4-hydroxy-3-(2-methylprop-1-enyl)naphthalene-1,2-dione | 15297-99-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-hydroxy-3-(2-methylprop-1-enyl)naphthalene-1,2-dione
• 英文别名: nor-lapachol；2-hydroxy-3-(2’-methyl-propenyl)-1,4-naphthoquinone；2-hydroxy-3-(2-methylprop-1-en-1-yl)naphthalene-1,4-dione；2-hydroxy-3-(2-methylprop-1-enyl)naphthalene-1,4-dione；2-Hydroxy-3-(2-methyl-prop-1-enyl)-1,4-naphthoquinone；2-hydroxy-3-(2-methyl-1-propenyl)-1,4-naphthoquinone；2-hydroxy-3-(2'-methyl-propenyl)-1,4-naphthoquinone
• CAS: 15297-99-1
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: HXRBQSOSCSKMTM-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  393.8±42.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-(2-methylprop-1-enyl)naphthalene-1,2-dione 在 10% palladium on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以95%的产率得到4-hydroxy-3-(2-methylpropyl)naphthalene-1,2-dione
  参考文献：
  名称：

  Synthesis and evaluation of quinonoid compounds against tumor cell lines

  摘要：

  Thirty two compounds were synthesized in moderate to high yields and showed activity against cancer cells HL-60 (leukemia), MDA-MB435 (melanoma), HCT-8 (colon) and SF295 (central nervous system), with IC50 below 2 mu M for some compounds. The beta-lapachone-based 1,2,3-triazoles showed the best cytoxicity profile and emerge as promising anticancer prototypes. Insights about the reactive oxygen species (ROS) mechanism of anticancer action for some compounds were obtained by addition of 1-bromoheptane that deplete reduced glutathione (GSH) content and by using N-acetylcysteine that protects cells against apoptotic cellular death, as well by analysis of thiobarbituric acid reactive substances (TBARS) formation, and oxidative DNA damage after treatment detected by the comet assay with the bacterial enzymes formamidopyrimidine DNA-glycosylase (FPG) and endonuclease III (ENDOIII). (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.006
• 作为产物：
  描述：

  黄钟花醌 生成 4-hydroxy-3-(2-methylprop-1-enyl)naphthalene-1,2-dione
  参考文献：
  名称：

  3-芳氨基和 3-烷氧基-nor-β-拉帕酮衍生物：合成和对癌细胞系的细胞毒性

  摘要：

  以中等至高产率合成了几种 3-芳基氨基和 3-烷氧基-去甲-β-拉帕酮衍生物，发现对癌细胞 SF295（中枢神经系统）、HCT8（结肠）、MDA-MB435（黑色素瘤）、和 HL60（白血病），IC 50低于 2 μM。芳氨基对硝基和 2,4-二甲氧基取代的萘醌表现出最好的细胞毒性，而邻硝基和 2,4-二甲氧基取代的萘醌比多柔比星更具选择性，并且与前体拉帕酮相似，因此很有前景。抗癌药物开发中的新先导化合物。

  DOI：

  10.1021/jm900865m

文献信息

• Synthesis and Cytotoxicity Evaluation of a Series of 3-Alkenyl-2-Hydroxy1,4-Naphthoquinones Obtained by an Efficient Knoevenagel Condensation
  作者：Cibelle David、Antonio Lins、Tania Silva、Júlia Campos、Teresinha Silva、Gardenia Militão、Celso Camara

  DOI：10.21577/0103-5053.20180146

  日期：——

  A modified and efficient Knoevenagel condensation procedure was developed to synthesize the title compounds using β-alanine and acetic acid as catalysts, showing good to excellent yields. We used lawsone with suitable aliphatic aldehydes including isobutyraldehyde, 3-methylbutyraldehyde, 2-ethylbutyraldehyde, phenylacetaldehyde, 2-phenyl-propionaldehyde, among others. These compounds were submitted

