Novel and efficient protocol for the syntheses of N-1 substituted thiohydantoin and a bicyclothiohydantoin under solvent-free conditions

Kumar, Vinod; Rana, Hemlata; Sankolli, Ravish; Kaushik, M. P.

doi:10.1016/j.tetlet.2012.02.087

Cited by 11 publications

(6 citation statements)

References 60 publications

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“…This five-membered heterocyclic ring is present in a wide range of biologically active compounds. The biological activities have been shown by some of their derivatives are mainly, anticonvulsant [ 1 ], antiviral [ 2 ], antiproliferative [ 3 ], anticancer [ 4 – 9 ], antibacterial, antifungal [ 10 ], anxiolytic [ 11 ], antidiabetic activity [ 12 ] and also used as inhibitor of a fatty acid amide hydrolase [ 13 ]. Additionally, 2-thiohydantoins are used in synthetic chemistry as in skin hyperpigmentation applications [ 14 ], in the production of antimicrobial polyurethane coatings [ 15 ], in textile printing, polymerization catalysis [ 16 ] and as a reagent for development of dyes [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and evaluation of anticancer activity of novel 2-thioxoimidazolidin-4-one derivatives bearing pyrazole, triazole and benzoxazole moieties

Elhady

El‐Sayed

Al-nathali

2018

Chemistry Central Journal

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A novel series of substituted 2-thiohydantoin incorporated with benzoimidazole, pyrazole, triazole and/or benzoxazole moieties has been synthesized using (E)-3-[1-(4-bromophenyl)ethylideneamino]-2-thioxoimidazolidin-4-one 1 as the key starting material. The key material 1 also, reacted with an acetic anhydride, aromatic aldehydes, secondary amines, formaldehyde and triethyl orthoformate to give the corresponding acetyl, chalcone, Mannich bases and ethoxymethylene derivatives, respectively. The structures of the novel compounds were confirmed by spectral data and elemental analysis. The cytotoxic activity of all synthesized compounds was assessed in vitro against human hepatocellular cancer cell line (HePG-2) and breast carcinoma cell line (MCF-7). The bioassay results revealed that compound 14 has the best activity against HePG-2 cell line (IC50 = 2.33 μg/mL), while compound 5 has the best activity against MCF-7 cell line (IC50 = 3.98 μg/mL). Electronic supplementary materialThe online version of this article (10.1186/s13065-018-0418-1) contains supplementary material, which is available to authorized users.

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Section: Introductionmentioning

confidence: 99%

Design, synthesis and evaluation of anticancer activity of novel 2-thioxoimidazolidin-4-one derivatives bearing pyrazole, triazole and benzoxazole moieties

Elhady

El‐Sayed

Al-nathali

2018

Chemistry Central Journal

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“…The reaction takes place under solvent-free conditions at 60 °C to give the desired products in good to excellent yields (Scheme 6). 92 It is interesting to note that DETP, being more acidic and a better nucleophile than DBP, reacts faster with intermediates 50. A library of thiohydantoins with various substituents such as alkyl, cycloalkyl, or aryl groups was generated by this route.…”

Section: Account Synlettmentioning

confidence: 99%

Designed Synthesis of Diversely Substituted Hydantoins and Hydantoin-Based Hybrid Molecules: A Personal Account

Kumar¹

2021

Synlett

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Hydantoin and its analogs such as thiohydantoin and iminohydantoin have received substantial attention both from a chemical and biological point of view. Several compounds of this class have shown useful pharmacological activities such as anticonvulsant, antitumor, antiarrhythmic, herbicidal, and others that lead in some cases to clinical applications. Because of broad-spectrum activities, intensive research efforts have been dedicated in industry and academia to the synthesis and structural modifications of hydantoin and its derivatives. Realizing the importance of hydantoin in organic and medicinal chemistry, we also initiated a research program to successfully design and develop the new routes/methods resulting in the formation of hydantoin, thiohydantoin, and iminohydantoin substituted at different positions particularly at the N-1 position without following protection-deprotection strategy. Given the fact that the combination of two or more pharmacophoric groups may lead to hybrid molecules which result in a mixed mechanism of action on the biological target. We, therefore, further extended the developed strategy for the synthesis of new types of hydantoin-based hybrid molecules by combining hydantoin with a triazole, isoxazoline, and phosphate scaffolds as another pharmacophoric group to exploit diverse biological functions.

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“…Among this class of compounds, 5‐arylidene‐3‐aryl‐2‐thiohydantoins and their S ‐alkylated, N ‐alkylated, and N ‐glycosylated derivatives are a biologically important class of compounds in the fields of drugs, pharmaceutical intermediates, and agrochemicals [1,3]. For example, the 3‐substituted 5‐arylidene‐2‐thiohydantoin moiety is known to be a biologically active heterocyclic core in the areas of antiviral [4,5], anticonvulsant [6,7], antifungal [8,9], antibacterial [9,10], schistosomicidal [11], antidiabetic [12], anxiolytic [13], anticancer [14–21], and antiproliferative [22] activities (Figure 1). Also, compound I was designed and synthesized for detecting tau pathology in the brains of patients with Alzheimer's disease [23]; whereas compound II exihibits properties as potential inhibitors of NADPH oxidase (NOX) 1 and 4 [24] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and computational explorations of novel 2‐thiohydantoin nucleosides with cytotoxic activities

Khodair

Bakare

Awad

et al. 2022

Journal of Heterocyclic Chem

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A novel series of S-alkylated, N-alkylated, and N-glycosylated 2-thiohydantoin derivatives were synthesized via the reaction of (E)-5-(arylidene)-1-phenyl-2-thiohydantoins 5a-d with alkyl halides/glycosyl bromides under aqueous, anhydrous alkaline/glycosylation conditions, respectively. The structures of the novel compounds were confirmed by elemental analyses and spectral data. Computational studies using DFT calculations with B3LYP/6-31 + G (d,p) level were performed to study the electronic and geometric properties obtained from the stable structure of the investigated compounds. A good correlation was found between the quantum chemical parameters and experimental observations. The synthesized derivatives exhibited good binding interactions towards the cyclin-dependent kinase 2, especially (E)-5-(chlorobenzylidene)-3-(2 0 0.3 0 0.4 0 0.6 0 -tetra-O-acetyl-β-D-galactopyranosyl)-1-phenyl-2-thiohydantoin (11g), which have good key interactions such as the co-crystallized ligand. In addition, it had selective cytotoxic activities with IC 50 = 12.4 μM against lung cancer A549 cells.

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Novel and efficient protocol for the syntheses of N-1 substituted thiohydantoin and a bicyclothiohydantoin under solvent-free conditions

Cited by 11 publications

References 60 publications

Design, synthesis and evaluation of anticancer activity of novel 2-thioxoimidazolidin-4-one derivatives bearing pyrazole, triazole and benzoxazole moieties

Design, synthesis and evaluation of anticancer activity of novel 2-thioxoimidazolidin-4-one derivatives bearing pyrazole, triazole and benzoxazole moieties

Designed Synthesis of Diversely Substituted Hydantoins and Hydantoin-Based Hybrid Molecules: A Personal Account

Design, synthesis, and computational explorations of novel 2‐thiohydantoin nucleosides with cytotoxic activities

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