186394-66-1

Basic information

• Product Name: 4-[(9,10-dihydro-9,10-dioxo-1-hydroxy-8-methoxy-2-anthracenyl)hydroxymethyl]benzonitrile
• Synonyms: 4-[(9,10-dihydro-9,10-dioxo-1-hydroxy-8-methoxy-2-anthracenyl)hydroxymethyl]benzonitrile
• CAS NO: 186394-66-1
• Molecular Weight: 385.376
• Mol File: 186394-66-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-[(9,10-dihydro-9,10-dioxo-1-hydroxy-8-methoxy-2-anthracenyl)hydroxymethyl]benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(9,10-dihydro-9,10-dioxo-1-hydroxy-8-methoxy-2-anthracenyl)hydroxymethyl]benzonitrile(186394-66-1)
• EPA Substance Registry System: 4-[(9,10-dihydro-9,10-dioxo-1-hydroxy-8-methoxy-2-anthracenyl)hydroxymethyl]benzonitrile(186394-66-1)

Safety Data

• Hazardous Substances Data: 186394-66-1(Hazardous Substances Data)

Upstream product

• 5539-66-2 1-hydroxy-8-methoxyanthraquinone 
• 105-07-7 4-cyanobenzaldehyde 

Downstream Products

• 186394-59-2 4-(1,8-Dihydroxy-9-oxo-9,10-dihydro-anthracene-2-carbonyl)-benzoic acid methyl ester 
• 186394-58-1 4-[(9,10-dihydro-1,8-dihydroxy-9-oxo-2-nathracenyl)carbonyl]benzoic acid 
• 194301-06-9 4-[(9,10-dihydro-1,8-dihydroxy-9-oxo-2-anthracenyl)carbonyl]benzonitrile 
• 186394-67-2 4-[(9,10-dihydro-9,10-dioxo-1-hydroxy-8-methoxy-2-anthracenyl)carbonyl]benzonitrile 

Relevant articles and documents

Antipsoriatic anthrones with modulated redox properties. 4. Synthesis and biological activity of novel 9,10-dihydro-1,8-dihydroxy-9-oxo-2- anthracenecarboxylic and -hydroxamic acids

A novel series of carboxylic and hydroxamic acids based on 1,8- dihydroxy-9(10H)-anthracenone were synthesized from 8-hydroxy-1-methoxy- 9,10-anthracenedione as the key intermediate and evaluated both in the bovine polymorphonuclear leukocyte 5-lipoxygenase (5-LO) assay and in the HaCaT keratinocyte proliferation assay for their enzyme inhibitory and antiproliferative activity, respectively. The most potent inhibitors in both assays were the N-methylated hydroxamic acids 5d-8d with straight chain alkyl spacers. Incorporation of these structural features on the anthracenone pharmacophore resulted in increased inhibitory activity against 5-LO while the antiproliferative activity was retained. In addition, prooxidant properties as measured by deoxyribose degradation and cytotoxicity as assessed by LDH release were largely reduced as compared with the antipsoriatic anthralin. Contrary to anthralin, antioxidant properties were observed as documented by the reactivity of the novel compounds against free radicals and inhibition of lipid peroxidation in model membranes.