19996-02-2

Usage

Chemical family

Anthracene derivatives

Structural feature

Chlorinated derivative of anthracene with a hydroxyl group attached to the ninth carbon

Common use

Synthesis of organic compounds and pharmaceuticals

Reactivity

Unique structure and reactivity

Precursor

Production of dyes, pigments, and optical brighteners

Potential applications

Organic electronics and materials science

Electronic properties

Has electronic properties that make it useful in the field of organic electronics

Optical properties

Has optical properties that make it useful in the field of materials science

Industry applications

Wide range of potential uses and applications in various industries

InChI:InChI=1/C15H11ClO/c16-15-12-7-3-1-5-10(12)14(9-17)11-6-2-4-8-13(11)15/h1-8,17H,9H2

Upstream product

• 10527-16-9 10-chloro-9-anthraldehyde 
• 169105-89-9 isofagomine 

Downstream Products

• 10527-16-9 10-chloro-9-anthraldehyde 
• 19996-03-3 10-chloro-9-anthracenemethyl chloride 
• 25855-92-9 9-Brommethyl-10-chloranthracen 

Relevant academic research and scientific papers

Determination of protonation states of iminosugar-enzyme complexes using photoinduced electron transfer

A series of N-alkylated analogues of 1-deoxynojirimycin containing a fluorescent 10-chloro-9-anthracene group in the N-alkyl substituent were prepared. The anthracene group acted as a reporting group for protonation at the nitrogen in the iminosugar because an unprotonated amine was found to quench fluorescence by photoinduced electron transfer. The new compounds were found to inhibit β-glucosidase from Phanerochaete chrysosporium and α-glucosidase from Aspergillus Niger, with Ki values in the low micro- to nanomolar range. Fluorescence and inhibition versus pH studies of the β-glucosidase-iminosugar complexes revealed that the amino group in the inhibitor is unprotonated when bound, while one of the active site carboxylates is protonated.

Synthesis and chemistry of noeuromycin and isofagomine analogues

Several N-substituted analogues of noeuromycin ((2RS,3S,4R,5R)-2,3,4- trihydroxy-5-hydroxymethylpiperidine) and isofagomine ((3R,4R,5R)-3,4-dihydroxy- 5-hydroxy-methylpiperidine) were synthesised. The isofagomine analogues (3RS,4RS,5RS)-N-(2-phosphonoethyl)-3,4-dihydroxy-5-hydroxymethyl-piperidine, (3SR,4SR,5RS)-N-(2-phosphonoethyl)-3,4-dihydroxy-5-hydroxy-methylpiperidine, and (3R,4R,5R)-N-(10-chloro-9-anthracenemethyl)-3,4-dihydroxy-5-hydroxy- methylpiperidine were synthesised by direct alkylation of the corresponding azasugar. N-Substituted noeuromycin derivatives could not be made in this straightforward manner, but were made by modification of a synthesis intermediate. By this method (2RS,3S,4R,5R)-N-(4-methoxyphenyl)-2,3,4- trihydroxy-5-hydroxymethylpiperidine and (2RS,3S,4R,5R)-N-nonyl-2,3,4- trihydroxy-5-hydroxymethylpiperidine were synthesised. The stability of noeuromycin was studied and was found to depend on stereochemistry and pH. The L-fuco isomer ((2RS,3R,4R,5R)-2,3,4-trihydroxy-5-methylpiperidine) was observed to undergo a particularly facile Amadori rearrangement at neutral pH to the 3-ketopiperidine. A noeuromycin analogue, that could not undergo the Amadori rearrangement, was synthesised. Copyright