Effects of 2-(substituted-sulfanyl)-3,5-dihydro-imidazole-4-one and 2-(substituted-sulfanyl)-1H-imidazole-4,5-dione derivatives on serum HDL-cholesterol

Elokdah, Hassan; Sulkowski, Theodore S.; Cochran, David; McKean, Mar-Lee; Quinet, Elaine

doi:10.1016/s0960-894x(00)00338-3

Cited by 8 publications

(7 citation statements)

References 4 publications

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“…Notable is the reaction of methyl isocyanoacetate ( 3 e ), which features an acidic methylene functionality (Table 3, entry 6). When two methyl groups were present at the α‐position of this isocyanide (substrate 3 k ), 7 was isolated in high yield (Table 3, entry 17) 23. Compound 7 is formed from the initial reaction product 5 q by lactamization (Thorpe–Ingold).…”

Section: Methodsmentioning

confidence: 99%

Sustainable Three‐Component Synthesis of Isothioureas from Isocyanides, Thiosulfonates, and Amines

et al. 2014

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Multiple applications of isothioureas as fine chemicals (or their precursors) are known, but a general sustainable method for their synthesis was hitherto unavailable. We report a novel general approach towards S-alkyl and S-aryl isothioureas through a copper(I)-catalyzed three-component reaction between amines, isocyanides, and thiosulfonates. The formal synthesis of a superpotent sweetener further illustrates the applicability of our method.

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Section: Methodsmentioning

confidence: 99%

Sustainable Three‐Component Synthesis of Isothioureas from Isocyanides, Thiosulfonates, and Amines

et al. 2014

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“…In vivo profiling of a series of 2-substituted sulfanyl-3,5-dihydroimidazol-4-one derivatives ( 1 ) disclosed their preferential activity for increasing HDL cholesterol relative to the other lipoprotein fractions as reported earlier (Chart ) . Issues concerning the chemical and metabolic stability of this class of compounds led to the design and evaluation of a related series of substituted 2-thioxoimidazolidin-4-one (thiohydantoin) derivatives 2 and 3 .…”

Section: Introductionmentioning

confidence: 60%

“…Earlier published work identified 2-ethylsulfanylimidazolone ( 1 ) as a potential biological lead exhibiting HDL-C elevating properties in several animal models …”

Section: Discussionmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Thio-Containing Compounds with Serum HDL-Cholesterol-Elevating Properties

Elokdah¹,

Sulkowski²,

Abou‐Gharbia³

et al. 2003

J. Med. Chem.

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A novel series of substituted sulfanyldihydroimidazolones (1) that modulates high-density lipoprotein cholesterol (HDL-C) has been reported to have HDL-elevating properties in several animal models. Concerns about the chemical and metabolic stability of 1 directed us to explore the structure-activity relationship (SAR) of a related series of substituted thiohydantoins (2). Expansion of the scope of the thiohydantoin series led to exploration of compounds in related thio-containing ring systems 3-7 and the N-cyanoguanidine derivative 8. Compounds were tested sequentially in three animal models to assess their HDL-C elevating efficacy and safety profiles. Further evaluation of selected compounds in a dose-response paradigm culminated in the identification of compound 2.39 as a candidate compound for advanced preclinical studies.

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“…When two methyl groups were present at the aposition of this isocyanide (substrate 3 k), 7 was isolated in high yield (Table 3, entry 17). [23] Compound 7 is formed from the initial reaction product 5 q by lactamization (Thorpe-Ingold). We were pleased to find that aromatic isocyanides were also well tolerated (Table 3, entries 18-20), which is not self-evident because these compounds readily polymerize.…”

Section: Methodsmentioning

confidence: 99%

Sustainable Three‐Component Synthesis of Isothioureas from Isocyanides, Thiosulfonates, and Amines

et al. 2014

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Effects of 2-(substituted-sulfanyl)-3,5-dihydro-imidazole-4-one and 2-(substituted-sulfanyl)-1H-imidazole-4,5-dione derivatives on serum HDL-cholesterol

Cited by 8 publications

References 4 publications

Sustainable Three‐Component Synthesis of Isothioureas from Isocyanides, Thiosulfonates, and Amines

Sustainable Three‐Component Synthesis of Isothioureas from Isocyanides, Thiosulfonates, and Amines

Design, Synthesis, and Biological Evaluation of Thio-Containing Compounds with Serum HDL-Cholesterol-Elevating Properties

Sustainable Three‐Component Synthesis of Isothioureas from Isocyanides, Thiosulfonates, and Amines

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