139386-48-4

Upstream product

• 100-42-5 styrene 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 139386-36-0 (+/-)-(1α,2aα,8bα)-1,2,2a,8b-tetrahydro-8b-hydroxy-1-phenylcyclobutanaphthalene-3,4-dione 

Downstream Products

• 62452-63-5 2-phenylnaphtho[2,3-b]furan-4,9-dione 

Relevant academic research and scientific papers

Synthesis, stability studies, and antifungal evaluation of substituted α- and β-2,3-dihydrofuranaphthoquinones against sporothrix brasiliensis and sporothrix schenckii

Sporotrichosis is a neglected fungal infection caused by Sporothrix spp., which have a worldwide distribution. The standard antifungal itraconazole has been recommended as a first-line therapy. However, failure cases in human and feline treatment have been reported in recent years. This study aimed to synthesize several α- and β-2,3-dihydrofuranaphthoquinones and evaluate them against Sporothrix schenckii and Sporothrix brasiliensis—the main etiological agents of sporotrichosis in Brazil. The stability of these compounds was also investigated under different storage conditions for 3 months. The samples were removed at 0, 60, and 90 days and assessed by1H-NMR, and their in vitro antifungal susceptibility was tested. Furthermore, we evaluated the superficial changes caused by the most effective and stable compounds using scanning electron microscopy and determined their effects when combined with itraconazole. Nine dihydrofuranaphthoquinones showed good antifungal activity and stability, with MIC values of 2–32 μM. Compounds 6 and 10 were the most active dihydrofuranaphthoquinones in vitro for both species; in fungi, these compounds induced yeast–hyphae conversion and alteration in the hyphae and conidia structures. Compound 10 also exhibited a synergistic activity with itraconazole against S. schenckii, with a ΣFIC index value of 0.3. Our results indicate that Compounds 6 and 10 are potential candidates for the development of new antifungal agents for the treatment of sporotrichosis.

Synthesis, anti-proliferative activity evaluation and 3D-QSAR study of naphthoquinone derivatives as potential anti-colorectal cancer agents

Colorectal cancer (CRC) is a disease with high incidence and mortality, constituting the fourth most common cause of death from cancer worldwide. Naphthoquinones are attractive compounds due to their biological and structural properties. In this work, 36 naphthoquinone derivatives were synthesized and their activity evaluated against HT-29 cells. Overall, high to moderate anti-proliferative activity was observed in most members of the series, with 15 compounds classified as active (1.73 50 2 = 0.99 and q2 = 0.625). This model allowed proposing five new compounds with two-fold higher theoretical anti-proliferative activity, which would be worthwhile to synthesize and evaluate. Further investigations will be needed to determine the mechanism involved in the effect of most active compounds which are potential candidates for new anticancer agents.

Base-Mediated Cyclization Reaction of 2-(5-Hydroxy-1-pentynyl)benzonitriles to 4-Amino-2,3-dihydronaphtho[2,3-b]furanes and Synthesis of Furanonaphthoquinones

An efficient transformation of 2-(5-hydroxy-1-pentynyl)benzonitriles 5 to furanonaphthoquinones 11 is presented. Treatment of 5 with 1.5 equiv of NaOMe in DMSO at 140 °C for 0.5 h gave 6 in good yields. Conversion of 6 to 11 was carried out by oxidation of 6 with Fremy's salt and KH2PO4 in acetone and water, followed by dehydrogenation using palladium on charcoal in diphenylether at reflux temperature.

Synthesis and pharmacophore modeling of naphthoquinone derivatives with cytotoxic activity in human promyelocytic leukemia HL-60 cell line

Catalyst/HypoGen pharmacophore modeling approach and three-dimensional quantitative structure-activity relationship (3D-QSAR)/comparative molecular similarity indices analysis (CoMSIA) methods have been successfully applied to explain the cytotoxic activity of a set of 51 natural and synthesized naphthoquinone derivatives tested in human promyelocytic leukemia HL-60 cell line. The computational models have facilitated the identification of structural elements of the ligands that are key for antitumoral properties. The four most salient features of the highly active β-cycled-pyran-1,2-naphthoquinones [0.1 μM 50 0.6 μM] are the hydrogen-bond interactions of the carbonyl groups at C-1 (HBA1) and C-2 (HBA2), the hydrogen-bond interaction of the oxygen atom of the pyran ring (HBA3), and the interaction of methyl groups (HYD) at the pyran ring with a hydrophobic area at the receptor. The moderately active 1,4-naphthoquinone derivatives accurately fulfill only three of these features. The results of our study provide a valuable tool in designing new and more potent cytotoxic analogues.

