6487-92-9

Usage

Uses

Used in Pharmaceutical Research and Development:
2,3,4,6-tetra-O-acetyl-N-[(2-nitrophenyl)carbamothioyl]hexopyranosylamine is utilized as a research tool for the development of carbohydrate-based drugs and glycosidase inhibitors. Its capacity to mimic complex carbohydrate structures makes it instrumental in the design of drugs that target specific enzymatic carbohydrate recognition processes.
Used in the Study of Enzymatic Carbohydrate Recognition:
In the field of biochemistry, 2,3,4,6-tetra-O-acetyl-N-[(2-nitrophenyl)carbamothioyl]hexopyranosylamine serves as a valuable probe for understanding enzymatic carbohydrate recognition. Its unique structure allows researchers to investigate the mechanisms by which enzymes interact with carbohydrates, which is essential for the development of drugs that can modulate these interactions.
Used in Drug Design:
2,3,4,6-tetra-O-acetyl-N-[(2-nitrophenyl)carbamothioyl]hexopyranosylamine is applied in drug design to create molecules that can effectively target and modulate carbohydrate-protein interactions. Its chemical properties and structural features are leveraged to develop new therapeutic agents that can interfere with disease-related carbohydrate recognition events.
Used in Chemical Biology:
In the interdisciplinary field of chemical biology, 2,3,4,6-tetra-O-acetyl-N-[(2-nitrophenyl)carbamothioyl]hexopyranosylamine is employed to explore and manipulate carbohydrate-protein interactions. Its role in this area is to provide insights into the molecular basis of these interactions, which can lead to the discovery of new biological pathways and potential therapeutic targets.
Used in the Synthesis of Complex Carbohydrate Structures:
2,3,4,6-tetra-O-acetyl-N-[(2-nitrophenyl)carbamothioyl]hexopyranosylamine is also used in the synthesis of complex carbohydrate structures that are difficult to obtain through natural means. Its synthetic utility aids in the production of compounds for use in various biological and medicinal applications.

Upstream product

• 110-52-1 1,4-dibromo-butane 
• 150-19-6 O-methylresorcine 
• 51113-99-6 sodium 3-methoxyphenolate 
• 41214-27-1 4-(3-methoxy-phenoxy)-butyric acid 

Downstream Products

• 1446339-30-5 (S)-3-{1-[4-(3-methoxyphenoxy)butyl]piperidin-2-yl}pyridine oxalate 
• 142597-60-2 1-cyano-4-(m-methoxyphenoxy)butane 
• 87411-41-4 5-(m-methoxyphenoxy)pentanoic acid 

Relevant academic research and scientific papers

Synthesis of N-aryloxyalkylanabasine derivatives

N-Aryloxyalkylanabasine derivatives were prepared via the reaction of anabasine hydrochloride with various aryloxyhaloalkanes in the presence of potash in DMF. The reaction occurred with retention of the chiral center C-(2) of the piperidine group. Side products of bis(aryloxy)ethanes were characterized.

Design of PAP-1, a selective small molecule Kv1.3 blocker, for the suppression of effector memory t cells in autoimmune diseases

The lymphocyte K+ channel Kv1.3 constitutes an attractive pharmacological target for the selective suppression of terminally differentiated effector memory T (TEM) cells in T cell mediated autoimmune diseases, such as multiple sclerosis and type 1 diabetes. Unfortunately, none of the existing small molecule Kv1.3 blockers is selective, and many of them, such as correolide, 4-phenyl-4-[3-(methoxyphenyl)-3-oxo-2- azapropyl] cyclohexanone, and our own compound Psora-4 inhibit the cardiac K+ channel Kv1.5. By further exploring the structure activity relationship around Psora-4 through a combination of traditional medicinal chemistry and whole-cell patch-clamp, we identified a series of new phenoxyalkoxypsoralens that exhibit 2- to 50-fold selectivity for Kv1.3 over Kv1.5, depending on their exact substitution pattern. The most potent and "druglike" compound of this series, 5-(4-phenoxybutoxy)psoralen (PAP-1), blocks Kv1.3 in a use-dependent manner, with a Hill coefficient of 2 and an EC50 of 2 nM, by preferentially binding to the C-type inactivated state of the channel. PAP-1 is 23-fold selective over Kv1.5, 33- to 125-fold selective over other Kv1-family channels, and 500- to 7500-fold selective over Kv2.1, Kv3.1, Kv3.2, Kv4.2, HERG, calcium-activated K+ channels, Na+, Ca2+, and Cl- channels. PAP-1 does not exhibit cytotoxic or phototoxic effects, is negative in the Ames test, and affects cytochrome P450-dependent enzymes only at micromolar concentrations. PAP-1 potently inhibits the proliferation of human TEM cells and suppresses delayed type hypersensitivity, a TEM cell-mediated reaction, in rats. PAP-1 and several of its derivatives therefore constitute excellent new tools to further explore Kv1.3 as a target for immunosuppression and could potentially be developed into orally available immunomodulators. Copyright

Synthesis and stereochemical studies: Chemical and catalytic reductions of a new class of dihydropyrrole and tetrahydropyridine derivatives

Tetrahydropyridine derivatives 1g,h on catalytic (PtO2/H2) or hydride (LAH or NaBH4) reductions afford stereoselectively the corresponding cis-amines 20a,b.Catalytic reduction of the dihydropyrrole derivative 1e gives a complex material; while NaBH4 reduc