5-amino-8-methyl-4H-benzopyran-4-one | 331683-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-amino-8-methyl-4H-benzopyran-4-one
• 英文别名: 5-Amino-8-methylchromen-4-one
• CAS: 331683-36-4
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: LFXMKJSAAMOJFR-UHFFFAOYSA-N

物化性质

• 熔点：
  141-143 °C
• 沸点：
  352.0±42.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-amino-8-methyl-4H-benzopyran-4-one 在 盐酸 、 sodium nitrite 、 copper(I) bromide 作用下， 以 水 为溶剂， 反应 1.0h， 以50%的产率得到5-bromo-8-methyl-4H-benzopyran-4-one
  参考文献：
  名称：

  一类新的非甾体芳香酶抑制剂：色酮和黄酮衍生物的设计与合成以及对P450酶芳香酶和17α-羟化酶/ C17,20-裂合酶的抑制作用。

  摘要：

  芳香酶（P450arom）是治疗乳腺癌的药理学目标。在本文中，我们报告了该酶的一系列新型（二）苯并吡喃酮类抑制剂的设计，合成和体外生物学评估。新化合物的设计以先前针对一系列非甾体芳香酶抑制剂开发的CoMFA模型为指导。色酮和黄嘌呤核均被视为分子骨架，其功能对于结合芳香酶活性位点至关重要-通过亚甲基与芳香部分相连的杂环（咪唑或1,3,4-三唑）单元和一个H键接受功能（CN，NO（2），Br）位于芳环上，与带有孤对的杂环氮相距合适的距离-并与它们相连。色酮，蒽酮，黄酮衍生物和黄酮衍生物通过常规合成方法由适当的甲基类似物制备。使用人胎盘微粒体和[1β，2β-（3）H]睾丸激素作为标记底物，通过Thompson和Siiteri的方法确定芳香酶抑制活性。还对所有化合物进行了17α-羟化酶/ C17,20-裂合酶（P450 17）的测试，这是一种治疗前列腺疾病的具有治疗意义的酶。x吨酮衍生物22d，e（IC（50）值分别为43和40

  DOI：

  10.1021/jm000955s
• 作为产物：
  描述：

  8-methylchromone 在 Lindlar's catalyst 氢气 、 硝酸 作用下， 以 四氢呋喃 为溶剂， 生成 5-amino-8-methyl-4H-benzopyran-4-one
  参考文献：
  名称：

  一类新的非甾体芳香酶抑制剂：色酮和黄酮衍生物的设计与合成以及对P450酶芳香酶和17α-羟化酶/ C17,20-裂合酶的抑制作用。

  摘要：

  芳香酶（P450arom）是治疗乳腺癌的药理学目标。在本文中，我们报告了该酶的一系列新型（二）苯并吡喃酮类抑制剂的设计，合成和体外生物学评估。新化合物的设计以先前针对一系列非甾体芳香酶抑制剂开发的CoMFA模型为指导。色酮和黄嘌呤核均被视为分子骨架，其功能对于结合芳香酶活性位点至关重要-通过亚甲基与芳香部分相连的杂环（咪唑或1,3,4-三唑）单元和一个H键接受功能（CN，NO（2），Br）位于芳环上，与带有孤对的杂环氮相距合适的距离-并与它们相连。色酮，蒽酮，黄酮衍生物和黄酮衍生物通过常规合成方法由适当的甲基类似物制备。使用人胎盘微粒体和[1β，2β-（3）H]睾丸激素作为标记底物，通过Thompson和Siiteri的方法确定芳香酶抑制活性。还对所有化合物进行了17α-羟化酶/ C17,20-裂合酶（P450 17）的测试，这是一种治疗前列腺疾病的具有治疗意义的酶。x吨酮衍生物22d，e（IC（50）值分别为43和40

  DOI：

  10.1021/jm000955s

文献信息

• Synthesis, X-ray structure, electrochemical properties and cytotoxic effects of new arene ruthenium(II) complexes
  作者：Adam Pastuszko、Karolina Niewinna、Malgorzata Czyz、Andrzej Jóźwiak、Magdalena Małecka、Elzbieta Budzisz

  DOI：10.1016/j.jorganchem.2013.07.020

  日期：2013.11

  organoruthenium(II) complexes with the general formula [(η6-arene)Ru(L)Cl2] (where L = flavone, chromone or benzofuranone derivatives) have been synthesized. All the ligands in the reaction with [(η6-p-cymene)RuCl)2(μ-Cl)2] form monodentate compounds, which were fully characterized by elemental analysis, MS, UV–Vis, IR and NMR spectroscopy. The molecular structure of one of the complexes [(η6-p-cymen

  与通式A一系列新型半夹心有机钌（II）配合物[（η 6 -arene）的Ru（L）氯2 ]（其中L =黄酮，色酮或苯并呋喃酮的衍生物）已被合成。与反应的所有配体[（η 6 - p -cymene）的RuCl）2（μ-Cl）的2 ]形式的单齿化合物，其被充分表征通过元素分析，质谱，紫外-可见光，IR和NMR光谱。复合物中的一个的分子结构[（η 6 - p -cymene）的Ru（7-氨基-3- ħ苯并呋喃-1-酮- κ 1 -N）氯2通过X射线晶体学测定。通过循环伏安法监测复合物的氧化还原性质。还已经在几种黑素瘤和白血病细胞系上评估了所有获得的化合物的细胞毒性。
• The synthesis, lipophilicity and cytotoxic effects of new ruthenium(II) arene complexes with chromone derivatives
  作者：Adam Pastuszko、Kinga Majchrzak、Malgorzata Czyz、Bogumiła Kupcewicz、Elzbieta Budzisz

