Synthesis and Pharmacological Properties of 4‐Methyl‐1‐(methylsulfinylmethyl)‐7‐thiabicyclo[3.3.1]non‐3‐en‐2‐one 7‐Oxide.

Ulendeeva, A. D.; Никитина, Т. С.; Баева, Л. А.; Спирихин, Л. В.; Karachurina, L. T.; Khisamutdinova, R. Yu.; Makara, N. S.; Zarudii, F. S.; Lyapina, N. K.

doi:10.1002/chin.200523173

Cited by 3 publications

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“…17 In the case of a sulfide with a pyrazole substituent, a sulfoxide is also formed in good yield; no oxidation products at nitrogen atoms were found. Disulfide 13 (Scheme 4 ) is oxidized by 1a with the formation of bis-sulfoxide (it has antiarrhythmic activity) 18a as at the equimolar ratio of the reactants and with an excess of substrate of 1:2. The bis-sulfoxide precipitates as colorless needles from benzene during the reaction.…”

Section: Table 1 Dependence Of the Sulfoxide Yield On C...mentioning

confidence: 99%

Catalyst-Free Oxidation of Sulfides to Sulfoxides by gem-Dihydroperoxide under Mild Conditions

Grabovskii¹,

Andriyashina²,

Лобов³

et al. 2023

Synlett

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Section: Table 1 Dependence Of the Sulfoxide Yield On C...mentioning

confidence: 99%

Catalyst-Free Oxidation of Sulfides to Sulfoxides by gem-Dihydroperoxide under Mild Conditions

Grabovskii¹,

Andriyashina²,

Лобов³

et al. 2023

Synlett

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“…Ketosulfides are of interest as corrosion inhibitors [1,2], growth stimulators of agricultural crops [3], and synthesis of biologically active compounds [4,5]. One of the convenient ways to obtain ketosulfides is the addition of thiols to unsaturated ketones by the Michael reaction.…”

Section: Introductionmentioning

confidence: 99%

SYNTHESIS OF Β-Ketosulfides BASED ON BENZALACETONE AND RESEARCH INTO THEIR INHIBITORY PROPERTIES

Kyazimov,

Guseynov,

Madji

et al. 2023

Chemical Problems

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The interaction of benzalacetone with mercaptoacetic acid and its alkyl esters was used to synthesize and characterize new representatives of β-ketosulfides, the structure of which was proved by 1H and 13С NMR- spectroscopy. The gravimetric method was used to study the influence of the synthesized compounds on the corrosion rate of St-3 in various aggressive medium. It was established that the studied compounds inhibit the corrosion process both in single-phase acidic (0.1N HCl и 0.1N H2SO4), and in twophase (electrolyte-hydrocarbon) media. In the latter case, they are more effective - the corrosion rate of St-3 decreases from 2.1 to 0.06-0.35 g/m 2 hour, while the degree of protection against corrosion is 83.3-97.1 %. The studied compounds exhibit a greater protective effect in hydrochloric acid solution (97.1-92.45%), than in sulfuric acid (76.9-87.1%). Among the tested compounds, β-ketosulfide obtained on the basis of mercaptoacetic acid showed the highest inhibitory efficiency in both mediums.

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“…Compound I may be regarded as sulfur-containing analog of physiologically active 3-and 7-azabicyclo[3.3.1]nonanes which constitute a structural fragment of molecules of many natural alkaloids [2][3][4]. Bis-sulfoxide [5] derived from compound I exhibits antiphlogistic and antiarrhythmic activity in combination with low toxicity [6]. Studies on transformations of thiabicyclonon-7-en-6-one I could extend the series of potential biologically active substances that can be prepared from accessible natural starting compounds, such as hydrogen sulfide, petroleum thiols, and gas condensate.…”

