1,4-dimethoxy-2-hydroxymethylnaphthalene | 150556-57-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-dimethoxy-2-hydroxymethylnaphthalene
• 英文别名: (1,4-dimethoxynaphthalen-2-yl)methanol；(1,4-Dimethoxynaphthalen-3-yl)methanol
• CAS: 150556-57-3
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: TVXWHCOBSAZDNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-dimethoxy-2-hydroxymethylnaphthalene 在 氢溴酸 、 溴 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 2-bromo-3-(bromomethyl)-1,4-dimethoxynaphthalene
  参考文献：
  名称：

  Design and Synthesis of Novel Quinone Inhibitors Targeted to the Redox Function of Apurinic/Apyrimidinic Endonuclease 1/Redox Enhancing Factor-1 (Ape1/Ref-1)

  摘要：

  The multifunctional enzyme apurinic endonuclease 1/redox enhancing factor 1 (Apel/ref-1) maintains genetic fidelity through the repair of apurinic sites and regulates transcription through redox-dependent activation of transcription factors. Apel can therefore serve as a therapeutic target in either a DNA repair or transcriptional context. Inhibitors of the redox function can be used as either therapeutics or novel tools for separating the two functions for in vitro study. Presently there exist only a few compounds that have been reported to inhibit Apel redox activity; here we describe a series of quinones that exhibit micromolar inhibition of the redox function of Apel. Benzoquinone and naphthoquinone analogues of the Apel-inhibitor E3330 were designed and synthesized to explore structural effects on redox function and inhibition of cell growth. Most of the naphthoquinones were low micromolar inhibitors of Apel redox activity, and the most potent analogues inhibited tumor cell growth with IC50 values in the 10-20 mu M range.

  DOI：

  10.1021/jm9014857
• 作为产物：
  描述：

  1,4-二羟基萘 在 sodium hydroxide 、 sodium tetrahydroborate 、 水 、 potassium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 26.5h， 生成 1,4-dimethoxy-2-hydroxymethylnaphthalene
  参考文献：
  名称：

  Synthesis of Quinones from Hydroquinone Dimethyl Ethers. Oxidative Demethylation with Cobalt(III) Fluoride

  摘要：

  用三氟化钴对1,4-二甲氧基萘和1,4-二甲氧基苯衍生物进行氧化脱甲基反应，能够获得良好至极佳的产率，从而得到相应的萘醌和苯醌衍生物。

  DOI：

  10.1055/s-1999-2875

文献信息

• Preparations of Anthraquinone and Naphthoquinone Derivatives and Their Cytotoxic Effects
  作者：Xing-Ri Cui、Ryota Saito、Takatsugu Kubo、Daijiro Kon、Yuich Hirano、Setsuo Saito

  DOI：10.1248/cpb.59.302

  日期：——

  Chrysophanol and 1,8-di-O-hexylchrysophanol derivatives having nucleic acid bases at position 5 were synthesized. Furthermore, derivatives of menadione substituted at position 11 (type A naphthoquinone derivatives) or methylmenadione substituted at position 7 (type B naphthoquinone derivatives) modified with nucleic acid bases, amines and thiocyano, selenocyano or thioacetyl groups were synthesized. The cytotoxic effects of these derivatives on HCT 116 cells, which poorly express P-glycoprotein (P-gp), and Hep G2 cells, which stably express P-gp, were evaluated by performing 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Results were compared with those obtained using 5-fluorouracil (5-FU), which has been used clinically. Several of these derivatives exhibited markedly higher potent cytotoxic effects not only on HCT cancer cells but also Hep G2 cancer cells as compared with 5-FU.

  芪二酚及在第5位具有核酸碱基的1,8-二-O-己基芪二酚衍生物被合成。此外，在第11位取代的甲萘醌（A型萘醌衍生物）或第7位取代的甲基甲萘醌（B型萘醌衍生物）与核酸碱基、胺以及硫氰酸、硒氰酸或硫代乙酰基团修饰的衍生物也被合成。通过执行3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑啉溴（MTT）实验，评估了这些衍生物对P-糖蛋白（P-gp）表达较弱的HCT 116细胞以及稳定表达P-gp的Hep G2细胞的细胞毒性效应。结果与临床使用的5-氟尿嘧啶（5-FU）获得的结果进行了比较。几种衍生物不仅对HCT癌细胞，而且对Hep G2癌细胞的细胞毒性效应都明显高于5-FU。
• Pyrimidine, quinazoline, pteridine and triazine derivatives
  申请人：Binggeli Alfred

  公开号：US20070225271A1

  公开（公告）日：2007-09-27

  This invention is concerned with compounds of the formula wherein A, R 1 to R 5 and G are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are associated with the modulation of SST receptors subtype 5.

