2-amino-3-phenyl-1,4-naphthoquinone | 56176-17-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-amino-3-phenyl-1,4-naphthoquinone
• 英文别名: 2-amino-3-phenylnaphthalene-1,4-dione；1,4-Naphthalenedione, 2-amino-3-phenyl-
• CAS: 56176-17-1
• 化学式: C₁₆H₁₁NO₂
• 分子量: 249.269
• InChiKey: GFUXSPXAFRJOOL-UHFFFAOYSA-N

物化性质

• 熔点：
  178.5-179.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  432.8±45.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 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：
  60.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-3-phenyl-1,4-naphthoquinone 以2%的产率得到
  参考文献：
  名称：

  FORRESTER A. R.; INGRAM A. S.; JOHN I. L.; THOMSON R. H., J. CHEM. SOC. PERKIN TRANS. PART I, , 1975, NO 12, 1115-1120

  摘要：

  DOI：
• 作为产物：
  描述：

  萘酚 在 N-溴代丁二酰亚胺(NBS) 、 氨 、 palladium diacetate 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-amino-3-phenyl-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis, reactive oxygen species generation and copper-mediated nuclease activity profiles of 2-aryl-3-amino-1,4-naphthoquinones

  摘要：

  Here we report a series of 2-aryl-3-amino-1,4-naphthoquinones that generated reactive oxygen species (ROS) such as superoxide and hydrogen peroxide upon incubation in pH 7.4 under ambient aerobic conditions. ROS generation from these compounds was sensitive to structural modifications at the 3-amino position and a 2-aryl substituent promoted ROS generation. A number of these compounds were found to induce DNA damage in the presence of Cu(II) without any added reducing agent. Our data suggests that 2-aryl-3-amino-1,4-naphthoquinones' propensity to produce ROS correlated well with its DNA damage inducing ability. 2-Phenyl-3-pyrrolid-1-yl-1,4-naphthoquinone (22) was found to damage DNA at 1 mu M suggesting that these compounds may have therapeutic relevance in targeting cancers which over-express Cu(II) (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.009

文献信息

• Synthesis, characterization and biological activities of 3-aryl-1,4-naphthoquinones – green palladium-catalysed Suzuki cross coupling
  作者：Aline da R. Louvis、Nayane A. A. Silva、Felipe S. Semaan、Fernando de C. da Silva、Gabriela Saramago、Laís C. S. V. de Souza、Bruno L. A. Ferreira、Helena C. Castro、Juliana P. Salles、André L. A. Souza、Robson X. Faria、Vitor F. Ferreira、Daniela de L. Martins

  DOI：10.1039/c6nj00872k

  日期：——

  2-hydroxy-3-iodo-1,4-naphthoquinone and boronic acids were employed to prepare several 2-hydroxy-3-aryl-1,4-naphthoquinones in aqueous conditions using microwave irradiation or conventional heating. Because of the biological activities of quinones, which are related to their ability to accept electrons to form semiquinones and hydroquinones, the electrochemical behaviour of the synthesized molecules was investigated

  醌是存在于多种天然产物或合成生物活性分子中的重要支架。芳基化是完成结构修饰的重要策略，从而导致新的潜在候选药物被用作药物。在目前的工作中，采用钯催化的2-羟基-3-碘-1,4-萘醌与硼酸之间的无钯，无膦的Suzuki偶联反应制备了几种2-羟基-3-芳基-1,4。 -萘醌在水性条件下使用微波辐射或常规加热。由于醌的生物活性与它们接受电子形成半醌和对苯二酚的能力有关，因此对合成分子的电化学行为进行了研究。Osiris和Molinspiration化学信息学计划，利用在计算机分析中，这意味着这些萘醌是候选药物，体外抗真菌和锥虫活性测试的结果进一步证实了这些萘醌。我们的体外数据表明，针对白色念珠菌ATCC 24433菌株的MIC值为8，微克mL -1，针对克氏锥虫锥虫病的锥虫杀虫活性，EC 50为0.67μM。
• Synthesis of Carbazolequinones by Formal [3 + 2] Cycloaddition of Arynes and 2-Aminoquinones
  作者：Jian Guo、I. N. Chaithanya Kiran、R. Santhosh Reddy、Jiangsheng Gao、Meiqiong Tang、Yuyin Liu、Yun He