One-Step Synthesis of Naphthofurandione, Benzofurandione, and Phenalenofuranone Derivatives by the CAN-Mediated Cycloaddition

The 3+2-type cycloaddition reaction of 2-hydroxy-1,4-naphthoquinones with various alkenes or phenylacetylene was mediated by ammonium cerium(IV) nitrate (CAN) to give the corresponding naphtho[2,3-b]furan-4,9-dione and naphtho[1,2-[furan-4,5-dione derivatives. The reaction of 2-hydroxy-1,4-benzoquinones with alkenes in the presence of CAN similarly proceeded to give benzofuran-4,7-dione and benzofuran-4,5-dione derivatives. 3-Hydroxy-1H-phenalen-1-one also underwent the CAN-mediated cycloaddition with alkenes or phenylacetylene to give the corresponding 7H-phenaleno[1,2-b]furan-7-one derivatives.

Ceric ammonium nitrate mediated cycloaddition of hydroxyquinones with alkenes for the one-step construction of furoquinone derivatives

A one-step formation of furoquinones, such as naphtho[2,3-b]furan-4,9-dione, naphtho[1,2-b]furan-4,5-dione, benzofuran-4 4,7-dione, and benzofuran-4,5-dione derivatives, by the ceric ammonium nitrate mediated [3+2] type cycloaddition of 2-hydroxy-1,4-naph

Photoinduced Molecular Transformations. Part 127. A New Photoaddition of 2-Amino-1,4-naphthoquinone with Vinylarenes and the Synthesis of 2,3-Dihydronaphthofuran-4,5-diones and 2,3-Dihydronaphthofuran-4,9-diones by β-Scission of Alkoxy Radicals Generated from the ...

Irradiation of 2-amino-1,4-naphthoquinone and excess of vinylarenes such as styrene, its para-substituted derivatives, 2-vinylpyridine and 4-vinylpyridine in benzene with a Pyrex-filtered light at room temperature under nitrogen gave 1-aryl-1,2,2a,8b-tetrahydro-8b-hydroxycyclobutanaphthalene-3,4-diones as a single product in 23-63percent yields, respectively.These cyclobutanols arise from an unprecedented stereo- and regio-selective photoaddition of an excited enol form of 2-amino-1,4-naphthoquinone with the vinylarenes.Irradiation of these cyclobutanols in benzene containing excess of mercury(II) oxide and iodine with Pyrex-filtered light then gave 2-aryl-2,3-dihydronaphthofuran-4,5-diones and/or 2-aryl-2,3-dihydronaphthofuran-4,9-diones (31-73percent yields) arising from a regioselective β-scission of the alkoxyl radicals, followed by intramolecular cyclization of the resulting radical intermediates.The substitution at the para position of the 1-phenyl group was found to control the ratio of the two types of products: a methoxy group directs the formation of the 4,5-dione exclusively, while the p-cyano group directs the formation of the 4,9-dione exclusively.This considerable dependence of the products on the substituents suggests that at least some part of the formation of the dihydrofuran ring of the 4,5 and/or 4,9-diones takes place from the ionic intermediates arising owing to β-scission. 2,3-Dihydronaphthofuran-4,5-dione was found to isomerize to 2,3-dihydrofuran-4,9-dione on silica gel.

New One-Step General Synthesis of 2,3-Dihydronaphthofuran-4,9-diones by regioselective Photoaddition of 2-Hydroxy-1,4-naphthoquinones with Various Alkenes and Its Application to a Two-Step Synthesis of Maturinone

A one-step formation of 2,3-dihydronaphthofuran-4,9-diones in 41 - 83 percent by a new 2 + 3 type regioselective photoaddition of 2-hydroxy-1,4-naphthoquinones with a variety of alkenes is reported.The dihydronaphthofurandiones can readily be trans