  这项发明涉及以下式的化合物 其中A，R1至R5和G如描述和声明中所定义，并其药学上可接受的盐。该发明还涉及含有这种化合物的药物组合物，以及用于制备它们的方法和它们用于治疗和/或预防与调节SST受体亚型5相关的疾病的用途。
• Benzothiazole, thiazolopyridine, benzooxazole and oxazolopyridine derivatives
  申请人：Binggeli Alfred

  公开号：US20060205718A1

  公开（公告）日：2006-09-14

  This invention is concerned with compounds of the formula wherein A, B 1 , B 2 , R 1 , R 2 and G are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are associated with the modulation of SST receptors subtype 5.

  这项发明涉及以下式的化合物 其中A、B 1 、B 2 、R 1 、R 2 和G如描述和索赔中所定义，并其药学上可接受的盐。该发明还涉及含有这种化合物的药物组合物，以及用于制备它们的方法和它们用于治疗和/或预防与调节SST受体亚型5相关的疾病的用途。
• Domino Michael/Michael Reaction for the Formation of Chiral Spirocycles Using a Diphenylprolinol Silyl Ether
  作者：Yujiro Hayashi、Kaito Nagai、Shigenobu Umemiya

  DOI：10.1002/ejoc.201801202

  日期：2019.1.31

  construction of spiro[cyclopentane‐1,2′(1′H)‐naphthalene] derivatives through domino Michael/Michael reaction of 2‐(2‐formylethyl)naphthalene‐1,4‐dione and nitroalkenes catalysed diphenylprolinol silyl ether.

  新的Domino反应：一种有效的合成方法已被开发用于螺建设[环戊烷-1,2' - （1' ħ） -萘]通过2-（2-甲酰基乙基）的多米诺迈克尔/迈克尔反应衍生物萘-1- ，4-二酮和硝基烯烃催化的二苯基脯氨醇甲硅烷基醚。
• Discovery of novel naphthoquinone derivatives as inhibitors of the tumor cell specific M2 isoform of pyruvate kinase
  作者：Xianling Ning、Hailong Qi、Ridong Li、Yunqiao Li、Yan Jin、Michael A. McNutt、Junyi Liu、Yuxin Yin

  DOI：10.1016/j.ejmech.2017.06.064

  日期：2017.9

  targeting of PKM2 therefore has potential as strategy for cancer therapy. Here, we report the synthesis and biologic evaluation of novel naphthoquinone derivatives as selective small molecule inhibitors of PKM2. Some target compounds, such as compound 3k, displayed more potent PKM2 inhibitory activity than the reported optimal PKM2 inhibitor shikonin. The well performing compound 3k also showed nanomolar

  丙酮酸激酶M2（PKM2）是在癌细胞中高表达的糖酵解途径的限速酶。癌细胞在很大程度上依赖于PKM2的合成代谢和能量需求，因此，针对PKM2的特异性靶向具有作为癌症治疗策略的潜力。在这里，我们报告新型萘醌衍生物作为PKM2的选择性小分子抑制剂的合成和生物学评估。一些目标化合物（例如化合物3k）比报告的最佳PKM2抑制剂紫草素显示出更强的PKM2抑制活性。性能良好的化合物3k还对具有高表达PKM2的一系列癌细胞系（包括HCT116，Hela和H1299，具有IC 50）具有纳摩尔抗增殖活性。值范围从0.18至1.56μM。此外，化合物3k对癌细胞的细胞毒性比正常细胞高。新型有效的PKM2小分子抑制剂的鉴定不仅为癌症治疗提供了候选化合物，而且还提供了一种工具，可用于深入评估PKM2的功能。