139386-47-3Relevant 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
Ferreira, Patricia Garcia,Borba-Santos, Luana Pereira,Noronha, Leticia Lorena,Nicoletti, Caroline Deckman,De Sá Haddad Queiroz, Marcella,De Carvalho Da Silva, Fernando,Rozental, S?nia,Futuro, Débora Omena,Ferreira, Vitor Francisco
, (2019/04/02)
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.
One-Step Synthesis of Naphthofurandione, Benzofurandione, and Phenalenofuranone Derivatives by the CAN-Mediated Cycloaddition
Kobayashi, Kazuhiro,Uneda, Tomokazu,Tanaka, Koujirou,Mori, Masako,Tanaka, Hideo,Morikawa, Osamu,Konishi, Hisatoshi
, p. 1691 - 1697 (2007/10/03)
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
Kobayashi, Kazuhiro,Mori, Masako,Uneda, Tomokazu,Morikawa, Osamu,Konishi, Hisatoshi
, p. 451 - 452 (2007/10/03)
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 ...
Kobayashi, Kazuhiro,Sasaki, Akiyoshi,Takeuchi, Hiroyasu,Suginome, Hiroshi
, p. 115 - 122 (2007/10/02)
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.