  DOI：10.1016/j.jinorgbio.2016.02.020

  日期：2016.6

  A series of arene ruthenium(II) complexes with the general formula [(eta6-arene)Ru(L)X2] (where arene=p-cymene, benzene, hexamethylbenzene or mesitylene, L=aminoflavone or aminochromone derivatives and X=Cl, I) were synthesized and characterized by elemental analysis, MS, IR and 1H NMR spectroscopy. The stability of the selected complexes was assessed by UV-Vis spectroscopy in 24-hour period. The lipophilicity

  一系列具有通式[（eta6-arene）Ru（L）X2]的芳烃钌（II）配合物（其中芳烃=对苯甲基，苯，六甲基苯或均三甲苯，L =氨基黄酮或氨基色酮衍生物，X = Cl， I）合成并通过元素分析，MS，IR和1H NMR光谱进行表征。通过UV-Vis光谱在24小时内评估所选复合物的稳定性。通过摇瓶法测定合成的复合物的亲脂性，并在体外对患者来源的黑素瘤人群进行细胞毒性评估。针对黑色素瘤细胞最活跃的复合物包含7-氨基黄酮和6-氨基黄酮作为配体。确定了所有获得的化合物的细胞毒性与其logP值之间的关系，并通过观察到的两种不同模式对其进行了简要分析。
• Synthesis, structure, electrochemical properties, cytotoxic effects and antioxidant activity of 5-amino-8-methyl-4H-benzopyran-4-one and its copper(II) complexes
  作者：Magdalena Grażul、Aleksander Kufelnicki、Magdalena Wozniczka、Ingo-Peter Lorenz、Peter Mayer、Andrzej Jóźwiak、Malgorzata Czyz、Elzbieta Budzisz

  DOI：10.1016/j.poly.2011.09.003

  日期：2012.1

  The chromone derivative 5-amino-8-methyl-4H-benzopyran-4-one (ligand) (1) has been used to obtain a series of Cu(II) complexes 2-4 as potential anticancer compounds. The molecular structures of ligand 1 and its Cu(II) complex 3 have been determined by X-ray crystallography. The cytotoxicity of all obtained compounds has been evaluated on melanoma A375 cell line. The ability of compounds 1-4 to take part in redox reactions and their antioxidant activity have been studied. (C) 2011 Elsevier Ltd. All rights reserved.
• The synthesis, spectroscopic properties and X-ray structure of Zn(II) complexes with amino derivatives of chromone
  作者：Bogumiła Kupcewicz、Magdalena Grazul、Ingo-Peter Lorenz、Peter Mayer、Elzbieta Budzisz

  DOI：10.1016/j.poly.2011.01.033

  日期：2011.4

  Three new Zn(II) complexes containing the ligands 5-amino-8-methyl-4H-chromen-4-one (1), 6- or 7-amino-2-phenyl-4H-chromen-4-one (2,3) were prepared. The new synthesised compounds were characterised by IR, H-1 NMR and MS spectroscopy. The crystal structure of complex 4 was determined with the use X-ray diffraction. The Zn(II) centre of 4 is linked by two chlorido and two N-bound aminochromone ligands, 1, in a strongly distorted tetrahedral configuration with the dissymetric point group C-2. The protonation constants of the ligands 1, 2 and 3 corresponded to 3.68, 3.88 and 6.83, respectively. The stability constants of the Zn(II) complexes were calculated from the potentiometric titration data. The complexes were found to have the formulae ML and ML2 for ligands 1 and 2, and ML for ligand 3. Fluorescence spectroscopic properties were also studied; the strongest fluorescence in solution was exhibited by complex 6. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis, structure, physico-chemical and biological properties of metal(II) complexes with 5-amino-8-methyl-4H-benzopyran-4-one
  作者：Magdalena Grazul、Roland Sigel、Caroline Maake、Emina Besic-Gyenge、Ingo-Peter Lorenz、Peter Mayer、Malgorzata Czyz、Elzbieta Budzisz

  DOI：10.1016/j.poly.2013.08.071

  日期：2014.1

  Two new complexes of a previously obtained chromone derivative, 5-amino-8-methyl-4H-benzopyran-4-one (ligand 1), with the Co(II) (4) and Pd(II) (5) ions were synthesized and characterized by elemental analysis, IR and mass spectroscopy. The previously characterized Cu(II) complexes (2 and 3) and the newly obtained complexes of ligand 1 with Pd(II) and Co(II) have been tested as potential anticancer compounds. The molecular structure of 5 has been determined by X-ray crystallography. Biological properties, such as cytotoxicity against several cancer cell lines, the influence of the obtained compounds on the DNA structure by CD spectroscopy and agarose gel electrophoresis, have been evaluated. Also some physico-chemical properties, such as lipophilicity and stability in the aqueous solution, were tested. (C) 2013 Elsevier Ltd. All rights reserved.