52431-65-9

Upstream product

• 69833-10-9 3-bromo-5-methoxy-1,4-naphthoquinone 
• 77197-58-1 5-acetoxy-3-bromo-1,4-naphthoquinone 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 861357-78-0 2,3-dibromo-5-hydroxy-2,3-dihydro-[1,4]naphthoquinone 
• 83-56-7 1,5-dihydroxynaphthalene 

Downstream Products

• 15254-76-9 8-hydroxy-2-methoxynaphthalene-1,4-dione 
• 15127-94-3 2-methoxy-5-hydroxy-1,4-naphthoquinone 
• 142891-78-9 2-(3,5-Di-tert-butyl-4-hydroxyphenyl)-5-hydroxy-1,4-naphthochinon 
• 142891-79-0 3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-5-hydroxy-1,4-naphthochinon 
• 142891-76-7 3-Brom-2-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-hydroxy-1,4-naphthochinon 
• 142891-80-3 2,3-Bis-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-hydroxy-1,4-naphthochinon 
• 117-10-2 1,8-dihydroxy-9,10-anthracenedione 
• 139932-86-8 3-Acetyl-1-benzyl-8-hydroxy-2-methyl-1H-benzo[f]indole-4,9-dione 
• 139932-91-5 5-Benzyl-7-hydroxy-3-methyl-2,3,4,5-tetrahydro-benzo[b]carbazole-1,6,11-trione 
• 68749-87-1 2-Benzyl-3-bromjuglon 
• 264881-37-0 5-Benzyloxy-3-bromo-1,4-naphthoquinone 
• 481-74-3 Chrysophanol 
• 222728-58-7 5-Benzyloxy-3-bromo-1,4-dimethoxynaphthalene 
• 264881-52-9 3-Acetyl-5-benzyloxy-1,4-dimethoxynaphthalene 

Relevant academic research and scientific papers

Regiospecific synthesis of bromojuglone derivatives

A large yield highly regiospecific one step procedure for the synthesis of 2- and 3-bromo-5-acetoxy-1,4-naphthoquinone has been achieved from the reaction between N-bromosuccin-imide and 1,5- and 1,8-diacetoxynaphthalene, respectively.

Synthetic Studies of the Rubellin Natural Products: Development of a Stereoselective Strategy and Total Synthesis of (+)-Rubellin C

This manuscript describes our studies of the class of natural products known as the rubellins, culminating in the total synthesis of (+)-rubellin C. These anthraquinone-based natural products contain a variety of stereochemical and architectural motifs, including a 6-5-6-fused ring system, 5 stereogenic centers, and a central quaternary center. Herein, we report our development of a strategy to target the stereochemically dense core and anthraquinone nucleus, including approaches such as a bifunctional allylboron and vinyl triflate reagent, an anthraquinone benzylic metalation strategy, and a late-stage anthraquinone introduction strategy. Our studies culminate in a successful route to highly functionalized anthraquinone-based natural product scaffolds and a stereoselective total synthesis of (+)-rubellin C. These strategies and outcomes will aid in synthetic planning toward anthraquinone-based natural products of high interest.

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)

Lawsone, Juglone, and β-Lapachone Derivatives with Enhanced Mitochondrial-Based Toxicity

Naphthoquinones are among the most active natural products obtained from plants and microorganisms. Naphthoquinones exert their biological activities through pleiotropic mechanisms that include reactivity against cell nucleophiles, generation of reactive oxygen species (ROS), and inhibition of proteins. Here, we report a mechanistic antiproliferative study performed in the yeast Saccharomyces cerevisiae for several derivatives of three important natural naphthoquinones: lawsone, juglone, and β-lapachone. We have found that (i) the free hydroxyl group of lawsone and juglone modulates toxicity; (ii) lawsone and juglone derivatives differ in their mechanisms of action, with ROS generation being more important for the former; and (iii) a subset of derivatives possess the capability to disrupt mitochondrial function, with β-lapachones being the most potent compounds in this respect. In addition, we have cross-compared yeast results with antibacterial and antitumor activities. We discuss the relationship between the mechanistic findings, the antiproliferative activities, and the physicochemical properties of the naphthoquinones.

