1,2-Benzoxathiin-4(3H)-one 2,2-dioxide – an underinvestigated building block with a high synthetic and pharmacological potential: synthesis, chemical properties, biological activity

Authors

DOI:

https://doi.org/10.24959/ophcj.21.234271

Keywords:

sultone; oxathiine; heterocyclization; active methylene ketones; biological activity

Abstract

Aim. To analyze the available literature data on the methods of synthesis, chemical transformations and the biological activity of derivatives containing a sultone core – 1,2-benzoxathiin-4(3H)-one 2,2-dioxide – and to show the possibilities of their further use in the construction of new molecular systems with attractive pharmacological properties.

Results and discussion. The most widespread method for the synthesis of 1,2-benzoxathiin-4(3H)-one 2,2-dioxides is the cyclization of salicylic acid derivatives. The known chemical transformations of 1,2-benzoxathiin-4(3H)-one 2,2-dioxides deal with all reaction centers of the heterocyclic fragment of the condensed system – C=O and CH2 groups, SO2–O bond, CH2CO fragment as a whole. It should be noted that the oxathiine nucleus is prone to undergo recyclizations. The use of 1,2-benzoxathiin-4(3H)-one 2,2-dioxides in multicomponent transformations still remains hardly explored. The “abnormal” course of some classical transformations involving 1,2-benzoxathiine 2,2-dioxides is also noteworthy. The study of the pharmacological properties of 1,2-benzoxathiin-4(3H)-one 2,2-dioxide derivatives is scarce and mainly based on their structural similarity to the coumarin core, which led to the study of anticoagulant, antimicrobial and antitumor properties for the sultone derivatives.

Conclusions. The analysis has shown a limited number of studies in each aspect – approaches to the synthesis of 1,2-benzoxathiin-4(3H)-one 2,2-dioxides, their chemical transformations and the study of their pharmacological activity. In addition to a small number of publications on this heterocyclic system, there have been almost no sultone studies in the last 20 years. Taking this into account 1,2-benzoxathiin-4(3H)-one 2,2-dioxide and its derivatives deserve close attention as objects of research for experimental chemistry and pharmacology.

Supporting Agency

  • The work is a part of researches of the National University of Pharmacy on the topic «Organic synthesis and analysis of biologically active compounds, drugs development on the basis of synthetic substances» (the state registration No. 01144000943; the research period 2019 – 2024)

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2021-06-23

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Hryhoriv, H. V.; Lega, D. A.; Shemchuk, L. A. 1,2-Benzoxathiin-4(3H)-One 2,2-Dioxide – an Underinvestigated Building Block With a High Synthetic and Pharmacological Potential: Synthesis, Chemical Properties, Biological Activity. J. Org. Pharm. Chem. 2021, 19, 4-28.

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Vol. 19 No. 2(74) (2021)

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