15451-41-9

Upstream product

• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 14666-76-3 phenyacetyl peroxide 
• 100-39-0 benzyl bromide 
• 36417-25-1 2-hydroxy-1,4-naphthoquinone silver salt 
• 620-05-3 iodomethylbenzene 
• 63534-41-8 1a-benzylnaphtho[2,3-b]oxirene-2,7(1aH,7aH)-dione 
• 71202-16-9 3,6-dibenzyl-4-hydroxy-5-phenyl-pyran-2-one 
• 71202-23-8 (3-Benzyl-2,4-dihydroxy-1-naphthyl)phenylmethanon 
• 316801-21-5 benzyl p-methylphenyl telluride 
• 70477-38-2 3,4-Dimethoxy-1-naphthol 
• 103-80-0 phenylacetyl chloride 
• 100-52-7 benzaldehyde 
• 100-44-7 benzyl chloride 
• 27699-93-0 2‐hydroxy‐1,4‐naphthoquinone 

Downstream Products

• 41695-65-2 2-benzoyl-3-hydroxy-[1,4]naphthoquinone 
• 101445-79-8 2-benzyl-1-oxo-indene-3-carboxylic acid 
• 101451-80-3 [2-(3-phenyl-propionyl)-phenyl]-glyoxylic acid 
• 858435-10-6 1,2,4-triacetoxy-3-(α-acetoxy-benzyl)-naphthalene 
• 1150-59-0 2-hydroxy-3-phenyl-1,4-naphthoquinone 
• 109648-61-5 [2-(2-hydroxy-3-phenyl-propionyl)-phenyl]-glyoxylic acid 
• 1402665-92-2 6-[(3-(benzyl)-1,4-dioxonaphthalen-2-yl)oxy]hexyltriphenylphosphonium bromide 
• 1402665-94-4 3-[(3-(benzyl)-1,4-dioxonaphthalen-2-yl)oxy]propyltriphenylphosphonium bromide 
• 1402666-21-0 2-benzyl-3-((6-bromohexyl)oxy)naphthalene-1,4-dione 
• 1402666-23-2 2-benzyl-3-((3-bromopropyl)oxy)naphthalene-1,4-dione 

Relevant academic research and scientific papers

Synthesis and Biological Screening of New Lawson Derivatives as Selective Substrate-Based Inhibitors of Cytochrome bo3 Ubiquinol Oxidase from Escherichia coli

The respiratory chain of Escherichia coli contains two different types of terminal oxidase that are differentially regulated as a response to changing environmental conditions. These oxidoreductases catalyze the reduction of molecular oxygen to water and contribute to the proton motive force. The cytochrome bo3 oxidase (cyt bo3) acts as the primary terminal oxidase under atmospheric oxygen levels, whereas the bd-type oxidase is most abundant under microaerobic conditions. In E. coli, both types of respiratory terminal oxidase (HCO and bd-type) use ubiquinol-8 as electron donor. Here, we assess the inhibitory potential of newly designed and synthesized 3-alkylated Lawson derivatives through L-proline-catalyzed three-component reductive alkylation (TCRA). The inhibitory effects of these Lawson derivatives on the terminal oxidases of E. coli (cyt bo3 and cyt bd-I) were tested potentiometrically. Four compounds were able to reduce the oxidoreductase activity of cyt bo3 by more than 50 percent without affecting the cyt bd-I activity. Moreover, two inhibitors for both cyt bo3 and cyt bd-I oxidase could be identified. Based on molecular-docking simulations, we propose binding modes of the new Lawson inhibitors. The molecular fragment benzyl enhances the inhibitory potential and selectivity for cyt bo3, whereas heterocycles reduce this effect. This work extends the library of 3-alkylated Lawson derivatives as selective inhibitors for respiratory oxidases and provides molecular probes for detailed investigations of the mechanisms of respiratory-chain enzymes of E. coli.

Organocatalytic Enantioselective Michael-Aldol[3+2] Annulation for the Synthesis of Nitro-Methanobenzo[7] annulenes

We report an enantioselective Michael-Aldol[3+2] annulation between 2-alkyl-3-hydroxynaphthalene-1,4-diones and nitroalkenes using a bifunctional thiourea catalyst, and a series of nitro-methanobenzo[7]annulenes with potential biological activities were synthesized in good yields with excellent enantio- and diastereoselectivities. A gram-scale synthesis and further transformation of the product demonstrated the synthetic value of this reaction.

