2H-naphtho<2,3-b>pyran-5,10-dione | 110271-46-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2H-naphtho<2,3-b>pyran-5,10-dione
• 英文别名: 2H-benzo[g]chromene-5,10-dione；3,4-dehydro-2,2-desmethyl-lapachone；2H-naphtho[2,3-b]pyran-5,10-dione
• CAS: 110271-46-0
• 化学式: C₁₃H₈O₃
• 分子量: 212.205
• InChiKey: NMAATQFODBZYJW-UHFFFAOYSA-N

物化性质

• 熔点：
  160-163 °C(Solv: methanol (67-56-1))
• 沸点：
  403.5±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2H-naphtho<2,3-b>pyran-5,10-dione 在 platinum on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以77%的产率得到2H-3,4-dihydronaphtho<2,3-b>pyran-5,10-dione
  参考文献：
  名称：

  抗肿瘤药。89. Psychorubrin，一种来自Psychotria rubra的新型细胞毒性萘醌，其构效关系良好。

  摘要：

  从Psychotria rubra的酒精提取物中分离出的新萘醌在KB细胞测定中表现出显着的细胞毒性（ED50 = 3.0微克/ mL）。光谱数据被用于将精神尿蛋白的结构指定为2。制备了萘醌衍生物6、8、13和14，并表现出比精神尿蛋白更好的细胞毒活性。所有这些都是潜在的迈克尔受体，其结合已扩展。然而，当此类化合物中存在亲水性羟基时，观察到体外活性降低。

  DOI：

  10.1021/jm00394a013
• 作为产物：
  描述：

  2-羟基-1,4-萘醌 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸甲胺 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 8.5h， 生成 2H-naphtho<2,3-b>pyran-5,10-dione
  参考文献：
  名称：

  Synthesis of fused chromene-1,4-naphthoquinones via ring-closing metathesis and Knoevenagel-electrocyclization under acid catalysis and microwave irradiation

  摘要：

  Two complementary methodologies involving olefin ring-closing metathesis and Knoevenagel-electrocyclization were utilized for the synthesis of alpha-xyloidones and fused chromene-1,4-naphthoquinones 5f-n and 6. The latter methodology was performed under acid catalysis or microwave irradiation allowing the synthesis of alpha-xyloidones 5f-j in moderate to good yield, which could not be obtained via the Knoevenagel-electrocyclization method. On the other hand, the lawsone bis-alkylation (C and 0) then RCM olefin enabled the preparation of simple xyloidone 5m-n and the oxepin-1,4-naphthoquinones 6. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.068

文献信息

• Synthesis and preliminary pharmacological evaluation of new (±) 1,4-naphthoquinones structurally related to lapachol
  作者：Alcides J.M da Silva、Camilla D Buarque、Flávia V Brito、Laure Aurelian、Luciana F Macedo、Linda H Malkas、Robert J Hickey、Daniele V.S Lopes、François Noël、Yugo L.B Murakami、Noelson M.V Silva、Paulo A Melo、Rodrigo R.B Caruso、Newton G Castro、Paulo R.R Costa

  DOI：10.1016/s0968-0896(02)00100-1

  日期：2002.8

  Seven new 1,4-naphthoquinones structurally related to lapachol were synthesized from lawsone and oxygenated arylmercurials. These compounds can also be seen as pterocarpan derivatives where the A-ring was substituted by the 1,4-naphthoquinone nucleus. Pharmacological screening provided evidence of significant biological activities, including effects against proliferation of the MCF-7 human breast cancer

  分别从Lawone和含氧芳基汞合成了7个与拉帕胆有关的新的1,4-萘醌。这些化合物也可以被视为翼果烷衍生物，其中A环被1,4-萘醌核取代。药理筛选提供了重要的生物学活性的证据，包括抗MCF-7人乳腺癌细胞系增殖，抗2型单纯疱疹病毒感染以及抗蛇毒诱导的肌毒性。一种衍生物取代了氟硝西epa的结合，并表现出苯二氮卓类活性，表明新的神经活性结构基序。
• COMPOUNDS OF THE PTEROCARPANQUINONE FAMILY, METHOD FOR PREPARING THE SAME, PHARMACEUTICAL COMPOSITION CONTAINING THE NEW COMPOUNDS OF THE PTEROCARPANQUINONE FAMILY, USES AND THERAPEUTIC METHOD
  申请人：Da Silva Alcides Jose Monteiro

  公开号：US20110224289A1

  公开（公告）日：2011-09-15

  This invention belongs to the chemical-pharmaceutical field. New compounds of pterocarpanquinone family presented in formula (I) according to this invention are capable to be activated by reduction generating alkylating species intracellularly. It presents selective cytotoxic effects particularly on mammalian human and nonhuman cells that divide constantly and are useful in treating diseases and dysfunctions related to the phenomenon of undesired cell proliferation. Such compounds are also effective for the treatment of diseases or dysfunctions related to high levels of TNF-α in human and nonhuman mammals.

