Syn-Propanethial S-Oxide as an Available Natural Building Block for the Preparation of Nitro-Functionalized, Sulfur-Containing Five-Membered Heterocycles: An MEDT Study

Autor:	Mikołaj Sadowski, Ewa Dresler, Karolina Zawadzińska, Aneta Wróblewska, Radomir Jasiński
Jazyk:	angličtina
Rok vydání:	2024
Předmět:	[3 + 2] cycloaddition oxathiolanes propanethial S-oxide nitroalkenes MEDT ELF Organic chemistry QD241-441
Zdroj:	Molecules, Vol 29, Iss 20, p 4892 (2024)
Druh dokumentu:	article
ISSN:	1420-3049
DOI:	10.3390/molecules29204892
Popis:	The regio- and stereoselectivity and the molecular mechanisms of the [3 + 2] cycloaddition reactions between Syn-propanethial S-oxide and selected conjugated nitroalkenes were explored theoretically in the framework of the Molecular Electron Density Theory. It was found that cycloadditions with the participation of nitroethene as well as its methyl- and chloro-substituted analogs can be realized via a single-step mechanism. On the other hand, [3 + 2] cycloaddition reactions between Syn-propanethial S-oxide and 1,1-dinitroethene can proceed according to a stepwise mechanism with a zwitterionic intermediate. Finally, we evaluated the affinity of model reaction products for several target proteins: cytochrome P450 14α-sterol demethylase CYP51 (RSCB Database PDB ID: 1EA1), metalloproteinase gelatinase B (MMP-9; PDB ID: 4XCT), and the inhibitors of cyclooxygenase COX-1 (PDB:3KK6) and COX-2 (PDB:5KIR).
Databáze:	Directory of Open Access Journals
Externí odkaz:	https://doaj.org/article/e835881cb08f40a6b46d58f9d492d138 Zobrazit plný text záznamu View record in DOAJ Plný text ve formátu PDF Plný text ve formátu HTML
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