77189-69-6

Usage

Uses

Used in Pharmaceutical Industry:
5-Acetoxy-2-bromo-1,4-naphthoquinone is used as an intermediate in the synthesis of Plumbagin-d3 (P627002), a labeled version of Plumbagin (P627000). Plumbagin is a compound known for its ability to induce apoptosis in cancer cells, making it a promising candidate for the development of anticancer drugs. The use of 5-Acetoxy-2-bromo-1,4-naphthoquinone in this context is crucial for the production of effective and targeted cancer treatments.
Additionally, 5-Acetoxy-2-bromo-1,4-naphthoquinone is used as an inhibitor of NADPH oxidase 4, a key enzyme involved in the production of reactive oxygen species (ROS) in cells. By inhibiting this enzyme in a timeand dose-dependent manner, the compound can potentially be utilized in the development of therapies for conditions associated with excessive ROS production, such as neurodegenerative diseases, cardiovascular diseases, and certain types of cancer.

Upstream product

• 5196-28-1 juglone acetate 
• 87728-27-6 5-acetoxy-2,4-dibromonaphthol 
• 605-89-0 1,5-diacetoxynaphthalene 
• 87712-57-0 5-acetoxy-2,4,4-tribromonaphthalen-1-one 
• 141612-12-6 Acetic acid 6-bromo-5,8-dihydroxy-naphthalen-1-yl ester 
• 83-56-7 1,5-dihydroxynaphthalene 
• 108-24-7 acetic anhydride 
• 94807-85-9 5-hydroxynaphthalen-1-yl acetate 

Downstream Products

• 98-95-3 nitrobenzene 
• 115124-35-1 2-bromo-5-hydroxy-3-methyl-<1,4>naphthoquinone 
• 130548-10-6 (+)-rubiginone B2 
• 28882-53-3 (S)-8-hydroxy-3-methyl-3,4-dihydrotetraphene-1,7,12(2H)-trione 
• 1383471-02-0 acetic acid 3-(4-fluorophenyl)-4,9-dioxo-4,9-dihydronaphtho[2,3-d]isoxazol-5-yl ester 
• 1383471-03-1 3-(4-fluorophenyl)-5-hydroxynaphtho[2,3-d]isoxazole-4,9-dione 
• 1383471-07-5 1-benzyl-4-(5-methoxy-4,9-dioxo-4,9-dihydronaphtho[2,3-d]isoxazol-3-yl)pyridinium bromide 
• 1383471-08-6 4-(5-acetoxy-4,9-dioxo-4,9-dihydronaphtho[2,3-d]isoxazol-3-yl)-1-benzylpyridinium bromide 
• 1383471-09-7 1-benzyl-4-(5-hydroxy-4,9-dioxo-4,9-dihydronaphtho[2,3-d]isoxazol-3-yl)pyridinium bromide 
• 1262052-77-6 2-(2-(1,3-dioxan-2-yl)-6-(methoxymethoxy)-4-methylphenyl)-5-hydroxynaphthalene-1,4-dione 
• 1262052-80-1 3-hydroxy-2-(5-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-5-methylbenzaldehyde 

Relevant academic research and scientific papers

Asymmetric Total Synthesis of TAN-1085 Facilitated by Pd-Catalyzed Atroposelective C-H Olefination

Asymmetric total synthesis of TAN-1085 via Pd-catalyzed atroposelective C-H olefination is described. This synthesis features the gram-scale construction of axially chiral biaryls in an enantiopure form employing the readily available l-tert-leucine as th

Naphthoquinone derivative or a salt thereof as an active ingredient and horticultural fungicide containing (by machine translation)

[A] a naphthoquinone derivative or salt thereof, or a salt thereof as an active ingredient horticultural fungicide containing said derivative, and use thereof. [Solution] the ingredient, represented by the following formula. [In the formula, R1 And R2 Is, for example, are each independently a hydrogen atom, a halogen, amino, substituted C1 - C6 The alkylcarbonyloxy groups such as shown, however, R1 And R2 Is, not simultaneously hydrogen atoms, R3 Is, for example, C1 - C6 Alkyl, C3 - C8 Cycloalkyl, C1 - C6 Alkoxy groups, R5 R6 N - shown as, R4 Is, a hydrogen atom or a halogen atom, here, R5 And R6 The, each independently hydrogen atom or C1 - C6 The alkyl groups, R5 And R6 The, the nitrogen atom to which they are attached together, may form a hetero ring, however, R5 And R6 The, are not simultaneously hydrogen atoms. ][Drawing] no (by machine translation)

Synthesis of Barleriaquinones-I & II

Synthesis of two naturally occurring anthraquinones, Barleriaquinone-I (BQ-I) and Barleriaquinone-II (BQ-II) is achieved from commercially available naphthalene-1,5-diol. The anthraquinone core is constructed by utilizing simultaneous Heck and cross coupling reaction as the key step.

