858020-17-4

Upstream product

• 75112-65-1 2-(4-nitrophenylamino)-1,4-naphthoquinone 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 6628-97-3 2-(phenylamino)naphthoquinone 
• 100-01-6 4-nitro-aniline 
• 130-15-4 [1,4]naphthoquinone 
• 71026-66-9 N-(tert-butoxycarbonyl)-1,4-phenylenediamine 
• 106-50-3 1,4-phenylenediamine 

Downstream Products

• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 363590-96-9 N-[4-(1,4-dioxo-1,4-dihydro-naphthalen-2-ylamino)-phenyl]-acetamide 

Relevant academic research and scientific papers

1,4 - Naphthoquinone derivative. Synthesis method and application

The invention relates to the technical field of drug synthesis, in particular to 1,4 - naphthoquinone derivative, a synthesis method and application thereof. The compound represented by the formula VI is synthesized from the starting materials to obtain a

Quinone-amino acid conjugates targeting leishmania amino acid transporters

The aim of the present study was to investigate the feasibility of targeting Leishmania transporters via appropriately designed chemical probes. Leishmania donovani, the parasite that causes visceral leishmaniasis, is auxotrophic for arginine and lysine and has specific transporters (LdAAP3 and LdAAP7) to import these nutrients. Probes 1-15 were originated by conjugating cytotoxic quinone fragments (II and III) with amino acids (i.e. arginine and lysine) by means of an amide linkage. The toxicity of the synthesized conjugates against Leishmania extracellular (promastigotes) and intracellular (amastigotes) forms was investigated, as well their inhibition of the relevant amino acid transporters. We observed that some conjugates indeed displayed toxicity against the parasites; in particular, 7 was identified as the most potent derivative (at concentrations of 1 μg/mL and 2.5 μg/mL residual cell viability was reduced to 15% and 48% in promastigotes and amastigotes, respectively). Notably, 6, while retaining the cytotoxic activity of quinone II, displayed no toxicity against mammalian THP1 cells. Transport assays indicated that the novel conjugates inhibited transport activity of lysine, arginine and proline transporters. Furthermore, our analyses suggested that the toxic conjugates might be translocated by the transporters into the cells. The non-toxic probes that inhibited transport competed with the natural substrates for binding to the transporters without being translocated. Thus, it is likely that 6, by exploiting amino acid transporters, can selectively deliver its toxic effects to Leishmania cells. This work provides the first evidence that amino acid transporters of the human pathogen Leishmania might be modulated by small molecules, and warrants their further investigation from drug discovery and chemical biology perspectives.

C-H functionalization of 1,4-naphthoquinone by oxidative coupling with anilines in the presence of a catalytic quantity of copper(II) acetate

The oxidative addition of anilines (2) with 1,4-naphthoquinone (3) to give N-aryl-2-amino-1,4-naphthoquinones (1) was found to be catalyzed by copper(II) acetate. In the absence of the catalyst, the reactions are slower and give lower yields with the formation of many colateral products. In the presence of 10 mol % hydrated copper(II) acetate, the reactions are generally more efficient in that they are cleaner, higher yielding, and faster.

N-Dansyl-carbazoloquinone; a chemical and electrochemical fluorescent switch

A new 'push-pull' molecule having an efficient fluorophore (dansyl) in electronic communication with an active redox quencher (phenyl-carbazoloquinone) through an NH-bridge was designed and synthesized. This all-organic molecule is suggested as a highly r