40815-72-3

Usage

Uses

Used in Dye and Pigment Production:
2-(prop-2-en-1-yloxy)naphthalene-1,4-dione is used as a key intermediate in the synthesis of dyes and pigments, contributing to the coloration and stability of these products.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2-(prop-2-en-1-yloxy)naphthalene-1,4-dione serves as a building block for the development of new drugs, leveraging its chemical properties to create effective medicinal compounds.
Used in Organic Compound Synthesis:
2-(prop-2-en-1-yloxy)naphthalene-1,4-dione is utilized as a versatile reagent in the synthesis of various organic compounds, enhancing the range of chemical reactions and products achievable.
Used in Antimicrobial Applications:
2-(prop-2-en-1-yloxy)naphthalene-1,4-dione is employed as an antimicrobial agent, leveraging its ability to inhibit the growth of certain microorganisms, making it useful in sanitizing and preserving products.
Used in Antifungal Applications:
In antifungal applications, 2-(prop-2-en-1-yloxy)naphthalene-1,4-dione is used to combat fungal infections, providing a means to control and prevent fungal growth in various settings.
Used in Anticancer Applications:
2-(prop-2-en-1-yloxy)naphthalene-1,4-dione is used as a potential anticancer agent, with research exploring its ability to target and inhibit the growth of cancer cells.
Used in Traditional Medicine:
In traditional medicine practices, 2-(prop-2-en-1-yloxy)naphthalene-1,4-dione is used for its potential health benefits, although its use should be approached with caution due to its toxicity at high concentrations.

Upstream product

• 556-56-9 allyl iodid 
• 36417-25-1 2-hydroxy-1,4-naphthoquinone silver salt 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 107-18-6 allyl alcohol 
• 106-95-6 allyl bromide 
• 2065-37-4 2-bromo-1,4-naphthoquinone 
• 130-15-4 [1,4]naphthoquinone 
• 1010-60-2 2-chloro-1,4-naphthoquinone 
• 1785-67-7 1,2,4-triacetyloxynaphthalene 

Downstream Products

• 40815-76-7 3-allyl-2-hydroxy-1,4-naphthoquinone 
• 17112-93-5 2-methylnaphtho<1,2-b>furan-4,5-dione 

Relevant academic research and scientific papers

Synthesis and evaluation of (±)-dunnione and its ortho-quinone analogues as substrates for NAD(P)H:quinone oxidoreductase 1 (NQO1)

Natural product (±)-dunnione (2) and its ortho-quinone analogues (3-8) were synthesized and found to be substrates for NQO1. The structure-activity relationship study revealed that the biological activity was favored by the presence of methyl group at the C ring and methoxy group at the A ring. The docking studies supported the rationalization of the metabolic studies. Deeper location in the active site of NQO1, interactions with hydrophobic pocket and C-H...π interactions with the adjacent Phe178 residue contributed to the better catalytic efficiency and specificity to NQO1. Cytotoxicity studies and determination of superoxide (O2-) production in the presence and absence of the NOQ1 inhibitor dicoumarol confirmed that the ortho-quinones exerted their antitumor activity through NQO1-mediated ROS production by redox cycling.

Microwave-induced Monohydroxymethylation and Monoalkoxylation of 1,4-Naphthoquinones

1,4-Naphthoquinones and its derivatives have been hydroxymethylated and alkoxylated in the quinone ring using, respectively, formalin or an alcohol, in the presence of K2CO3 or HgO by heating or microwave irradiation.

Microwave-induced Selective Alkoxylation of 1,4-Naphthoquinones

A new efficient alkoxylation of 1,4-naphthoquinones at the active quinonoid position is reported using alkanols and an alkenol in the presence of cerium chloride and iodine under microwave irradiation.

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.

Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile

In this work, we mainly focused on discovering compounds with good selectivity for NQO1 over CPR. The NQO1-mediated two-electron reduction of compounds would kill cancer cells selectively, while CPR-mediated one-electron reduction would induce potential hepatotoxicity. Several novel quinone-directed antitumor agents were discovered as specific NQO1 substrates through structure-activity relationship studies. Among them, compound 3,7,8-trimethylnaphtho[1,2-b]furan-4,5-dione (12b) emerged as the most specific substrate of the two-electron oxidoreductase NQO1 and could hardly be reduced by CPR. It afforded the highest selectivity between NQO1/CPR (selectivity ratio = 6.37), much higher than the control β-lapachone (selectivity ratio = 1.36), indicated 12b may possess superior safety profile. The electrochemical studies provided a reasonable explanation to the good selectivity toward NQO1. Molecular docking studies supported that 12b was capable of forming additional C-H … π interactions with Trp105 and Phe178 residues compared to the control β-lap. In addition, compound 12b was shown to kill cancer cells efficiently both in vitro and in vivo model. This work gave us a promising and novel scaffold for further investigation.

