Synthesis of New Thiohydantoin Derivatives Under Phase Transfer Catalysis

El-Regal, M. K. Abou; Abdalha, A. A.; El‐Kassaby, M. A.; Ali, Amira T.

doi:10.1080/10426500601062007

Cited by 6 publications

(8 citation statements)

References 17 publications

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“…We found that the reaction proceeded with the formation of several polar spots on TLC; the side product(s) might be generated by Salkylation, which derives some support from previous work. 20,21 If this is the case, then N(3)-alkylation could be a problematic step in the whole pathway. In addition, we believed that, in order to avoid interference of N(3)H in C(5)-functionalization, it would be more advantageous to perform the N(3)-alkylation prior to C(5)-functionalization rather than the reverse order of transformations.…”

Section: Synthesis Of 2-thiohydantoinsmentioning

confidence: 98%

Synthesis and biological evaluation of 3-substituted 5-benzylidene-1-methyl-2-thiohydantoins as potent NADPH oxidase (NOX) inhibitors

Choi

Park

Joo

et al. 2016

Bioorganic & Medicinal Chemistry

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Section: Synthesis Of 2-thiohydantoinsmentioning

confidence: 98%

Synthesis and biological evaluation of 3-substituted 5-benzylidene-1-methyl-2-thiohydantoins as potent NADPH oxidase (NOX) inhibitors

Choi

Park

Joo

et al. 2016

Bioorganic & Medicinal Chemistry

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“…The reaction was proceeded through nucleophilic displacement under PTC conditions of solid-liquid phases such as a mixture of anhydrous potassium carbonate, dioxane, and TBAB as a heterogeneous catalyst. The corresponding alkylated product 300 was obtained in a good yield [42] (Figure 107).…”

Section: Journal Of Chemistrymentioning

confidence: 99%

“…318 using dihalocompounds such as ethylene dibromide or 1,3-dibromopropane afforded the thioalkylated dimers 319a, b, respectively, via s-alkylation pathway followed by dimerization reaction [42] (Figure 112).…”

Section: S-alkylation Ptc Alkylation Of Arylidene Derivativementioning

confidence: 99%

“…In the presence of dioxane as a solvent under PTC conditions, one-pot reaction of 3-phenyl-2-thiohydantoin 91 with CS 2 and halocompounds such as ethyl bromide or benzyl chloride afforded 5-[bis(ethylsulfanyl)methylidene]-2-(ethylsulfanyl)-3-phenyl-3,5-dihydro-4H-imidazol-4-one 328a and 5-[bis(benzylsulfanyl)methylidene]-2-(benzylsulfanyl)-3-phenyl-3,5-dihydro-4H-imidazol-4-one 328b, respectively [42] (Figure 116).…”

Section: C-alkylationmentioning

confidence: 99%

“…Acylation of imidazolones 318 using chloroacetyl chloride under PTC conditions yielded the corresponding acylated arylidene derivative 329 [42] (Figure 117). 5.1.5.…”

Section: C-alkylationmentioning

confidence: 99%

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Synthesis and Reactions of Five-Membered Heterocycles Using Phase Transfer Catalyst (PTC) Techniques

El-Sayed

Allah

El‐Saghier

et al. 2014

Journal of Chemistry

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Phase transfer catalysts (PTCs) have been widely used for the synthesis of organic compounds particularly in both liquid-liquid and solid-liquid heterogeneous reaction mixtures. They are known to accelerate reaction rates by facilitating formation of interphase transfer of species and making reactions between reagents in two immiscible phases possible. Application of PTC instead of traditional technologies for industrial processes of organic synthesis provides substantial benefits for the environment. On the basis of numerous reports it is evident that phase-transfer catalysis is the most efficient way for generation and reactions of many active intermediates. In this review we report various uses of PTC in syntheses and reactions of five-membered heterocycles compounds and their multifused rings.

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5-Arylidenethioxothiazolidinones as Inhibitors of Tyrosyl–DNA Phosphodiesterase I

et al. 2012

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Tyrosyl-DNA phosphodiesterase I (Tdp1) is a cellular enzyme that repairs the irreversible topoisomerase I (Top1)-DNA complexes and confers chemotherapeutic resistance to Top1 inhibitors. Inhibiting Tdp1 provides an attractive approach to potentiating clinically used Top1 inhibitors. However, despite recent efforts in studying Tdp1 as a therapeutic target, its inhibition remains poorly understood and largely underexplored. We describe herein the discovery of arylidene thioxothiazolidinone as a scaffold for potent Tdp1 inhibitors based on an initial tyrphostin lead compound 8. Through structure-activity relationship (SAR) studies we demonstrated that arylidene thioxothiazolidinones inhibit Tdp1 and identified compound 50 as a submicromolar inhibitor of Tdp1 (IC₅₀ = 0.87 μM). Molecular modeling provided insight into key interactions essential for observed activities. Some derivatives were also active against endogenous Tdp1 in whole cell extracts. These findings contribute to advancing the understanding on Tdp1 inhibition.

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Synthesis of New Thiohydantoin Derivatives Under Phase Transfer Catalysis

Cited by 6 publications

References 17 publications

Synthesis and biological evaluation of 3-substituted 5-benzylidene-1-methyl-2-thiohydantoins as potent NADPH oxidase (NOX) inhibitors

Synthesis and biological evaluation of 3-substituted 5-benzylidene-1-methyl-2-thiohydantoins as potent NADPH oxidase (NOX) inhibitors

Synthesis and Reactions of Five-Membered Heterocycles Using Phase Transfer Catalyst (PTC) Techniques

5-Arylidenethioxothiazolidinones as Inhibitors of Tyrosyl–DNA Phosphodiesterase I

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