  这项发明属于化学制药领域。根据这项发明，公开的Pterocarpanquinone家族的新化合物在公式（I）中呈现，能够通过还原激活产生细胞内烷基化物种。它对哺乳动物人类和非人类细胞表现出选择性细胞毒作用，特别对那些不断分裂的细胞，对治疗与不受欢迎的细胞增殖现象相关的疾病和功能障碍有用。这些化合物也对治疗人类和非人类哺乳动物体内TNF-α水平过高相关的疾病或功能障碍有效。
• [EN] LAPACHONE DERIVATIVES CONTAINING TWO REDOX CENTERS AND METHODS OF USE THEREOF<br/>[FR] DÉRIVÉS DE LAPACHONE CONTENANT DEUX CENTRES REDOX ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：UNIV TEXAS

  公开号：WO2017070012A1

  公开（公告）日：2017-04-27

  Provided herein are compounds containing two redox centers including a chalcogen redox center of the formula: wherein: R1, R2, X1, X2, Y1, and m are as defined herein. Also provided herein are pharmaceutical composition of the present compounds and methods of treatment using the compounds including their use in the treatment of cancer.

  本文提供了含有两个氧化还原中心的化合物，其中包括一个硫属氧化还原中心，其化学式如下：其中：R1、R2、X1、X2、Y1和m如本文所定义。本文还提供了所述化合物的药物组合物以及使用这些化合物进行治疗的方法，包括它们在癌症治疗中的应用。
• Microwave-Promoted Palladium-Catalysed Oxyarylation of Dihydronaphthalene and Chromenes by o-Iodophenols and Its Acetates
  作者：Raquel A. C. Leão、Vagner D. Pinho、Artur S. Coelho、Camilla D. Buarque、Paula F. Moraes、Diego A. Alonso、Carmen Nájera、Paulo R. R. Costa

  DOI：10.1002/ejoc.201100365

  日期：2011.6

  The oxyarylation of dihydronaphthalene (1a), two electron-rich (1b,c) and one electron-poor (2) chromenes with different o-iodophenols and their acetates 3a–h has been investigated by using either Pd(OAc)2 (10 mol-%) as precatalyst and Ag2CO3 as base in acetone as solvent or oxime palladacycle 5 as precatalyst and dicyclohexylamine as base in DMA/H2O. The reactions, which were strongly accelerated

  二氢萘 (1a)、两个富电子 (1b,c) 和一个缺电子 (2) 色烯与不同的邻碘苯酚及其乙酸酯 3a-h 的氧芳基化已经通过使用 Pd(OAc)2 (10 mol-%) 作为预催化剂和 Ag2CO3 作为碱在丙酮中作为溶剂或肟钯环 5 作为预催化剂和二环己胺作为碱在 DMA/H2O 中。当富电子色烯与被吸电子基团取代的邻碘苯酚在 Pd(OAc)2 和 Ag2CO3 存在下反应时，在微波加热下强烈加速的反应提供了最好的产率。然而，在贫电子色烯的情况下，富电子邻碘苯酚 3g 的产率最高。
• Palladium-catalyzed oxyarylation of olefins using silver carbonate as the base. Probing the mechanism by electrospray ionization mass spectrometry
  作者：Camilla D. Buarque、Vagner D. Pinho、Boniek Gontijo Vaz、Marcos N. Eberlin、Alcides J.M. da Silva、Paulo R.R. Costa

  DOI：10.1016/j.jorganchem.2010.05.014

  日期：2010.8

  (8 and 12) and electron-poor (10) olefins by ortho-iodophenols (3a–d) was studied using Ag2CO3 as the base, in acetone, and in the presence and absence of PPh3. The corresponding adducts of oxyarylation were obtained in moderate yields. The reaction mechanism was examined by electrospray ionization mass spectrometry (ESI-MS). Cationic arylpalladium intermediate (14), formed by the oxidative insertion

  以Ag 2 CO 3为碱，在丙酮中研究了邻碘苯酚（3a - d）的Pd（OAc）2催化富电子（8和12）和贫电子（10）烯烃的氧化芳基化。在有和没有PPh的情况下3。以中等收率获得了相应的氧化芳基加合物。通过电喷雾电离质谱法（ESI-MS）检查反应机理。通过将Pd（0）氧化插入3a形成的阳离子芳基钯中间体（14）和阳离子Palladacycles（15通过14与烯烃8和12的反应获得的）被ESI-MS截获并通过ESI-MS / MS进行表征。