Novel heat shock protein 90 inhibitors suppress P-glycoprotein activity and overcome multidrug resistance in cancer cells

Heat Shock Protein 90 (Hsp90) chaperone interacts with a broad range of client proteins involved in cancerogenesis and cancer progression. However, Hsp90 inhibitors were unsuccessful as anticancer agents due to their high toxicity, lack of selectivity against cancer cells and extrusion by membrane transporters responsible for multidrug resistance (MDR) such as P-glycoprotein (P-gp). Recognizing the potential of new compounds to inhibit P-gp function and/or expression is essential in the search for effective anticancer drugs. Eleven Hsp90 inhibitors containing an isoxazolonaphtoquinone core were synthesized and evaluated in two MDR models comprised of sensitive and corresponding resistant cancer cells with P-gp overexpression (human non-small cell lung carcinoma and colorectal adenocarcinoma). We investigated the effect of Hsp90 inhibitors on cell growth inhibition, P-gp activity and P-gp expression. Structure-activity relationship analysis was performed in respect to cell growth and P-gp inhibition. Compounds 5, 7, and 9 directly interacted with P-gp and inhibited its ATPase activity. Their potential P-gp binding site was identified by molecular docking studies. In addition, these compounds downregulated P-gp expression in MDR colorectal carcinoma cells, showed good relative selectivity towards cancer cells, while compound 5 reversed resistance to doxorubicin and paclitaxel in concentration-dependent manner. Therefore, compounds 5, 7 and 9 could be promising candidates for treating cancers with P-gp overexpression.

Novel methodology for the synthesis of the benzo[b]phenanthridine and 6H-dibenzo[c,h]chromen-6-one skeletons. Reactions of 2-naphthylbenzylamines and 2-naphthylbenzyl alcohols

Novel syntheses of both the benzo[b]phenanthridine and the 6H-dibenzo[c,h]chromen-6-one motif are described. Reaction of (2-(3-bromo-1,4-dimethoxynaphthalen-2-yl)phenyl)methanamine with PIFA afforded benzo[b]phenanthridine-7,12-dione, while the related nonbrominated precursor, (2-(1,4,5-trimethoxynaphthalen-2-yl)phenyl)methanamine on treatment with PIFA, furnished the ortho-quinone 1-methoxybenzo[c]phenanthridine-11,12-dione. Unexpectedly, treatment of related oxygen analogs such as (2-(1,4-dimethoxynaphthalen-2-yl)phenyl)methanol with NBS under an O2atmosphere, afforded a chromenone, 12-methoxy-6H-dibenzo[c,h]chromen-6-one.

A Divergent Enantioselective Strategy for the Synthesis of Griseusins

The first enantioselective total synthesis of griseusin A, griseusin C, 4′-deacetyl-griseusin A, and two non-native counterparts in 11–14 steps is reported. This strategy highlights a key hydroxy-directed C H olefination of 1-methylene isochroman with an

Copper-mediated oxidative trifluoromethylthiolation of quinones

A novel copper-mediated oxidative trifluoromethylthiolation of quinones was developed. This protocol provided an efficient and practical approach to a series of trifluoromethylthiolated quinones.

Determining the absolute configuration of benzopyrenomycin by optical rotation, electronic circular dichroism, and population analysis of different conformations via DFT methods and experiments

In this work, we have studied the absolute configuration of benzopyrenomycin using different density functional theory (DFT) methods, such as optical rotation (OR), electronic circular dichroism (ECD), and conformation distribution analysis for three kinds of Mosher esters at different levels, e.g., B3LYP/6-31G(d), B3LYP/6-311+G(d), and B3LYP/6-311++G(2d,p) in the gas phase and in solution, respectively. Careful investigations for different chiral Mosher esters using DFT theory exhibited the application conditions for certain chiral molecules in absolute configuration determination. Benzopyrenomycin possesses a unique benzo[a]pyrene-type skeleton and shows strong cytotoxicity against various tumor-cell lines.

Total synthesis of jadomycins B, S, T, and ILEVS1080

Sweetening up jadomycin A: The first total synthesis of jadomycins B, S, T, and ILEVS1080 has been achieved, featuring construction of the unique 8H-benz[b]oxazolo[3,3-f]phenanthridine skeleton by biomimetic condensation of a quinone aldehyde with amino acid sodium salts and elaboration of the glycosides by Mitsunobu condensation (see figure). Copyright

A diastereoselective oxa-pictet-spengler-based strategy for (+)-frenolicin B and epi -(+)-frenolicin B synthesis

An efficient diastereoselective oxa-Pictet-Spengler reaction strategy was developed to construct benzoisochroman diastereomers. The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor analogs. The method is versatile and offers exquisite stereocontrol and, as such, offers a synthetic advance for the synthesis of pyranonaphthoquinone analogs.