CAS: 483-55-6; 2-Hydroxy-3-Methylnaphthalene-1,4-Dione

该化合物是一种具有显著化学特性的环烷基酮衍生物,包括它作为有机合成中多用途中间体的作用,其结构上有一个氢氧基组和一个五角星核心的甲基替代体,加强了其在红氧化工艺和电益替代中的回活动.该化合物由于其作为生物活性分子前体的潜力,在制药和农用化学研究中特别宝贵.在受控条件下的稳定性和与各种反应条件的兼容性使其适合用于热循环化学和材料科学的应用.该化合物定义明确的晶体形式确保实验室环境的纯度和处理.

结构式图片

欧盟法规

REACH注册ECHA物质C&L通报REACH预注册

上下游产品

3-Ethyl-4-Hydroxynaphthalene-1,2-Dione 29366-44-7
2-Methyl-3-Hydroxy-Naphthochinon-(1,4)-Acetat 09/04/6091
2-羟基-1,4-萘醌 Lawsone 83-72-7
甲萘醌 Menadione 58-27-5
乙酸1,4-二氧代-1,4-二氢萘-2-基酯 2-Acetoxy-1,4-Naphthoquinone 1785-65-5
2-氯-3-甲基萘-1,4-二酮 2-Methyl-3-Chloronaphthoquinone 17015-99-5
2-溴-3-甲基萘-1,4-二酮 2-Bromo-3-Methyl-[1,4]Naphthoquinone 3129-39-3
2-Amino-3-Methyl-1,4-Naphthoquinone 7427-09-0
2-甲基-3-(甲基氨基)-1,4-萘醌 2-Methylamino-3-Methyl-1,4-Naphthoquinone 1694-01-5
1,4-萘醌 [1,4]Naphthoquinone 130-15-4

合成工艺路线路线简述

    📜甲萘醌置于硫酸,双氧水,Sodium Carbonate体系中,用 甲醇,水 作为反应溶剂,化学反应 0.17H,反应生成 2-羟基-3-甲基-1,4-萘醌
    参考文献:通过 Rh 催化的 Ch 键活化和点击反应合成具有潜在抗肿瘤活性的硒-醌杂化化合物
    标题:通过 Rh 催化的 Ch 键活化和点击反应合成具有潜在抗肿瘤活性的硒-醌杂化化合物
    摘要:为了继续探索新的氧化还原调节催化抗肿瘤分子,使用铑催化的 Ch 键活化和点击反应合成了含硒醌基 1,2,3-三唑.所有化合物都针对五种类型的癌细胞系进行了评估:Hl-60(人早幼粒细胞白血病细胞),Hct-116(人结肠癌细胞),Sf295(人胶质母细胞瘤细胞),Ncih-460(人肺细胞)和 Pc3(人前列腺癌细胞).一些化合物显示出非常好的活性,Ic50 值低于 1 µm.萘醌衍生物的细胞毒性潜力也在非肿瘤细胞中进行了评估,例如 L929 细胞.总体而言,这些化合物代表了有前途的新先导衍生物,代表了一类具有潜在抗肿瘤活性的新型含硫衍生物.
    DOI:10.3390/molecules23010083

    海关参考信息

    专利信息


    专利号:US-8987503-B2
    优先权日:2013-04-30
    标 题 :Process for the synthesis of aminaphtone
    发明人:BALDACCI MASSIMO; ROBERTI MARINELLA
    权利人:BALDACCI LAB SPA
    摘要:The present invention concerns a new process for the synthesis of aminaphtone, which makes use of non-toxic solvents and reagents, under mild reaction and temperature conditions. The aminaphtone obtained with the method of the present invention also has a purity of at least 98% in weight. The method comprises the following steps: a) epoxidating menadione 1 to provide epoxide 2, b) acidifying epoxide 2 to provide hydroxynaphthoquinone 3, c) esterifying between hydroxynaphthoquinone 3 and 4-aminobenzoyl chloride to obtain compound 4, and d) reducing compound 4 in the presence of a reducing agent in water to obtain aminaphtone.