  开发了一种改进的有效的Knoevenagel缩合方法，以β-丙氨酸和乙酸为催化剂合成标题化合物，显示出良好或优异的收率。我们使用了具有适当脂族醛的Lawsone，其中脂族醛包括异丁醛，3-甲基丁醛，2-乙基丁醛，苯基乙醛，2-苯基丙醛等。这些化合物针对三种肿瘤细胞系进行了细胞毒性筛选，这些肿瘤细胞系表现出良好至优异的细胞毒性谱。
• Synthesis and Pharmacophore Modeling of Naphthoquinone Derivatives with Cytotoxic Activity in Human Promyelocytic Leukemia HL-60 Cell Line
  作者：Elisa Pérez-Sacau、Raquel G. Díaz-Peñate、Ana Estévez-Braun、Angel G. Ravelo、Jose M. García-Castellano、Leonardo Pardo、Mercedes Campillo

  DOI：10.1021/jm060849b

  日期：2007.2.1

  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

  催化剂/ HypoGen药效团建模方法和三维定量结构-活性关系（3D-QSAR）/比较分子相似性指数分析（CoMSIA）方法已成功用于解释一组测试的51种天然和合成萘醌衍生物的细胞毒活性在人早幼粒细胞白血病HL-60细胞系中。计算模型促进了对抗肿瘤特性至关重要的配体结构元素的鉴定。高活性β-环-吡喃-1,2-萘醌[0.1 microM
• Relationship between Electrochemical Parameters, Cytotoxicity Data against Cancer Cells of 3-Thio-Substituted Nor-Beta-Lapachone Derivatives. Implications for Cancer Therapy
  作者：Yen de Paiva、Thaissa Silva、André Xavier、Mariana Cardoso、Fernando da Silva、Maria Silva、Daniel Pinheiro、Claudia Pessoa、Vitor Ferreira、Marilia Goulart

  DOI：10.21577/0103-5053.20180248

  日期：——

  potential, the reductive cleavage of the C−S−C bonding; and the anodic part controlled by the oxidation of the sulfur moiety. The compounds have shown relevant cytotoxic activity, with emphasis on 3-phenyl-thio-2,2-dimethyl2,3-dihydronaphtho[1,2-b]furan-4,5-dione (compound 2), which mechanism of molecular action was shown to be related to reactive oxygen species (ROS) release. Despite the absence of a

  电化学方法在氧化还原调节剂的表征和设计中功能强大。我们在此报告在非质子介质中对11种合成的3-硫代-取代的-nor-beta-拉帕酮的电化学研究，以及对几种癌细胞系和一种正常细胞的细胞毒性活性和相应的选择性指数的测定。四个醌是新化合物。氧化还原行为代表两个独立的系统：醌部分易于还原，并且在更大的负电势下，CS键的还原裂解；阳极部分由硫部分的氧化控制。这些化合物已显示出相关的细胞毒活性，重点是3-苯基-硫基-2,2-二甲基2,3-二氢萘并[1,2-b]呋喃-4,5-二酮（化合物2），分子作用的机理被证明与活性氧（ROS）的释放有关。尽管没有线性关系，但仍存在一种趋势：大多数具有第一波还原电位值（小于-0.65 V负值）的硫代萘醌都具有活性。亲电性较低的化合物（3-（环己基硫基）-2,2-二甲基-2,3-二氢萘并[1,2-b]呋喃-4,5-二酮，环己基衍生物）对癌细胞的细胞毒性也较小。含有硫属
• Synthesis and antitumor activity of selenium-containing quinone-based triazoles possessing two redox centres, and their mechanistic insights
  作者：Eduardo H.G. da Cruz、Molly A. Silvers、Guilherme A.M. Jardim、Jarbas M. Resende、Bruno C. Cavalcanti、Igor S. Bomfim、Claudia Pessoa、Carlos A. de Simone、Giancarlo V. Botteselle、Antonio L. Braga、Divya K. Nair、Irishi N.N. Namboothiri、David A. Boothman、Eufrânio N. da Silva Júnior