Potent antitumor activity of synthetic 1,2-naphthoquinones and 1,4-naphthoquinones

Rhinacanthone (1) and two 1,2-pyranonaphthoquinones (2,3) were synthesized and found to show very potent cytotoxicity against three cancer cell lines (KB, HeLa and HepG2) with IC50 values of 0.92-9.63 μM, whereas the corresponding hydroxylated derivative 4 had reduced cytotoxicity (IC50 values of 7.61-24.13 μM). Three 1,2-furanonaphthoquinone derivatives (5-7) were also synthesized with similar cytotoxicity as 1,2-pyranonaphthoquinones. In comparison to 1,2-naphthoquinones, six 1,4-naphthoquinones derivatives fused with pyran ring (8-10) and furan ring (11-13) were synthesized and they showed less cytotoxicity or inactive to the cancer cell lines. Moreover, compound 13 had significant cytotoxicity against HeLa cell line (IC50 value of 9.25 μM) while it showed no toxic to vero cell.

Trypanocidal activity of synthetic heterocyclic derivatives of active quinones from Tabebuia sp.

Continuing a program on the chemistry and biological activity of compounds from the Brazilian flora, the lytic activity against bloodstream forms of T. cruzi of nine new heterocyclic naphthooxazole and naphthoimidazole derivatives obtained from the reaction of naphtoquinones isolated from Tabebuia sp. (Tecoma) with amino-containing reagents has been studied. Also for the first time the biological activity of allyl derivatives of lawsone, a natural quinone from Lausonia alba inactive against T. cruzi, is reported. The introduction of an allyl group in lawsone gives rise to O-allyl-lawsone and C-allyl-lawsone that showed activity against the parasite, with ID50 values of 420.7 ± 71.1 and 330.7 ± 62.4 μmol/l, respectively. The trypanocidal activity of the naphtho cyclics synthesized from the original quinones showed no concordant behavior in relation to the parent compound. Six of nine of the synthesized compounds presented lower ID50 values than crystal violet, indicating a general trend of activity among naphthalenic heterocyclics of the oxazole/imidazole type. However, their chemical structures do not endow them with the capacity of free radical generation by biological reduction as the quinoidal moiety, nor do they have chemical reducible appendage like the nitro group of nifurtimox and benzidazole, responsible for such behaviour. As a hypothesis, the pattern of their biological actions should be focused in other aspects of their chemical structures. Because of their polycyclic planar topology, these derivatives are potential candidates for experimental tests as DNA intercalating agents.

Selective alkoxylation of 1,4-quinones

1, 4-Quinones have been alkoxylated selectively at the active quinonoid position using alkanols and alkenol in the presence of (a) Raney nickel, (b) silica gel and (c) Cubronze with iodine.

Cycloadditions in Syntheses. XXVI. 1,2-Dihydrocyclobuta-naphthalene-3,8-diones: Synthesis by Photochemical Means and Their Reactions via 2,3-Dimethylene-1,4-dioxo-1,2,3,4-tetrahydronaphthalenes

2-Chloro-1,4-naphthoquinone undergoes photochemical 2+2 addition to alkenes.Elimination of hydrogen chloride from the adducts provides a facile and general synthetic method for 1,2-dihydrocyclobutanaphthalene-3,8-diones.Heating of the latter compounds affords 2,3-dimethylene-1,2,3,4-tetrahydronaphthalene-1,4-diones, which react in situ with alkenes to give the 4+2 adducts. 1-Formyl-1,2-dihydrocyclobutanaphthalene-3,8-dione obtained by the use of the above two-step procedure using acrolein dimethylacetal as the alkene in the first step affords upon heating 1H-naphthopyran-5,10-dione via electrocyclization of the corresponding dimethylene compound.If an enone is used as the alkene in the first step, the addition occurs in a 4+2 manner to give directly 4H-naphthopyran-5,10-diones.Keywords - 1,2-dihydrocyclobutanaphthalene-3,8-dione; 1H-naphthopyran-5,10-dione; 4H-naphthopyran-5,10-dione; Benzocyclobutene method; cyclobutane annelation; phtochemical synthesis; naphthopyrandione; pyran annelation;