29366-46-9

Usage

InChI:InChI=1/C14H14O3/c1-2-3-6-11-12(15)9-7-4-5-8-10(9)13(16)14(11)17/h4-5,7-8,15H,2-3,6H2,1H3

Upstream product

• 858436-45-0 2-butyl-naphthalene-1,3-diol 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 122-56-5 tributyl borane 
• 252863-67-5 2-butyl-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)[1,4]naphthaquinone 
• 925-19-9 dipentanoyl peroxide 
• 52422-54-5 C₁₄H₁₂O₃ 
• 123-72-8 butyraldehyde 
• 109-65-9 1-bromo-butane 
• 252863-65-3 2-butyl-4-methoxy-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)naphthalen-1-ol 

Downstream Products

• 62830-29-9 2-Butyl-3-hydroxy-4-[(4-iodo-phenyl)-hydrazono]-4H-naphthalen-1-one 
• 62830-33-5 2-Butyl-3-hydroxy-4-[(2-iodo-4-methyl-phenyl)-hydrazono]-4H-naphthalen-1-one 
• 62830-37-9 4-{N'-[3-Butyl-2-hydroxy-4-oxo-4H-naphthalen-(1Z)-ylidene]-hydrazino}-3-iodo-benzoic acid 

Relevant academic research and scientific papers

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.

Towards targeting anticancer drugs: Ruthenium(II)-arene complexes with biologically active naphthoquinone-derived ligand systems

Anticancer active metal complexes with biologically active ligands have the potential to interact with more than one biological target, which could help to overcome acquired and/or intrinsic resistance of tumors to small molecule drugs. In this paper we present the preparation of 2-hydroxy-[1,4]-naphthoquinone-derived ligands and their coordination to a RuII(η6-p-cymene)Cl moiety. The synthesis of oxime derivatives resulted in the surprising formation of nitroso-naphthalene complexes, as confirmed by X-ray diffraction analysis. The compounds were shown to be stable in aqueous solution but reacted with glutathione and ascorbic acid rather than undergoing reduction. One-electron reduction with pulse radiolysis revealed different behavior for the naphthoquinone and nitroso-naphthalene complexes, which was also observed in in vitro anticancer assays.

Synthesis and biological evaluation of lipophilic 1,4-naphthoquinone derivatives against human cancer cell lines

To examine the effect of hydrophobicity on the anticancer activity of 1,4-naphthoquinone derivatives, a series of compounds bearing a 2-O-alkyl-, 3-C-alkyl- or 2/3-N-morpholinoalkyl group were synthesized and evaluated for their anticancer activity against five human cancer cell lines in vitro. The cytotoxicity of these derivatives was assayed against HT-29, SW480, HepG2, MCF-7 and HL-60 cells by the MTT assay. Among them, 2-hydroxy-3-farnesyl-1,4-naphthoquinone (11a) was found to be the most cytotoxic against these cell lines. Our results showed that the effectiveness of compound 11a may be attributed to its suppression of the survival of HT-29. Secondly, in the Hoechst 33258 staining test, compound 11a-treated cells exhibited nuclear condensation typical of apoptosis. Additionally, cell cycle analysis by flow cytometry indicated that compound 11a arrested HT-29 cells in the S phase. Furthermore, cell death detected by Annexin V-FITC/propidium iodide staining showed that compound 11a efficiently induced apoptosis of HT-29 in a concentration-dependent manner. Taken together, compound 11a effectively inhibits colon cancer cell proliferation and may be a potent anticancer agent.

A novel and highly regioselective Cr-mediated route to functionalised quinone boronic ester derivatives

A novel and highly regioselective route to quinone boronic ester derivatives has been developed using a Fischer carbene mediated benzannulation process.

Regioselective alkylation of substituted quinones by trialkylboranes

2-Methoxy-1,4-benzoquinone can be alkylated selectively with trialkrylboranes in position 5, giving high yields of 5-alkyl-2-methoxy-1,4- benzoquinones after oxidative work up. In the case of 2-hydroxy- 1,4naphthoquinone, the same procedure leads to 3-alkylated products. A radical chain mechanism is proposed to explain the observed selectivity.