Selective synthesis of isomeric dithioglycerols

Леванова, Е. П.; Grabel’nykh, V. A.; Sukhomazova, E. N.; Zemirova, I. A.; Russavskaya, N. V.; Albanov, A. I.; Клыба, Л. В.; Zhanchipova, E. R.; Корчевин, Н. А.

doi:10.1134/s1070428008100059

Cited by 5 publications

(1 citation statement)

References 8 publications

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“…1,3-Dimercapto-2-propanol was prepared through a reductive cleavage of a S-S bonded polymeric mixture which was preformed from 1,3-dichloro-2-propanol and disodium disulfide. 16 The oxidation of alcohol 3 was carried out with oxalyl chloride, DMSO, and TEA at −78°C. 17 The ketone 4 was isolated in a 68% yield and IR spectrum indicated the formation of a carbonyl group with strong absorption.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of High Refractive Spiroheterocyclic Derivatives Through Thioacetalization of Multi-Carbonyl Compounds

Ye¹,

Maheswara

Yun

2012

Bulletin of the Korean Chemical Society

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Preparation of several new spirocyclic mercapto derivatives is described. Thiol protection on multi-carbonyl compounds allows of high sulfur content necessary to induce high refractive index. Condensation of 1,3-dimercapto-2-propanol and cyclohexanone followed by successive oxidation and thioacetalization affords a dispirocycle with four sulfurs. Selective S,S-protection of cyclohexane-1,4-dione is achieved with 1,3-dimercapto-2-propanol and 2,3-dimercapto-1-propanol to provide dispirocycles with four sulfurs. Olefineoxidation of norbornene gives a useful dialdehyde intermediate which is transformed to 1,3-dithiolane for a linearly-bound-cyclic molecule. Refractive index of linearly-bound-cycles was below 1.60 and dispirocycles exhibited high refractive index of 1.57-1.69.

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Section: Resultsmentioning

confidence: 99%

Synthesis of High Refractive Spiroheterocyclic Derivatives Through Thioacetalization of Multi-Carbonyl Compounds

Ye¹,

Maheswara

Yun

2012

Bulletin of the Korean Chemical Society

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Molecular Rods Based on Oligo-spiro-thioketals

et al. 2016

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We report on an extension of the previously established concept of oligospiroketal (OSK) rods by replacing a part or all ketal moieties by thioketals leading to oligospirothioketal (OSTK) rods. In this way, some crucial problems arising from the reversible formation of ketals are circumvented. Furthermore, the stability of the rods toward hydrolysis is considerably improved. To successfully implement this concept, we first developed a number of new oligothiol building blocks and improved the synthetic accessibility of known oligothiols, respectively. Another advantage of thioacetals is that terephthalaldehyde (TAA) sleeves, which are too flexible in the case of acetals can be used in OSTK rods. The viability of the OSTK approach was demonstrated by the successful preparation of some OSTK rods with a length of some nanometers.

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Highly Selective Off–On Fluorescent Probe for Imaging Thioredoxin Reductase in Living Cells

et al. 2013

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The first fluorescent probe for mammalian thioredoxin reductase (TrxR), TRFS-green, was designed, synthesized, and fully evaluated. The probe features a 1,2-dithiolane scaffold with a quenched naphthalimide fluorophore. TRFS-green displays a green fluorescence off-on change induced by the TrxR-mediated disulfide cleavage and subsequent intramolecular cyclization to liberate the masked naphthalimide fluorophore. It was demonstrated in vitro that TRFS-green manifests high selectivity toward TrxR over other related enzymes and various small molecule thiols as well as biological reducing molecules. HPLC analyses indicated that TRFS-green was exclusively converted to naphthalimide catalyzed by TrxR. The ability in triggering on the fluorescence signal by cellular protein extracts correlates well with the endogenous TrxR activity in different cells. Furthermore, inhibition of TrxR by 2,4-dinitrochlorobenzene or depletion of TrxR by immunoprecipitation remarkably decreases the reduction of TRFS-green by cellular protein extracts. Finally, TRFS-green was successfully applied in imaging TrxR activity in living cells. The fluorescence signal of TRFS-green in living cells was inhibited by pretreating the cells with TrxR inhibitor in a dose-dependent manner, potentiating the development of living cell-based screening assay for identifying TrxR inhibitors. We expect the novel fluorescent probe TRFS-green would facilitate the discovery of TrxR-targeting small molecules for potential therapeutic agents and provide significant advances in understanding the physiological/pathophysiological functions of TrxR in vivo.

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Selective synthesis of isomeric dithioglycerols

Cited by 5 publications

References 8 publications

Synthesis of High Refractive Spiroheterocyclic Derivatives Through Thioacetalization of Multi-Carbonyl Compounds

Synthesis of High Refractive Spiroheterocyclic Derivatives Through Thioacetalization of Multi-Carbonyl Compounds

Molecular Rods Based on Oligo-spiro-thioketals

Highly Selective Off–On Fluorescent Probe for Imaging Thioredoxin Reductase in Living Cells

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