123475-71-8

Basic information

• Product Name: 2-(2-(4-hydroxyphenyl)ethylamino)-1,4-naphthoquinone
• Synonyms: 2-(2-(4-hydroxyphenyl)ethylamino)-1,4-naphthoquinone
• CAS NO: 123475-71-8
• Molecular Weight: 293.322
• Mol File: 123475-71-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-(2-(4-hydroxyphenyl)ethylamino)-1,4-naphthoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-(4-hydroxyphenyl)ethylamino)-1,4-naphthoquinone(123475-71-8)
• EPA Substance Registry System: 2-(2-(4-hydroxyphenyl)ethylamino)-1,4-naphthoquinone(123475-71-8)

Safety Data

• Hazardous Substances Data: 123475-71-8(Hazardous Substances Data)

Upstream product

• 51-67-2 tyrosamine 
• 2348-82-5 2-methoxy-1,4-naphthoquinone 
• 130-15-4 [1,4]naphthoquinone 

Downstream Products

• 123475-73-0 2-[2-(4-Trimethylsilanyloxy-phenyl)-ethylamino]-[1,4]naphthoquinone 

Relevant articles and documents

Antioxidant, antiproliferative, and acetylcholinesterase inhibition activity of amino alcohol derivatives from 1,4-naphthoquinone

Natural and synthetic naphthoquinones have demonstrated numerous biological activities; therefore, they provide an interesting scaffold for medicinal chemists in the search for new drugs. A series of amino alcohol derivatives from 1,4-naphthoquinone with a free (2a–e) and acetylated (3a–d) hydroxyl group were synthesized, characterized, and evaluated as antioxidant agents employing 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2-2′-azino-bis-(3-ethylbenzothiazoline-6-sulfonate) (ABTS·+) assays, as acetylcholinesterase (AChE) inhibitors and antiproliferative compounds. In the DPPH assay, compound 3d showed the better result with 51.52% of antioxidant activity at 1 mg/mL, while in ABTS·+ was 2e (47.12%). The antiproliferative activity was evaluated against six different tumor cell lines, where the particular best results were for products 2a, 2c, and 2e against cervix line HeLa, with 50% growth inhibition (GI50) of 5.6, 15.0, and 17.0 μM, respectively. All synthesized compounds presented varying degrees of response, some of them with similar results compared with the positive control 5-fluorouracil. AChE inhibition of the products was not as strong as the positive control galantamine; the most potent compound was 2e with a 50% inhibitory concentration (IC50) of 0.0586 mM, followed by 2a (0.0902 mM). No inhibition in the evaluated concentrations was observed for products 2d and 3a-d. Docking of 2a and 2e was realized against AChE in order to gain insight into the interactions made between them and the enzyme residues in its catalytic gorge. In silico calculations for all synthesized products showed their drug-like properties. Alcohol derivatives, specially 2a and 2e, could be further derivatized in the search for new and improved drugs.

A biomimetic approach to the discorhabdin alkaloids: Total syntheses of discorhabdins C and E and dethiadiscorhabdin D

The characteristic spirodienone structure of the discorhabdin alkaloids is readily formed by reaction of the tyramine-substituted indoloquinonimines 26, 35, and 36 with cupric chloride, triethylamine, and oxygen. This cyclization provides a possibly biomimetic route to discorhabdins C and E (41 and 42). The unbrominated spirodienone 40 reacts with hydrogen over Pd/C to give enone 46. Bromination at the α position gives a mixture of bromoenones that undergo smooth conversion to dethiadiscorhabdin D (4) upon treatment with basic alumina.