Biological activity of sulfoxides and sulfones

Kalir, A.; Kalir, Henry H.

doi:10.1002/9780470034408.ch16

Cited by 20 publications

(5 citation statements)

References 57 publications

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“…[3] Prominent examples are the sulfinyl-substituted benzimidazoles which are proton pump inhibitors (PPIs), a powerful class of anti-ulcer agents. [4] Until recently the leading molecule of this family was omeprazole.…”

Section: Introductionmentioning

confidence: 99%

Applications of Catalytic Asymmetric Sulfide Oxidations to the Syntheses of Biologically Active Sulfoxides

Legros

Dehli

Bolm

2005

Advanced Synthesis & Catalysis

426

169

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Optically active sulfoxides are important compounds for medicinal and pharmaceutical chemistry. Driven by the increasing demand for efficient, selective and environmentally friendly industrial processes, several catalytic methodologies have been developed in recent years for the stereoselective oxidation of sulfides for the preparation of biologically active sulfoxides. Both small-scale approaches to the problem as well as some large-scale applications that are already in industrial use are described in this review.

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Section: Introductionmentioning

confidence: 99%

Applications of Catalytic Asymmetric Sulfide Oxidations to the Syntheses of Biologically Active Sulfoxides

Legros

Dehli

Bolm

2005

Advanced Synthesis & Catalysis

426

169

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“…An excellent aprotic solvent (DMSO) has been intensively studied for its pharmacological activity, as it has many effects. For example, it has been found to alleviate the symptoms of arthritis, secondary amyloidosis associated with rheumatoid arthritis, bursitis, and myositis [16]. Semipolar sulfur-oxygen bonds in DMSO have a full or partial positive charge on sulfur and a negative charge on the oxygen atom.…”

Section: Introductionmentioning

confidence: 99%

An Experimental Study on the Solubility of Betulin in the Complex Solvent Ethanol-DMSO

Shambilova,

Bukanova,

Kalauova

et al. 2024

Processes

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Betulin is a promising natural organic substance due to its antibacterial, fungicidal, and antitumor properties, as are their derivatives. The particle size of betulin can reach several tens of micrometers, and its thickness is several microns. There are various ways of processing betulin, but the most promising are solution methods (applying thin layers, impregnation, etc.). Application or impregnation of various materials is carried out using betulin; however, currently known solvents do not allow obtaining solutions with the necessary content of it. Since a number of direct solvents are already known for betulin, which provides only low-concentration solutions, the use of complex systems based on two solvents can become the optimal solution to the problem. The literature data show that the use of mixtures of solvents allows for the preparation of homogeneous solutions, for example, for natural polymers like cellulose, etc. This approach to obtaining solutions has become the basis for the processing of betulin. The use of a mixed solvent based on ethanol and DMSO for the preparation of betulin solutions has been proposed for the first time. The solubility of betulin in a mixture system with a ratio of components of 50 wt.% to 50 wt.% was studied, and a solubility curve was plotted. It is shown that the use of a two-component solvent makes it possible to transfer up to 10% of betulin into solution, which is almost twice as much as compared to already known solvents. The rheological properties of the obtained solutions have been studied. The viscosity of betulin solutions in a complex solvent depends on its content and temperature, so for 7% solutions at 70 °C, it is approximately 0.008 Pa*s. Applying betulin to the surface of the cardboard increases its hydrophobic properties and repellency.

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“…Sulfoxides have many chemical and industrial uses, and they have also attracted considerable attention because of their significant biological and pharmacological importance. Because the stereochemistry of the sulfur atom of a sulfoxide molecule significantly affects its biological activities, the stereoselective synthesis of sulfoxides has become increasingly more relevant.…”

Section: Introductionmentioning

confidence: 99%

Efficient and Stereoselective Syntheses of Isomerically Pure 4-Aminotetrahydro-2H-thiopyran 1-Oxide Derivatives

Mizojiri

Takami

Itô

et al. 2017

Org. Process Res. Dev.

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Efficient and stereoselective syntheses of isomerically pure 4-aminotetrahydro-2H-thiopyran 1-oxide derivatives have successfully been achieved. Isomerically pure (4-nitrophenyl)sulfonyltetrahydro-2H-thiopyran 1-oxides were identified by X-ray crystallographic analyses, and isomerically pure sulfoxide derivatives were characterized by 1H NMR. An oxidation reaction of tert-butyl(4-nitrophenyl)sulfonyl(tetrahydro-2H-thiopyran-4-yl)carbamate with Oxone provided steric control, affording its trans sulfoxide with high efficiency and selectivity. From the obtained trans sulfoxide derivatives, cis sulfoxide derivatives were synthesized conveniently by a hydrogen chloride catalyzed isomerization.

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Biological activity of sulfoxides and sulfones

Cited by 20 publications

References 57 publications

Applications of Catalytic Asymmetric Sulfide Oxidations to the Syntheses of Biologically Active Sulfoxides

Applications of Catalytic Asymmetric Sulfide Oxidations to the Syntheses of Biologically Active Sulfoxides

An Experimental Study on the Solubility of Betulin in the Complex Solvent Ethanol-DMSO

Efficient and Stereoselective Syntheses of Isomerically Pure 4-Aminotetrahydro-2H-thiopyran 1-Oxide Derivatives

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