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Yong-xing Song - One of the best experts on this subject based on the ideXlab platform.
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Asymmetric Construction of Bispiro[oxindole-pyrrolidine-Rhodanine]s via Squaramide-Catalyzed Domino Michael/Mannich [3 + 2] Cycloaddition of Rhodanine Derivatives with N-(2,2,2-Trifluoroethyl)isatin Ketimines.
The Journal of organic chemistry, 2018Co-Authors: Yong-xing SongAbstract:Squaramide-catalyzed asymmetric domino Michael/Mannich [3 + 2] cycloaddition reaction between Rhodanine derivatives and N-(2,2,2-trifluoroethyl)isatin ketimines has been developed to synthesize various bispiro[oxindole-pyrrolidine-Rhodanine]s with good to excellent yields (up to 99%) and excellent stereoselectivities (up to >99% ee and >99:1 dr). The biologically active Rhodanine, oxindole, and pyrrolidine moieties were embedded in these novel bispirocyclic products, which will provide some support for the enrichment of chiral heterocyclic compound databases with potential medical value.
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asymmetric construction of bispiro oxindole pyrrolidine Rhodanine s via squaramide catalyzed domino michael mannich 3 2 cycloaddition of Rhodanine derivatives with n 2 2 2 trifluoroethyl isatin ketimines
Journal of Organic Chemistry, 2018Co-Authors: Yong-xing SongAbstract:Squaramide-catalyzed asymmetric domino Michael/Mannich [3 + 2] cycloaddition reaction between Rhodanine derivatives and N-(2,2,2-trifluoroethyl)isatin ketimines has been developed to synthesize various bispiro[oxindole-pyrrolidine-Rhodanine]s with good to excellent yields (up to 99%) and excellent stereoselectivities (up to >99% ee and >99:1 dr). The biologically active Rhodanine, oxindole, and pyrrolidine moieties were embedded in these novel bispirocyclic products, which will provide some support for the enrichment of chiral heterocyclic compound databases with potential medical value.
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Asymmetric Construction of Bispiro[oxindole-pyrrolidine-Rhodanine]s via Squaramide-Catalyzed Domino Michael/Mannich [3 + 2] Cycloaddition of Rhodanine Derivatives with N‑(2,2,2-Trifluoroethyl)isatin Ketimines
2018Co-Authors: Yong-xing SongAbstract:Squaramide-catalyzed asymmetric domino Michael/Mannich [3 + 2] cycloaddition reaction between Rhodanine derivatives and N-(2,2,2-trifluoroethyl)isatin ketimines has been developed to synthesize various bispiro[oxindole-pyrrolidine-Rhodanine]s with good to excellent yields (up to 99%) and excellent stereoselectivities (up to >99% ee and >99:1 dr). The biologically active Rhodanine, oxindole, and pyrrolidine moieties were embedded in these novel bispirocyclic products, which will provide some support for the enrichment of chiral heterocyclic compound databases with potential medical value
Lucija Peterlin Mašič - One of the best experts on this subject based on the ideXlab platform.
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Rhodanine as a scaffold in drug discovery: a critical review of its biological activities and mechanisms of target modulation.
Expert opinion on drug discovery, 2012Co-Authors: Tihomir Tomašič, Lucija Peterlin MašičAbstract:Introduction: Rhodanine-based compounds have been associated with numerous biological activities. After many years of research in drug discovery, they have gained a reputation as being pan assay interference compounds (PAINS) and frequent hitters in screening campaigns. Rhodanine-based compounds are also aggregators that can non-specifically interact with target proteins as well as Michael acceptors and interfere photometrically in biological assays due to their color. Areas covered: The authors review the recently reported biological activities of Rhodanine-based compounds. Furthermore, the article provides details of their synthesis and occurrence in compound libraries through high-throughput screening (HTS) and virtual high-throughput screening (VHTS). Additionally, the authors provide the reader with possible mechanisms of non-specific target modulation, analysis of the crystal structures of enzyme–Rhodanine complexes and a comparison of Rhodanine and thiazolidine-2,4-dione moieties. Expert opinion: T...
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Rhodanine as a privileged scaffold in drug discovery.
Current medicinal chemistry, 2009Co-Authors: Tihomir Tomašič, Lucija Peterlin MašičAbstract:Rhodanines, thiazolidine-2,4-diones and pseudothiohydantoins have become a very interesting class of heterocyclic compounds since the introduction of various glitazones and epalrestat into clinical use for the treatment of type II diabetes mellitus and diabetic complications, respectively. Chemical modifications of these heterocycles constantly result in compounds with a wide spectrum of pharmacological activities. 5-ArylideneRhodanines are frequently identified as potent hits in high throughput screening against various prokaryotic and eukaryotic targets. Synthesis of substituted Rhodanines, based on high throughput screening hits, often leads to potent and selective modulators of targeted enzymes or receptors, which exert their pharmacological activities through different mechanisms of action. Due to various possibilities of chemical derivatization of the Rhodanine ring, Rhodanine-based compounds will probably remain a privileged scaffold in drug discovery. We have therefore reviewed their biological activities, mechanism of action, structure activity relationship and selectivity against other targets.
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Chapter 8:Rhodanine
Drug Discovery, 1Co-Authors: Tihomir Tomašič, Lucija Peterlin MašičAbstract:Rhodanine has been associated with a wide variety of pharmacological activities and has been the target of extensive scientific debate in the past few years. Attention has been focused on the suggested problematic behaviour of compounds containing the Rhodanine moiety, following the description by Baell et al. of Rhodanines as frequent hitters or pan assay interference compounds (PAINS). The authors suggested, therefore, that Rhodanines should be excluded from the compound libraries used for biomolecular screening and provided filters for eliminating such compounds using computational tools. Interest in Rhodanines, nevertheless, still remains, with reports of their novel biological activities that highlight the Rhodanine moiety as a privileged scaffold in the search for new biologically active compounds. This chapter describes the physicochemical properties and reactivities of Rhodanines, followed by discussion about their biological activities, particularly their antibacterial, antiviral and anticancer activities. Finally, we highlight examples of Rhodanine-based compounds progressing to clinical studies and use in therapy.
