First preparative biocatalytic hydrolysis and S-methylation of cyclic trithiocarbonates

Kroutil, Wolfgang; Stämpfli, Andreas A; Dahinden, R.; Jörg, Mario; Müller, Urs; Pachlatko, J. Paul

doi:10.1016/s0040-4020(02)00146-1

Cited by 8 publications

(2 citation statements)

References 16 publications

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“…The data are highly suggestive of a mode of action that involves a common intermediate. In the presence of a reducing cytoplasmic environment combined with the presence of enzymes – hydrolases, carboxylesterases, and lipases 37 – it is reasonable to believe that the methyl disulfides, thioacetates, and thiocarbonates play the role of prodrugs. 38 They may be converted to their corresponding epidisulfide pharmacophores, 1a,26c which are potentially actively concentrated within the cell via a glutathione-dependent uptake mechanism.…”

Section: Anticancer Activity and Structure–activity Relationship Studiesmentioning

confidence: 99%

“…In addition to ETP-containing compounds, we found that several monomeric or dimeric derivatives possessing modications directly on the sulfur bridge serve as competent anticancer agents; IC 50 values are <10-fold less potent compared to the parents. These include thioacetate (44), dithiocarbonate (37), trithiocarbonates (18,36,64), and alkyl disuldes (45-46). The methyl disuldes would readily be converted to the thiols through reduction or nucleophilic displacement.…”

Section: Inuence Of the Nature And Degree Of Sulfurationmentioning

confidence: 99%

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Synthesis and anticancer activity of epipolythiodiketopiperazine alkaloids

et al. 2013

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The epipolythiodiketopiperazine (ETP) alkaloids are a highly complex class of natural products with potent anticancer activity. Herein, we report the application of a flexible and scalable synthesis, allowing the construction of dozens of ETP derivatives. The evaluation of these compounds against cancer cell lines in culture allows for the first expansive structure–activity relationship (SAR) to be defined for monomeric and dimeric ETP-containing natural products and their synthetic cognates. Many ETP derivatives demonstrate potent anticancer activity across a broad range of cancer cell lines, and kill cancer cellsviainduction of apoptosis. Several traits thatbode well for the translational potential of the ETP class of natural products includeconcise and efficient synthetic access, potent induction of apoptotic cell death, activity against a wide range of cancer types, and a broad tolerance for modifications at multiple sitesthat should facilitate small-molecule drug development, mechanistic studies, and evaluation in vivo.

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Section: Anticancer Activity and Structure–activity Relationship Studiesmentioning

confidence: 99%

Section: Inuence Of the Nature And Degree Of Sulfurationmentioning

confidence: 99%

Synthesis and anticancer activity of epipolythiodiketopiperazine alkaloids

et al. 2013

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Regioselective Palladium(0)‐Catalyzed Cross‐Coupling Reactions and Metal‐Halide Exchange Reactions of Tetrabromothiophene: Optimization, Scope and Limitations

et al. 2009

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Abstract:The Suzuki reaction of tetrabromothiophene with arylboronic acids provides a regioselective approach to various 5-aryl-2,3,4-tribromothiophenes, symmetrical 2,5-diaryl-3,4-dibromothiophenes, and tetraarylthiophenes. Unsymmetrical 2,5-diaryl-3,4-dibromothiophenes are prepared by Suzuki reaction of 5-aryl-2,3,4-tribromothiophenes. Tetraarylthiophenes containing two different types of aryl groups are obtained by Suzuki reactions of 2,5-diaryl-3,4-dibromothiophenes. During the optimization of the conditions of each individual reaction, the solvent, the catalyst and the temperature play an important role. In several cases, classical conditions [use of tetrakis(triphenylphosphane)palladium(0), PdA C H T U N G T R E N N U N G (PPh 3 ) 4 , as the catalyst] gave excellent yields. The yields of those transformations which failed or proceeded sluggishly could be significantly improved by application of a new biarylmonophosphine ligand developed by Buchwald and co-workers. Regioselective metal-halide exchange reactions of tetrabromothiophene provide a convenient approach to various 2,5-disubstituted 3,4-dibromothiophenes. 5-Alkyl-2-trimethylsilyl-3,4-dibromothiophenes could be prepared in one pot by sequential addition of trimethylchlorosilane and alkyl bromides. The reaction of tetrabromothiophene with methyl chloroformate and subsequent Suzuki reactions afforded 3,4-diaryl-2,5-bis(methoxycarbonyl)thiophenes.

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Eight-Membered Rings With Four or More Heteroatoms

Щербакова¹

2008

Comprehensive Heterocyclic Chemistry IV

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First preparative biocatalytic hydrolysis and S-methylation of cyclic trithiocarbonates

Cited by 8 publications

References 16 publications

Synthesis and anticancer activity of epipolythiodiketopiperazine alkaloids

Synthesis and anticancer activity of epipolythiodiketopiperazine alkaloids

Regioselective Palladium(0)‐Catalyzed Cross‐Coupling Reactions and Metal‐Halide Exchange Reactions of Tetrabromothiophene: Optimization, Scope and Limitations

Eight-Membered Rings With Four or More Heteroatoms

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