-2-nitrophenyl)benzo[d][1,3]dioxol-5- amine (MSNBA) were designed. The target substituted 3,4,5-isoxazoles were synthesized using a method for converting isoxazole-containing enamines to nitriles by their treatment with tert-butyl nitrite in the presence of boron trifluoride etherate. Primary bioassay demonstrated the ability of the target compounds to inhibit the proliferation of chronic myelogenous leukemia cells K562 in medium containing fructose or glucose.

Keywords: nitroisoxazoles, N-(4-methylsulfonyl-2-nitrophenyl)benzo[d][1,3]dioxol-5-amine (MSNBA), cyclovinylogues, arenologues, fructose, GLUT5 inhibitors, cytotoxicity, cell line K562.

Received: 10.06.2025
Accepted: 21.07.2025

Language: English

DOI: 10.71267/mencom.7848

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