  DOI：10.1016/j.ejmech.2016.06.019

  日期：2016.10

  Selenium-containing quinone-based 1,2,3-triazoles were synthesized using click chemistry, the copper catalyzed azide-alkyne 1,3-dipolar cycloaddition, and evaluated against six types of cancer cell lines: HL-60 (human promyelocytic leukemia cells), HCT-116 (human colon carcinoma cells), PC3 (human prostate cells), SF295 (human glioblastoma cells), MDA-MB-435 (melanoma cells) and OVCAR-8 (human ovarian

  使用点击化学（铜催化叠氮化物-炔烃 1,3-偶极环加成）合成含硒醌基 1,2,3-三唑，并针对六种类型的癌细胞系进行评估：HL-60（人早幼粒细胞白血病细胞） ）、HCT-116（人结肠癌细胞）、PC3（人前列腺细胞）、SF295（人胶质母细胞瘤细胞）、MDA-MB-435（黑色素瘤细胞）和OVCAR-8（人卵巢癌细胞）。一些化合物显示 IC 50值 < 0.3 μM。还使用非肿瘤细胞（例如外周血单核（PBMC）、V79 和 L929 细胞）测定了所评估的醌的细胞毒性潜力。NAD(P)H:醌氧化还原酶 1 (NQO1) 的机制作用也得到了阐明。这些化合物可以为更有效的抗癌药物开发和递送提供有前途的新先导衍生物，并且代表了报道的最活跃的拉帕酮类之一。
• Molecular mechanism of action of new 1,4-naphthoquinones tethered to 1,2,3-1H-triazoles with cytotoxic and selective effect against oral squamous cell carcinoma
  作者：Ingrid Cavalcanti Chipoline、Anna Carolina Carvalho da Fonseca、Gabriella Ribeiro Machado da Costa、Michele Pereira de Souza、Vitor Won-Held Rabelo、Lucas N. de Queiroz、Theo Luiz Ferraz de Souza、Elan Cardozo Paes de Almeida、Paula Alvarez Abreu、Bruno Pontes、Vitor Francisco Ferreira、Fernando de Carvalho da Silva、Bruno K. Robbs

  DOI：10.1016/j.bioorg.2020.103984

  日期：2020.8

  compounds with cytotoxic effect demonstrated on different cancer types. In the present study, thirty-five 1,4-naphthoquinones tethered to 1,2,3-1H-triazoles were synthesized and the antitumor activity and molecular mechanisms were evaluated in several assays including in vitro and in vivo models of OSCC and normal oral human cells. Compounds 16a, 16b and 16 g were able to induce cytotoxicity in three different

  尽管诊断和治疗取得了进步，但是口腔鳞状细胞癌（OSCC）由于其高发病率和低存活率而成为公共卫生问题。此外，最常见的OSCC化疗药物，如卡铂和顺铂，产生重要的副作用，证明开发新药的紧迫性。萘醌是一类重要的天然产物或合成化合物，对不同类型的癌症均显示出细胞毒作用。在本研究中，合成了35个与1,2,3-1 H-三唑拴在一起的1,4-萘醌，并在包括OSCC和正常人的体内和体外模型在内的多种测定中评估了其抗肿瘤活性和分子机制。口腔人类细胞。化合物16a，16b和16g能够在人OSCC的三种不同肿瘤细胞系（SCC4，SCC9和SCC25）中诱导细胞毒性，并且比经典和化学相似的对照对肿瘤细胞更具毒性和选择性（选择性指数，SI> 2） （卡铂和Lapachol）。化合物16g显示出较高的SI值。此外，化合物16A，16B和16克SCC9细胞显著减少集落形成在测试浓度。使用高浓度化合物16a，16b和16g