  DOI：10.1021/acs.orglett.6b01090

  日期：2016.5.20

  A formal cycloaddition reaction for the synthesis of biologically and pharmaceutically important carbazolequinones via the annulation of aminoquinones with arynes has been developed. This practical and metal-free cascade reaction proceeds through successive C–C/C–N bond formations. Moreover, this novel method has been utilized for the concise synthesis of bioactive murrayaquinone A and koeniginequinone

  已经开发了一种正式的环加成反应，用于通过氨基醌与芳烃的环合反应合成生物学上和药学上重要的咔唑醌。这种实用且无金属的级联反应是通过连续的C–C / C–N键形成而进行的。此外，该新方法已被用于简明合成生物活性的墨瑞亚醌A和甲烯乙醌B及其类似物。
• 3-Aryliodonio-1,4-naphthoquinone-2-imides: A new class of aryliodonium 1,4 dipoles
  作者：Ioannis Papoutsis、Spyros Spyroudis、Anastasios Varvoglis

  DOI：10.1016/0040-4039(95)02278-3

  日期：1996.2

  The synthesis of a new class of zwitterionic aryliodonium compounds from 2-amino-1,4-naphthoquinone and [(hydroxy) (tosyloxy)iodo]arenes is described. These dipoles exhibit an interesting reactivity under thermal and photochemical conditions.

  描述了由2-氨基-1,4-萘醌和[（羟基）（甲苯磺酰氧基）碘]芳烃合成的新型两性离子芳基碘鎓化合物。这些偶极子在热和光化学条件下表现出令人感兴趣的反应性。
• Aryliodonium Derivatives of 2-Amino-1,4-quinones : Preparation and Reactivity
  作者：Ioannis Papoutsi、Spyros Spyroudis、Anastasios Varvoglis、Catherine P. Raptopoulou

  DOI：10.1016/s0040-4020(97)00270-6

  日期：1997.4

  [(hydroxy)(tosyloxy)iodo]arenes affords stable 2-amino-3-aryliodonio-1,4-quinones in high yields. The latter, upon treatment with alkali, are converted to the corresponding zwitterionic 3-aryliodonio-1,4-quinone-2-imides. This new class of compounds exhibits an interesting reactivity: upon heating, aryl migration from iodine to nitrogen is observed, while photochemical reaction with aromatic compounds and 2,3-dihydrofuran

  2-氨基-1,4-醌与[（羟基）（甲苯磺酰氧基）碘]芳烃的反应以高收率提供了稳定的2-氨基-3-芳基碘_1,4-醌。在用碱处理后，后者被转化为相应的两性离子的3-芳基碘-1，4-醌-2-酰亚胺。这类新化合物表现出有趣的反应性：加热后，观察到芳基从碘迁移到氮，而与芳族化合物和2,3-二氢呋喃的光化学反应产生取代产物。醇钠对这些两性离子的亲核攻击导致醌环的打开，从而提供了合成上令人感兴趣的多功能产品。©1997爱思唯尔科学有限公司。
• INHIBITORS OF THE MITF MOLECULAR PATHWAY
  申请人：THE GENERAL HOSPITAL CORPORATION

  公开号：US20160130222A1

  公开（公告）日：2016-05-12

  Provided herein are compounds of the formula (IV) as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful as MITF inhibitors, MITF pathway inhibitors and for the treatment of cancer.

  本文提供的是公式（IV）的化合物及其药学上可接受的盐，其中取代基如规范中所披露的那样。这些化合物及其含有的药物组合物可用作MITF抑制剂、MITF通路抑制剂以及治疗癌症的药物。