Dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide – a versatile building block for the synthesis of new thiopyran-based heterocyclic systems

Vitalii A. Palchykov; Roman M. Chabanenko; Valeriy V. Konshin; Victor V. Dotsenko; Sergey G. Krivokolysko; Elena A. Chigorina; Yuriy I. Horak; Roman Z. Lytvyn; Andriy A. Vakhula; Mykola D. Obushak; Alexander V. Mazepa

doi:10.1039/C7NJ03846A

Dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide – a versatile building block for the synthesis of new thiopyran-based heterocyclic systems†

Vitalii A. Palchykov,

*^a Roman M. Chabanenko,^a Valeriy V. Konshin,

^b Victor V. Dotsenko,

^bc Sergey G. Krivokolysko,^b Elena A. Chigorina,

^d Yuriy I. Horak,^e Roman Z. Lytvyn,^e Andriy A. Vakhula,^e Mykola D. Obushak

^e and Alexander V. Mazepa^f

Author affiliations

* Corresponding authors

^a Department of Organic Chemistry, Oles Honchar Dnipro National University, 72 Gagarina Av, 49010 Dnipro, Ukraine
E-mail: palchikoff82@gmail.com

^b Department of Chemistry & High Technologies, Kuban State University, 149 Stavropolskaya St, 350040 Krasnodar, Russian Federation

^c Department of Chemistry, North Caucasus Federal University, 1a Pushkin St, 355009 Stavropol, Russian Federation

^d Federal State Unitary Enterprise “State Scientific Research Institute of Chemical Reagents and High Purity Chemical Substances” (FSUE “IREA”), 3 Bogorodsky val St, 107076 Moscow, Russian Federation

^e Department of Organic Chemistry, Ivan Franko National University of Lviv, 6 Kyryla i Mefodiya St, 79005 Lviv, Ukraine

^f A. V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, 86 Lustdorfskaya Rd, 65080 Odessa, Ukraine

Abstract

Three series of new cyclic sulfones have been prepared by a one-pot multi-component reaction (MCR) starting from the readily available dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide. The in silico screening of the synthesized compounds revealed their high anti-inflammatory, antiarthritic, antiasthmatic and antiallergic potential coupled with the strong probability levels of cystinyl aminopeptidase inhibition. The key structures were confirmed by 2D NMR techniques.

New Journal of Chemistry

Dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide – a versatile building block for the synthesis of new thiopyran-based heterocyclic systems†

Abstract

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Dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide – a versatile building block for the synthesis of new thiopyran-based heterocyclic systems

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