2-amino-3-(3-methoxyphenyl)naphthalene-1,4-dione | 1134319-87-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-amino-3-(3-methoxyphenyl)naphthalene-1,4-dione
• 英文别名: 2-amino-3-(3-methoxylphenyl)-1,4-naphthoquinone
• CAS: 1134319-87-1
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: GCYILLQQGFAJJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  69.39
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-amino-3-(3-methoxyphenyl)naphthalene-1,4-dione 、 苯甲酰氯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 N-(3-(3-methoxyphenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzamide
  参考文献：
  名称：

  Synthesis and evaluation of Hsp90 inhibitors that contain the 1,4-naphthoquinone scaffold

  摘要：

  High-throughput screening of a library of diverse molecules has identified the 1,4-naphthoquinone scaffold as a new class of Hsp90 inhibitors. The synthesis and evaluation of a rationally-designed series of analogues containing the naphthoquinone core scaffold has provided key structure-activity relationships for these compounds. The most active inhibitors exhibited potent in vitro activity with low micromolar IC50 values in anti-proliferation and Her2 degradation assays. In addition, 3g, 12, and 13a induced the degradation of oncogenic Hsp90 client proteins, a hallmark of Hsp90 inhibition. The identification of these naphthoquinones as Hsp90 inhibitors provides a new scaffold upon which improved Hsp90 inhibitors can be developed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.064
• 作为产物：
  描述：

  1,4-萘醌 在 palladium diacetate 、 N-碘吗啉氢碘酸盐 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 2-amino-3-(3-methoxyphenyl)naphthalene-1,4-dione
  参考文献：
  名称：

  P2X7 receptor inhibition by 2-amino-3-aryl-1,4-naphthoquinones

  摘要：

  Extracellular ATP activates purinergic receptors such as P2X7, cationic channels for Ca2+, K+, and Na+. There is robust evidence of the involvement of these receptors in the immune response, so P2X7 receptors (P2X7R) are considered a potential therapeutic target for the development of anti-inflammatory drugs. Although there are many studies of the anti-inflammatory properties of naphthoquinones, these molecules have not yet been explored as P2X7 antagonists. In previous work, our group prepared 3-substituted (halogen or aryl) 2-hydroxy-1,4-naphthoquinones and studied their action on P2X7R. In this paper, eight 2-amino-3-aryl-1,4-naphthoquinones were evaluated to identify the inhibitory activity on P2X7R and the toxicological profile. Three analogues (AD-4CN, AD-4Me, and AD-4F) exhibited reduced toxicity for mammalian cells with CC50 values higher than 500 mu M. These three 3-substituted 2-amino-1,4-naphthoquinones inhibited murine P2X7R (mP2X7R) in vitro. However, the analogues AD-4CN and AD-4Me showed low selectivity index values. AD-4F inhibited both mP2X7R and human P2X7R (hP2X7R) with IC50 values of 0.123 and 0.93 mu M, respectively. Additionally, this analogue exhibited higher potency than BBG at inhibiting the ATP-induced release of IL-1 beta in vitro. Carrageenaninduced paw edema in vivo was reversed for AD-4F with an ID50 value of 11.51 ng/kg. Although AD-4F was less potent than previous 3-substituted (halogen or aryl) 2-hydroxy-1,4-naphthoquinones such as AN-04 in vitro, this 3-substituted 2-amino-1,4-naphthoquinone revealed higher potency in vivo to reduce the edematogenic response. In silico analysis suggests that the binding site of the novel 2-amino-3-aryl-1,4-naphthoquinone derivatives, including all the tautomeric forms, is located in the pore area of the hP2X7R model. Based on these results, we considered AD-4F to be a satisfactory P2X7R inhibitor. AD-4F might be used as a scaffold structure to design a novel series of inhibitors with potential inhibitory activity on murine (mP2X7R) and human (hP2X7R) P2X7 receptors.

  DOI：

  10.1016/j.bioorg.2020.104278

文献信息

• Transition metal mediated selective C vs N arylation of 2-aminonaphthoquinone and its application toward the synthesis of benzocarbazoledione
  作者：Polu Ashok、Andivelu Ilangovan

  DOI：10.1016/j.tetlet.2017.10.075

  日期：2018.1

  Selective C vs N-arylation of 2-aminonaphthoquinone was achieved using different transition metal salts and arylboronic acids. Mn(OAc)(3)center dot 2H(2)O provided C-arylated product whereas NiCl2 center dot 6H(2)O and Cu (OAc)(2)center dot H2O provided N-mono arylated and N,N-diarylated products respectively. Usefulness of the C and N arylated product was demonstrated by converting it into benzocarbazoledione. (C) 2017 Elsevier Ltd. All rights reserved.