    专利号:US-9409879-B2
    优先权日:2011-03-29
    标 题 :Total synthesis of redox-active 1.4-naphthoquinones and their metabolites and their therapeutic use as antimalarial and schistomicidal agents
    发明人:DAVIOUD-CHARVET ELISABETH; LANFRANCHI DON ANTOINE; JOHANN LAURE; WILLIAMS DAVID LEE; CESAR RODO ELENA
    权利人:DAVIOUD-CHARVET ELISABETH; LANFRANCHI DON ANTOINE; JOHANN LAURE; WILLIAMS DAVID LEE; CESAR RODO ELENA; CENTRE NAT RECH SCIENT
    摘要:Naphthoquinones, azanaphthoquinones and benxanthones, their process of synthesis and methods of their use as antimalarial or antischistosomal agents.

    专利号:US-4459227-A
    优先权日:1981-03-02
    标 题:Para-hydroxyphenylhydrazines as in situ precursors of iminoquinones and quinones
    发明人:SAHMEL REINHARDT O; GRAHAM DOYLE G
    权利人:UNIV DUKE
    摘要:Iminoquinone precursors having the formula wherein R1 represents hydrogen or an enzymatically hydrolyzable group; R2 and R3 independently represent hydrogen, a non-electron-withdrawing organic substituent or an enzymatically hydrolyzable group except that when R1 is hydrogen, R2 must be an enzymatically hydrolyzable group and R3 must not inhibit the hydrolysis of R2; R4 represents hydrogen or an electron-withdrawing or non-electron-withdrawing organic substituent, except that if R1 is hydrogen, R4 may not inhibit the hydrolysis of R2; W, X, Y and Z independently represent hydrogen or an electron-withdrawing or non-electron-withdrawing organic substituent, or any one of X and W, Y and Z, or X and R4 taken together represents a cyclic or heterocyclic ring having 5 to 6 ring atoms; and wherein said enzymatically hydrolyzable group is selected so that a hydrolysis product is biologically benign for the biological system in which said precursor is present is produced by hydrolysis of the hydrolyzable group. Also disclosed are methods of synthesis and methods of use of these compounds.

    专利号:SU-1763444-A1
    优先权日:1990-05-08
    标题 :Method for synthesis of sulfur-containing polymer

    专利号:US-2014121238-A1
    优先权日:2011-03-29
    标 题:Total synthesis of redox-active 1.4-naphthoquinones and their metabolites and their therapeutic use as antimalarial and schistomicidal agents

    专利号:US-2014323747-A1
    优先权日:2013-04-30
    标 题:Process for the synthesis of aminaphtone

    供应商参考报价(招募中)

    品牌试剂参考报价(招募中)

    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    主要参考文献


    1: Moura-Alves P, Faé K, Houthuys E, Dorhoi A, Kreuchwig A, Furkert J, Barison N, Diehl A, Munder A, Constant P, Skrahina T, Guhlich-Bornhof U, Klemm M, Koehler AB, Bandermann S, Goosmann C, Mollenkopf HJ, Hurwitz R, Brinkmann V, Fillatreau S, Daffe M, Tümmler B, Kolbe M, Oschkinat H, Krause G, Kaufmann SH. AhR sensing of bacterial pigments regulates antibacterial defence. Nature. 2014 Aug 28;512(7515):387-92. doi: 10.1038/nature13684. Epub 2014 Aug 13. Epub 2014 Aug 5.
    3: Gardner PR. Superoxide production by the mycobacterial and pseudomonad quinoid pigments phthiocol and pyocyanine in human lung cells. Arch Biochem Biophys. 1996 Sep 1;333(1):267-74.
    8: QUAGLIARIELLO E, AURICCHIO S, SORDINO R, PIAZZA M. [Effects of phthiocol and menadione on the reaction of 3-hydroxyanthranilic acid to quinolinic acid; probable mechanism of action of their inhibiting effect]. Boll Soc Ital Biol Sper. 1957 Jan-Feb;33(1-2):159-62. Italian. Undetermined Language.

    合成参考文献


    参考文献:10.1007/bf02160833
    摘要:Pearse AGE, Hess R. Substantivity and other factors responsible for formazan patterns in dehydrogenase histochemistry. Cellular and Molecular Life Sciences. 1961 Mar;17(3):136–41. doi: 10.1007/bf02160833.
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