RATIONALLY DESIGNED LAWSONE DERIVATIVES AS ANTIMICROBIALS AGAINST MULTIDRUG-RESISTANT STAPHYLOCOCCUS AUREUS

Naphthoquinone derivatives of Lawsone have been found to be effective against Staphylococcus aureus and methicillin-resistant Staphylococcus aureus (MRSA). Such compounds generally contain a substituent group at the 3-position of a specific naphthoquinone compound, i.e. 2-hydroxy-1,4-naphthoquinone. One of these derivatives referred to as compound 6c in the series exhibits potent antimicrobial activity that is comparable to that of the two commercial antibiotics ofloxacin and ciprofloxacin against the two strains of methicillin sensitive Staphylococcus aureus (MSSA; ATCC 29213 and ATCC 6538). In the case of two strains of MRSA (ATCC BAA-44 and ATCC BAA-1717) that have developed drug resistance to both ofloxacin and ciprofloxacin, the antimicrobial activity of 6c can almost rival that of vancomycin and daptomycin. Furthermore, 6c is also effective against vancomycin-intermediate and daptomycin non-susceptible strain of MRSA (ATCC 700699). Besides the efficacy, 6c has a much improved drug resistance profile in comparison with the conventional antibiotics.

Visible light-promoted Selectfluor-mediated quinone functionalization with unactivated Csp3-H components

A visible light-promoted metal-free cross-dehydrogenative-coupling (CDC) method for the alkylation of 1,4-naphthoquinones is reported using Selectfluor as a hydrogen atom transfer (HAT) agent. This protocol is suitable for a variety of 1,4-naphthoquinones and Csp3-H compounds and it facilitates the formation of pharmaceutically important quinone scaffolds under mild conditions. Using this methodology, the antimalarial drug, parvaquone, was synthesized in a single step.

Metal-free oxidative cross-dehydrogenative coupling of quinones with benzylic C(sp3)-H bonds

A metal-free cross-dehydrogenative coupling of quinones with toluene derivatives has been established. A series of quinones were subjected to reaction with toluene derivatives in the presence of di-tertbutyl peroxide (DTBP) for direct synthesis of benzylq

Organocatalytic Asymmetric Formal [3+2] Cycloaddition as a Versatile Platform to Access Methanobenzo[7]annulenes

Pharmaceutically and structurally important methanobenzo[7]annulenes were synthesized in very good yields with excellent enantio- and diastereoselectivities through an unprecedented organocatalytic formal [3+2] cycloaddition from readily available 2-alkyl-3-hydroxynaphthalene-1,4-diones and alkyl vinyl ketones.

Unusual, chemoselective etherification of 2-hydroxy-1,4-naphthoquinone derivatives utilizing alkoxymethyl chlorides: Scope, mechanism and application to the synthesis of biologically active natural product (±)-lantalucratin C

A novel etherification of 2-hydroxy-1,4-naphthoquinone derivatives with alkoxyalkyl chlorides and hydride bases is described. Precise study of the conditions and substrate scope suggested that the reaction occurs specifically in the molecule having a 2-hydroxy-1,4-benzoquinone skeleton. A chemoselective O-methylation reaction was achieved to afford a synthetically important intermediate, which offered easy access to a natural product possessing anti-tumor activity.

Growth inhibitory activity for cancer cell lines of lapachol and its natural and semi-synthetic derivatives

A series of 17 selected natural and semisynthetic 1,4-naphthoquinones were synthesized, and their growth inhibitory activity was evaluated in vitro. The compounds were tested on six human cancer cell lines using the MTT colorimetric assay. The data revealed that of the chemicals under study only lapachol, its acetate and 3-geranyllawsone displayed the highest activity, recording mean IC50 values ranging from 15 to 22 μM.

SMALL MOLECULE NAPHTHOQUINONE- AND PHTHALIMIDE-BASED LIPOCATIONS AS ANTI-PARASITIC AGENTS

Small molecule naphthoquinone- and phthalimide-based lipocations are provided, as well as methods for their use in treating or preventing anti-parasitic diseases, such as malaria, Chagas disease, and African Sleeping Sickness.

1,4-naphthoquinone cations as antiplasmodial agents: Hydroxy-, acyloxy-, and alkoxy-substituted analogues

Cations of hydroxy-substituted 1,4-naphthoquinones were synthesized and evaluated as antiplasmodial agents against Plasmodium falciparum. The atovaquone analogues were found to be inactive as antagonists of parasite growth, which was attributed to ionization of the acidic hydroxyl moiety. Upon modification to an alkoxy substituent, the antiplasmodial activity was restored in the sub-100 nM range. Optimal inhibitors were found to possess IC50 values of 17.4-49.5 nM against heteroresistant P. falciparum W2.