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confidence: 99%

Reactions of 8-methyl-5-methylsulfanylmethyl-3-thiabicyclo-[3.3.1]non-7-en-6-one at the carbonyl group

et al. 2010

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The reduction of 8-methyl-5-methylsulfanylmethyl-3-thiabicyclo[3.3.1]non-7-en-6-one with aluminum hydride, lithium tetrahydridoaluminate, or lithium tris(tert-butoxy)hydridoaluminate in tetrahydrofuran gave 8-methyl-5-methylsulfanylmethyl-3-thiabicyclo[3.3.1]non-7-en-6-ol. 8-Methyl-5-methylsulfanylmethyl-3-thiabicyclo[3.3.1]nonan-6-ol was obtained by reduction of the title compound with sodium tetrahydridoborate in pyridine or dimethylformamide. The reaction of 8-methyl-5-methylsulfanylmethyl-3-thiabicyclo[3.3.1]non-7-en-6-one with hydroxylamine hydrochloride afforded the corresponding oxime.8-Methyl-5-methylsulfanylmethyl-3-thiabicyclo-[3.3.1]non-7-en-6-one (I) is the condensation product of sodium sulfide, sodium methanethiolate, formaldehyde, and acetone [1]. Compound I may be regarded as sulfur-containing analog of physiologically active 3-and 7-azabicyclo[3.3.1]nonanes which constitute a structural fragment of molecules of many natural alkaloids [2][3][4]. Bis-sulfoxide [5] derived from compound I exhibits antiphlogistic and antiarrhythmic activity in combination with low toxicity [6]. Studies on transformations of thiabicyclonon-7-en-6-one I could extend the series of potential biologically active substances that can be prepared from accessible natural starting compounds, such as hydrogen sulfide, petroleum thiols, and gas condensate.We previously [5] studied oxidation of thiabicyclonon-7-en-6-one I at the sulfur atoms. In the present article we describe the reduction of the carbonyl group in compound I with aluminum hydride, lithium tetrahydridoaluminate, and lithium tris(tert-butoxy)hydridoaluminate in tetrahydrofuran, and with sodium tetrahydridoborate in ethanol, methanol, methanol-THF, pyridine, and DMF; also, reactions of bicyclic enone I with glycerol, ethylene glycol, ethane-1,2-dithiol, 2-sulfanylethanol, and hydroxylamine hydrochloride were studied.Reduction of α,β-unsaturated ketones with sodium tetrahydridoborate, lithium tetrahydridoaluminate, and complex hydrides derived therefrom is known to result in the formation of the corresponding allyl alcohol, saturated ketone, or saturated alcohol, depending on the reducing agent, substrate nature, and reaction conditions [7]. Selective reduction of the carbonyl group in thiabicyclonon-7-en-6-one I, the double bond remaining intact, was achieved using lithium tetrahydridoaluminate, as well as aluminum hydride or lithium tris(tert-butoxy)hydridoaluminate (generated in situ from lithium tetrahydridoaluminate and aluminum chloride or tert-butyl alcohol, respectively), in tetrahydrofuran (Scheme 1). The yield of allyl alcohol II was 79, 88, and 90%, respectively.Treatment of compound I with 4 equiv of sodium tetrahydridoborate in pyridine or dimethylformamide resulted in the reduction of both carbonyl group and double bond, and the yield of saturated alcohol III was almost quantitative (96 and 98%, respectively). Selective formation of alcohol III was also observed in the reaction with 1 equiv of sodium tetrahydridoborate; however, the conversion of initi...

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Synthesis and Pharmacological Properties of 4‐Methyl‐1‐(methylsulfinylmethyl)‐7‐thiabicyclo[3.3.1]non‐3‐en‐2‐one 7‐Oxide.

Cited by 3 publications

References 0 publications

Catalyst-Free Oxidation of Sulfides to Sulfoxides by gem-Dihydroperoxide under Mild Conditions

Catalyst-Free Oxidation of Sulfides to Sulfoxides by gem-Dihydroperoxide under Mild Conditions

SYNTHESIS OF Β-Ketosulfides BASED ON BENZALACETONE AND RESEARCH INTO THEIR INHIBITORY PROPERTIES

Reactions of 8-methyl-5-methylsulfanylmethyl-3-thiabicyclo-[3.3.1]non-7-en-6-one at the carbonyl group

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