3326-89-4

Usage

Uses

Used in Pharmaceutical Industry:
[1,3]-OXATHIOLAN-2-ONE is used as a reagent for the synthesis of oxazolidin-2-one analogues, which are important in the development of antibiotics targeting methicillin-resistant Staphylococcus aureus (MRSA) strains. Its role in this application is to facilitate the creation of new compounds that can effectively combat antibiotic-resistant bacteria, addressing a significant global health concern.
Used in Polymer Science:
[1,3]-OXATHIOLAN-2-ONE is also used as a monomer in the synthesis of biodegradable linear polymers. These polymers are designed to degrade selectively in reducing environments, making them suitable for pharmaceutical applications where controlled degradation is desired. This application takes advantage of the compound's ability to form stable polymers with specific degradation properties, contributing to the development of more sustainable and targeted drug delivery systems.

InChI:InChI=1/C3H4O2S/c4-3-5-1-2-6-3/h1-2H2

Upstream product

• 108-98-5 thiophenol 
• 1401539-53-4 C₄₀H₃₉N₃O₆PS₂⁽¹⁺⁾ 
• 65225-58-3 2-ethoxy-1,3-oxathiolane 

Downstream Products

• 505-29-3 1,4-Dithiane 
• 420-12-2 thirane 
• 25538-71-0 1-(N-benzylamino)-2-propanethiol 
• 103020-32-2 1-Cyclohexylamino-propane-2-thiol 
• 5891-06-5 2-decylamino ethanethiol 
• 5891-19-0 Benzylcarbamidsaeure-(2-mercapto-aethylester) 
• 5978-34-7 2-benzylaminoethanethiol 
• 5842-00-2 2-(butylamino)ethanethiol 
• 100-38-9 2-(diethylamine)ethanethiol 
• 5842-08-0 2-dibutylamino-ethanethiol 
• 5977-96-8 2-cyclohexylamino-ethanethiol 
• 91343-65-6 2-<2-Cyclohexylamino-aethylmercapto>-aethanthiol 
• 5978-06-3 Hexyl-carbamidsaeure-(2-mercapto-ethylester) 
• 5891-04-3 2-Hexylamino-ethylmercaptan 

Relevant academic research and scientific papers

The biothiol-triggered organotrisulfide-based self-immolative fluorogenic donors of hydrogen sulfide enable lysosomal trafficking

Biothiol-reactive organotrisulfide-based self-immolative fluorogenic donors of H2S are rationally designed for the efficient monitoring of intracellular and lysosomal trafficking of H2S with a concomitant turn-on fluorescence. The non-toxic nature of the donors with a sustained release of H2S will certainly be helpful for their biomedical applications in the future.

Mitochondrial thioredoxin-responding off-on fluorescent probe

We synthesized a new probe, Mito-Naph, to visualize mitochondrial thioredoxin (Trx) activity in cells. A fluorescence off-on change is induced by disulfide cleavage of the probe, resulting from a reaction with Trx and subsequent intramolecular cyclization by the released thiolate to give a fluorescent product. By measuring the fluorescence at 540 nm, Trx activity can be detected at nanomolar concentrations (down to 50 nM) well below its physiological levels. The in vitro and in vivo Trx preference of Mito-Naph was demonstrated by fluorometric and confocal microscopic experiments. In vitro kinetic analysis of the disulfide bond cleavage revealed that the second-order rate constant for Trx is (4.04 ± 0.26) × 103 (M s) -1, approximately 5000 times faster than that for GSH. The inhibition experiments involving PX-12, a selective inhibitor of Trx, also revealed that the emission from Mito-Naph significantly decreased in PX-12 dose-dependent manners, both in living cells and in cellular protein extracts. The Trx preference was further supported by an observation that the fluorescence intensity of rat liver extract was decreased according to the Trx depletion by immunoprecipitation. On the basis of these results, it is concluded that Mito-Naph preferentially reacts with Trx, compared with other biological thiols containing amino acids in vitro and in vivo.

HOMOLYTIC LIQUID-PHASE TRANSFORMATIONS OF 2-ETHOXY-1,3-DITHIOLANE AND 2-ETHOXY-1,3-OXATHIOLANE

The direction of the homolytic transformations in 2-ethoxy-1,3-dithiolane and 2-ethoxy-1,3-oxathiolane was investigated. 1,3-Dithiolane and 1,3-dithiolan-2-one are formed from 2-ethoxy-1,3-dithiolane, and 1,3-oxathiolane-2-one, 1,3-oxathiolane, ethyl thioformate, and diethyl monothiocarbonate are formed from 2-ethoxy-1,3-oxathiolane.The temperature dependence of the yield and ratio of the reaction products was determined.