6,7-dihydroxy-2-(3',4'-dihydroxyphenyl)naphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6,7-dihydroxy-2-(3',4'-dihydroxyphenyl)naphthalene
• 英文别名: 6-(3,4-Dihydroxyphenyl)naphthalene-2,3-diol
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: RHRGPVYNLSTBIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3,4-二甲氧基苯基)乙醛 在 盐酸 、 三溴化硼 作用下， 以 1,4-二氧六环 为溶剂， 生成 6,7-dihydroxy-2-(3',4'-dihydroxyphenyl)naphthalene
  参考文献：
  名称：

  大麻素与三溴化硼的反应

  摘要：

  用三溴化硼处理芳基乙醛1，可得到2-苯基萘2或1,2,9,10-四氢-1,9-环氧二苯并[a，e]环辛烯3通过串联的羟醛缩合-分子内Friedel-Crafts环化反应或缩合反应得到。在O-位置分别进行两次Friedel-Crafts烷基化。在所有情况下，都会发生甲氧基的完全脱甲基。

  DOI：

  10.1016/s0040-4039(98)01895-4

文献信息

• Structure-Activity Relationship of Synthetic 2-Phenylnaphthalenes with Hydroxyl Groups that Inhibit Proliferation and Induce Apoptosis of MCF-7 Cancer Cells
  作者：Chi-Fen Chang、Ci-Yi Ke、Yang-Chang Wu、Ta-Hsien Chuang

  DOI：10.1371/journal.pone.0141184

  日期：——

  In this study, six 2-phenylnaphthalenes with hydroxyl groups were synthesized in high yields by the demethylation of the corresponding methoxy-2-phenylnaphthalenes, and one 2-phenylnaphthalene with an amino group was obtained by hydrogenation. All of the 2-phenylnaphthalene derivatives were evaluated for cytotoxicity, and the structure-activity relationship (SAR) against human breast cancer (MCF-7) cells was also determined. The SAR results revealed that cytotoxicity was markedly promoted by the hydroxyl group at the C-7 position of the naphthalene ring. The introduction of hydroxyl groups at the C-6 position of the naphthalene ring and the C-4' position of the phenyl ring fairly enhanced cytotoxicity, but the introduction of a hydroxyl group at the C-3' position of the phenyl ring slightly decreased cytotoxicity. Overall, 6,7-dihydroxy-2-(4'-hydroxyphenyl)naphthalene (PNAP-6h) exhibited the best cytotoxicity, with an IC50 value of 4.8 μM against the MCF-7 cell line, and showed low toxicity toward normal human mammary epithelial cells (MCF-10A). PNAP-6h led to cell arrest at the S phase, most likely due to increasing levels of p21 and p27 and decreasing levels of cyclin D1, CDK4, cyclin E, and CDK2. In addition, PNAP-6h decreased CDK1 and cyclin B1 expression, most likely leading to G2/M arrest, and induced morphological changes, such as nuclear shrinkage, nuclear fragmentation, and nuclear hypercondensation, as observed by Hoechst 33342 staining. PNAP-6h induced apoptosis, most likely by the promotion of Fas expression, increased PARP activity, caspase-7, caspase-8, and caspase-9 expression, the Bax/Bcl-2 ratio, and the phosphorylation of p38, and decreased the phosphorylation of ERK. This study provides the first demonstration of the cytotoxicity of PNAPs against MCF-7 cells and elucidates the mechanism underlying PNAP-induced cytotoxicity.

