Sulfur‐containing derivatives of 1,4‐naphthoquinone, part 2: Sulfenyl derivative synthesis

Stasevych, Maryna; Plotnikov, Maxym Yu.; Platonov, Mykola O.; Sabat, Svitlana I.; Musyanovych, Rostyslav Ya.; Novikov, Volodymyr

doi:10.1002/hc.20157

Cited by 6 publications

(8 citation statements)

References 14 publications

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“…Compared to 2-(2,6-di-tert-butyl-4-hydroxyphenyl)-3-sulfenylchloride-1,4-naphthoquinone a peak of hydroxyl-group in 1 H NMR spectrum and ІR of the compound (5а) is absent [52].…”

Section: Resultsmentioning

confidence: 94%

“…In this work addition and elimination reactions of sulfenyl chlorides [52] with the formation of corresponding sulfides and thiocyclic compounds were carried out.…”

Section: Resultsmentioning

confidence: 99%

“…As it is known that the formation of thioketones can take place in the elimination reactions [50] and with the purpose of synthesis of new thioketones on the basis of substitutes 1,4-naphthoquinone the reactions of 2-hydroxy-1g and 2-(2,3-di-tert-butyl-4-hydroxyphenyl)-3-sulfenylchloride-1,4-naphthoquinone 1а [52] with a triethylamine were carried out and the reaction products were investigated (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

“…In view of the special importance of derivatives of 1,4-naphthoquinone and thiocontaining compounds the interest in the researches of the synthesis of new sulfides derivatives of 1,4-naphthoquinone is obvious. The synthesis of new asymmetrical sulfides of 2-substituted-1,4naphthoquinones with different pharmacophore groups on the basis of the reactions of addition of early obtained sulfenyl chlorides of 1,4-naphthoquinone [52] as well as investigation of thioketones formation and their interaction with unsaturated compounds is the continuation of the researches at the Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology.…”

Section: Introductionmentioning

confidence: 99%

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Reactions of Sulfenyl Chlorides of Substituted 1,4-Naphthoquinone

Musyanovych¹

2011

ChChT

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“…Compared to 2-(2,6-di-tert-butyl-4-hydroxyphenyl)-3-sulfenylchloride-1,4-naphthoquinone a peak of hydroxyl-group in 1 H NMR spectrum and ІR of the compound (5а) is absent [52].…”

Section: Resultsmentioning

confidence: 94%

“…In this work addition and elimination reactions of sulfenyl chlorides [52] with the formation of corresponding sulfides and thiocyclic compounds were carried out.…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Reactions of Sulfenyl Chlorides of Substituted 1,4-Naphthoquinone

Musyanovych¹

2011

ChChT

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“…Prior work by others with small molecules containing sulfenamide bonds demonstrated that they were readily synthesized and possessed reasonable stabilities. 35,42–44 Molecules with sulfenamide bonds degraded into radicals at elevated temperatures which led to their applications as vulcanizing agents in the rubber industry. 26–28 Based on their properties as protecting groups for amines, it was known that sulfenamides were stable under neutral and basic conditions, but could be cleaved under acidic conditions.…”

Section: Introductionmentioning

confidence: 99%

New Class of Biodegradable Polymers Formed from Reactions of an Inorganic Functional Group

et al. 2012

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Although numerous small molecules have been synthesized with sulfenamide bonds (R2N-SR), this is the first report of the synthesis of polysulfenamides. These polymers are readily synthesized at room temperature using secondary diamines and dithiosuccinimides. The dithiosuccinimides were readily synthesized in one step by the reaction of dithiols such as HS(CH2)6SH with N-chlorosuccinimide. The resulting dithiosuccinimides were either recrystallized or readily purified by chromatography on silica gel and required no special handling. The conversions of polymerization ranged from 95 to 98%, and the molecular weights of the polymer reached as high as 6,300 g mol−1. The sulfenamide bond was very stable in organic solvents, and no degradation was observed under atmospheric conditions in C6D6 for 30 days. In contrast, the sulfenamide bond readily decomposed in less than 12 h in D2O. Polysulfenamides were fabricated into micron-sized particles loaded with dye and endocytosed into JAWSII immature dendritic and HEK293 cells. Polysulfenamides represent a new class of polymers that are readily synthesized, stable in aprotic solvents, and readily degrade in water.

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