Total synthesis of viridicatumtoxin B and analogues thereof: Strategy evolution, structural revision, and biological evaluation

The details of the total synthesis of viridicatumtoxin B (1) are described. Initial synthetic strategies toward this intriguing tetracycline antibiotic resulted in the development of key alkylation and Lewis acid-mediated spirocyclization reactions to form the hindered EF spirojunction, as well as Michael-Dieckmann reactions to set the A and C rings. The use of an aromatic A-ring substrate, however, was found to be unsuitable for the introduction of the requisite hydroxyl groups at carbons 4a and 12a. Applying these previous tactics, we developed stepwise approaches to oxidize carbons 12a and 4a based on enol- and enolate-based oxidations, respectively, the latter of which was accomplished after systematic investigations that revealed critical reactivity patterns. The herein described synthetic strategy resulted in the total synthesis of viridicatumtoxin B (1), which, in turn, formed the basis for the revision of its originally assigned structure. The developed chemistry facilitated the synthesis of a series of viridicatumtoxin analogues, which were evaluated against Gram-positive and Gram-negative bacterial strains, including drug-resistant pathogens, revealing the first structure-activity relationships within this structural type.

NOVEL PREPARATION OF ANTICANCER-ACTIVE TRICYCLIC COMPOUNDS VIA ALKYNE COUPLING REACTION

The present invention is directed to provide a novel preparation of anticancer-active tricyclic compounds via alkyne coupling reaction. The present invention provides a process for preparing a compound of formula (Ia) or (Ib): wherein R1 is optionally substituted C1-6 alkyl, etc.; W is O, S or NR2; R2 is hydrogen atom, etc., which comprises Step (a) in which a compound of formula (II): wherein R1 is the same as defined above, and a compound of formula (III) or (IV): wherein R2 is the same as defined above; R3 is hydrogen atom, etc.; X is halogen atom, etc., are reacted in the presence of a base, a copper catalyst and a palladium catalyst in an aprotic polar solvent.

Novel strategies for the synthesis of anthrapyran antibiotics: Discovery of a new antitumor agent and total synthesis of (S)-espicufolin

Two high-yielding strategies for the synthesis of 4H-anthra[1,2-b]pyran antibiotics have been developed giving access to novel antitumor agent 24 (ED50 1.5 m) and to (S)-espicufolin (3). A key step for the assembly of the tetracyclic 4H-anthra[1,2-b]pyran-4,7,12-trione skeleton is the nucleophilic addition of an aryl lithium species onto an aldehyde which allows the introduction of either an ynone or 1,3-diketo side chain, serving as precursors for an acid-catalysed cyclisation. The Royal Society of Chemistry.

Total synthesis of the proposed structure of the anthrapyran metabolite δ-indomycinone

The first total synthesis of the proposed structure of δ-indomycinone has been accomplished. The key steps involve the Diels-Alder reaction of a bromonaphthoquinone (6) and 1-methoxy-3-methyl-1-trimethylsiloxy-1,3-butadiene (7) to access the anthraquinone

C-Glycosylation of tri-O-benzyl-2-deoxy-D-glucose: Synthesis of naphthyl-substituted 3,6-dioxabicyclo[3.2.2]nonanes

The syntheses of naphthol 7, naphthol 8, naphthol 11 and naphthol 12 are described, starting from juglone 13. C-Glycosylation of naphthol 8 with benzyl-protected glycosyl donor 10 using trimethylsilyl trifluoromethanesulfonate and silver perchlorate or boron trifluoride-diethyl ether affords rearranged product 36 in which the glycosyl donor has undergone an unusual 1,6-hydride shift. Use of the corresponding naphthol 12 as the glycosyl acceptor under the same conditions affords the expected C-glycoside 34. Use of the naphthol 7 and naphthol 11 affords predominantly rearranged products 35 and 37 respectively, albeit in much lower yield than the reactions using the corresponding bromonaphthols. The study described herein establishes that introduction of an acetyl group to C-3, as in C-glycosylnaphthoquinone 4, as required for conversion to analogues of medermycin 1 such as 3, necessitates that the C-glycosylation step be effected before regioselective introduction of the acetyl group.

Synthesis of naphthyl C-glycosides of rearranged tri-O-benzyl-2-deoxy-D- glucose

C-Glycosylation of 3-bromonaphthol 4 with benzyl-protected glycosyl donor 19 afforded rearranged bicyclic acetal 24 in which the glycosyl donor had undergone an unusual 1,6-hydride shift. Use of the regioisomeric 2- bromonaphthol 6 with the same glycosyl donor 19 afforded the expected β-C- glycoside 22. (C) 2000 Elsevier Science Ltd.