  本研究通过相应的甲氧基-2-苯基萘的去甲基化高产率合成了六种带有羟基的2-苯基萘，并通过氢化得到了一种带有氨基的2-苯基萘。评估了所有 2-苯基萘衍生物的细胞毒性，并测定了针对人乳腺癌 (MCF-7) 细胞的构效关系 (SAR)。 SAR结果表明，萘环C-7位上的羟基显着增强了细胞毒性。萘环C-6位和苯环C-4'位羟基的引入相当增强了细胞毒性，但苯环C-3'位羟基的引入略有降低细胞毒性。总体而言，6,7-二羟基-2-(4'-羟苯基)萘(PNAP-6h)表现出最好的细胞毒性，对MCF-7细胞系的IC50值为4.8 μM，对正常人乳腺表现出较低的毒性上皮细胞（MCF-10A）。 PNAP-6h 导致细胞停滞在 S 期，很可能是由于 p21 和 p27 水平增加以及细胞周期蛋白 D1、CDK4、细胞周期蛋白 E 和 CDK2 水平降低。此外，PNAP-6h 降低了 CDK1 和细胞周期蛋白 B1 的表达，很可能导致 G2/M 期停滞，并诱导形态学变化，如核收缩、核碎裂和核高浓缩，如 Hoechst 33342 染色所观察到的。 PNAP-6h 诱导细胞凋亡，最有可能是通过促进 Fas 表达、增加 PARP 活性、caspase-7、caspase-8 和 caspase-9 表达、Bax/Bcl-2 比率和 p38 磷酸化，并降低ERK 磷酸化。这项研究首次证明了 PNAP 对 MCF-7 细胞的细胞毒性，并阐明了 PNAP 诱导细胞毒性的机制。
• 一种绿色、简便的6-(3,4-二羟基苯基)-2,3-萘二醇制备方法
  申请人：昆明理工大学

  公开号：CN114181049A

  公开（公告）日：2022-03-15

  本发明涉及一种绿色、简便的6‑(3,4‑二羟基苯基)‑2,3‑萘二醇制备方法，具体地，本发明的制备方法使用植物提取物表儿茶素和乙二酸为原料，具有绿色、天然可再生的特点，同时本发明的制备方法操作简单、条件温和，只需一步，原子利用率高，避免过多废物排放污染环境，绿色环保，符合绿色化学的发展理念。
• New 2-arylnaphthalenediols and triol inhibitors of HIV-1 integrase—Discovery of a new polyhydroxylated antiviral agent
  作者：Cédric Maurin、Cédric Lion、Fabrice Bailly、Nadia Touati、Hervé Vezin、Gladys Mbemba、Jean François Mouscadet、Zeger Debyser、Myriam Witvrouw、Philippe Cotelle

  DOI：10.1016/j.bmc.2010.05.059

  日期：2010.7

  A series of 13 hydroxylated 2-arylnaphthalenes have been synthesized and evaluated as HIV-1 integrase inhibitors. 7-(3,4,5-Trihydroxyphenyl) naphthalene-1,2,3-triol 1c revealed chemical instability upon storage, leading to the isolation of a dimer 5c which was also tested. In the 2-arylnaphthalene series, all compounds were active against HIV-1 IN with IC50' s within the 1-10 lM range, except for 1c and 5c which displayed submicromolar activity. Antiviral activity against HIV-1 replication was measured on 1b-c and 5c. Amongst the tested molecules, only 5c was found to present antiviral properties with a low cytotoxicity on two different cell lines. (C) 2010 Elsevier Ltd. All rights reserved.
• POLYMERIZABLE COMPOUND, POLYMERIZABLE COMPOSITION AND LIQUID CRYSTAL DISPLAY DEVICE
  申请人：JNC CORPORATION

  公开号：US20150102259A1

  公开（公告）日：2015-04-16

  An object is to provide a liquid crystal compound having high polymerization reactivity, a high conversion ratio and high solubility in a liquid crystal composition, a polymerizable composition containing the compound, a liquid crystal composite prepared using the composition, and a liquid crystal display device having the composite. A solution is a polymerizable compound represented by formula (1). In formula (1), P 1 and P 2 are identically group (P-1), (P-2) or (P-3), and in formula (P-1), M is hydrogen, fluorine, —CH 3 or —CF 3 ; S 1 and S 2 are a single bond, alkylene having 1 to 6 carbons or the like; a1, a2 and b1 are 0, 1, 2, 3 or 4, and a sum of al and a2 is 4; ring A 1 is naphthalene, anthracene or phenanthrene; and ring A 2 is cyclohexyl, phenyl, naphthyl, anthracenyl or phenanthrenyl; and Z 1 is a single bond, —CO—, —COO— or the like.
• US9394482B2
  申请人：——

  公开号：US9394482B2

  公开（公告）日：2016-07-19

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