Tihomir Tomašič - One of the best experts on this subject based on the ideXlab platform.
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Rhodanine as a scaffold in drug discovery: a critical review of its biological activities and mechanisms of target modulation.
Expert opinion on drug discovery, 2012Co-Authors: Tihomir Tomašič, Lucija Peterlin MašičAbstract:Introduction: Rhodanine-based compounds have been associated with numerous biological activities. After many years of research in drug discovery, they have gained a reputation as being pan assay interference compounds (PAINS) and frequent hitters in screening campaigns. Rhodanine-based compounds are also aggregators that can non-specifically interact with target proteins as well as Michael acceptors and interfere photometrically in biological assays due to their color. Areas covered: The authors review the recently reported biological activities of Rhodanine-based compounds. Furthermore, the article provides details of their synthesis and occurrence in compound libraries through high-throughput screening (HTS) and virtual high-throughput screening (VHTS). Additionally, the authors provide the reader with possible mechanisms of non-specific target modulation, analysis of the crystal structures of enzyme–Rhodanine complexes and a comparison of Rhodanine and thiazolidine-2,4-dione moieties. Expert opinion: T...
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Rhodanine as a privileged scaffold in drug discovery.
Current medicinal chemistry, 2009Co-Authors: Tihomir Tomašič, Lucija Peterlin MašičAbstract:Rhodanines, thiazolidine-2,4-diones and pseudothiohydantoins have become a very interesting class of heterocyclic compounds since the introduction of various glitazones and epalrestat into clinical use for the treatment of type II diabetes mellitus and diabetic complications, respectively. Chemical modifications of these heterocycles constantly result in compounds with a wide spectrum of pharmacological activities. 5-ArylideneRhodanines are frequently identified as potent hits in high throughput screening against various prokaryotic and eukaryotic targets. Synthesis of substituted Rhodanines, based on high throughput screening hits, often leads to potent and selective modulators of targeted enzymes or receptors, which exert their pharmacological activities through different mechanisms of action. Due to various possibilities of chemical derivatization of the Rhodanine ring, Rhodanine-based compounds will probably remain a privileged scaffold in drug discovery. We have therefore reviewed their biological activities, mechanism of action, structure activity relationship and selectivity against other targets.
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Chapter 8:Rhodanine
Drug Discovery, 1Co-Authors: Tihomir Tomašič, Lucija Peterlin MašičAbstract:Rhodanine has been associated with a wide variety of pharmacological activities and has been the target of extensive scientific debate in the past few years. Attention has been focused on the suggested problematic behaviour of compounds containing the Rhodanine moiety, following the description by Baell et al. of Rhodanines as frequent hitters or pan assay interference compounds (PAINS). The authors suggested, therefore, that Rhodanines should be excluded from the compound libraries used for biomolecular screening and provided filters for eliminating such compounds using computational tools. Interest in Rhodanines, nevertheless, still remains, with reports of their novel biological activities that highlight the Rhodanine moiety as a privileged scaffold in the search for new biologically active compounds. This chapter describes the physicochemical properties and reactivities of Rhodanines, followed by discussion about their biological activities, particularly their antibacterial, antiviral and anticancer activities. Finally, we highlight examples of Rhodanine-based compounds progressing to clinical studies and use in therapy.
Sreekantha B. Jonnalagadda - One of the best experts on this subject based on the ideXlab platform.
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Drug screening of Rhodanine derivatives for antibacterial activity.
Expert opinion on drug discovery, 2019Co-Authors: Suresh Maddila, Sridevi Gorle, Sreekantha B. JonnalagaddaAbstract:Introduction: Bacteriological infections are a major risk to human health. These include all hospital and public-acquired infections. In drug discovery, Rhodanines are privileged heterocyclic frameworks. Their derivatives possess strong anti-bacterial activity and some of them have shown potent activity against multidrug-resistant pathogens, both under in vitro and in vivo conditions. To treat multi-drug resistant pathogens, the development of novel potent drugs, with superior anti-bacterial efficacy, is paramount. One avenue which shows promise is the design and development of novel Rhodanines.Areas covered: This review summarizes the status on Rhodanine-based derivatives and their anti-bacterial activity, based on published research over the past six years. Furthermore, to facilitate the design of novel derivatives with improved functions, their structure-activity relationships are assessed with reference to their efficacy as anti-bacterial agents and their toxicity.Expert opinion: The pharmacological activity of molecules bearing a Rhodanine scaffold needs to be very critically assessed in spite of considerable information available from various biological evaluations. Although, some data on structure-activity relationship frameworks is available, information is not adequate to optimize the efficacy of Rhodanine derivatives for different applications.
Mui Mui Sim - One of the best experts on this subject based on the ideXlab platform.
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Solid-phase combinatorial synthesis of 5-arylalkylidene Rhodanine
Tetrahedron Letters, 2000Co-Authors: Cheng Leng Lee, Mui Mui SimAbstract:Abstract Rhodanine-3-acetic acid was loaded on Wang resin or Rink amide resin. Alternatively, the thiocarbonyldiimidazole-activated Wang amino acid resin or 2-chlorotrityl resin was reacted with methyl thioglycolate to yield the Rhodanine moieties. It was then condensed at the C-5 active methylene with either aromatic aldehydes or aromatic ketones. 5-Arylalkylidene Rhodanine was obtained upon resin cleavage.