4-[(3,4-二甲基-1,2-恶唑-5-基)氨基]萘-1,2-二酮 | 81620-95-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-[(3,4-二甲基-1,2-恶唑-5-基)氨基]萘-1,2-二酮
• 英文名称: N-(3,4-dimethyl-5-isoxazolyl)-4-amino-1,2-naphthoquinone
• 英文别名: 4-N-(3,4-dimethyl-5-isoxazolyl)-1,2-naphthoquinone；4-[(3,4-dimethyl-1,2-oxazol-5-yl)amino]naphthalene-1,2-dione
• CAS: 81620-95-3
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: VNVKTYUMZHBALO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  72.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[(3,4-二甲基-1,2-恶唑-5-基)氨基]萘-1,2-二酮 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以93%的产率得到N-(3,4-dimethyl-5-isoxazolyl)-4-amino-1,2-naphthoquinone-2-one oxime
  参考文献：
  名称：

  Synthesis, antiprotozoal and cytotoxic activities of new N-(3,4-dimethyl-5-isoxazolyl)-1,2-naphthoquinone-4-amino derivatives

  摘要：

  Three derivatives of N-(3,4-dimethyl-5-isoxazolyl)-1,2-naphthoquinone-4-amino (1), a compound which exhibits significant activity against Trypanosoma cruzi and Plasmodium falciparum but with cytotoxicity toward murine L-6 cells, were synthesized with the aim of ameliorating its cytotoxicity. The in vitro antiprotozoal and cytotoxic activities of the synthesized compounds were evaluated against T. cruzi, Trypanosoma brucei rhodesiense, P. falciparum and murine L-6 cells. The hydroxymethyl (2) and the oxime (3) derivatives were active against T. cruzi, with IC50 values in a range comparable to those of 1 (IC50: 0.65 microg/ml) and benznidazole (IC50: 0.56 microg/ml) while the carboxymethyloxime (4) was inactive. Compounds 2 and 3 were cytotoxic toward L-6 cells, with IC50 values identical to that of 1 (IC50: 0.50 microg/ml). The results did not support the suggestion that 2 and 3 may be used as prodrugs of 1.

  DOI：

  10.1016/j.farmac.2004.03.003
• 作为产物：
  描述：

  2-(3,4-dimethyl-5-isoxazolylamine)-N-(3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinone-4-imine 在 水 作用下， 生成 4-[(3,4-二甲基-1,2-恶唑-5-基)氨基]萘-1,2-二酮
  参考文献：
  名称：

  异恶唑。六：新型萘醌胺在酸性水溶液中的化学稳定性。

  摘要：

  研究了N-（3,4-二甲基-5-异恶唑基）-4-氨基-1,2-萘醌化学降解的某些方面，其与pH和温度的关系。在酸性和中性pH下，鉴定出四个主要降解产物：2-羟基-1,4-萘醌，2-丁酮，氨和羟胺。对于本研究中使用的缓冲液种类，未观察到明显的缓冲液影响。pH速率曲线显示出特定的酸催化作用，这在pH值小于3.5时很重要，在pH 1.10时的拐点对应于pKa值。从阿累尼乌斯曲线图中，发现活化能为17.8 +/- 0.3 kcal / mol。

  DOI：

  10.1002/jps.2600790820

文献信息

• Isoxazoles V: Chemical Stability of Diisoxazolylnaphthoquinone in Aqueous Solution
  作者：Marcela R. Longhi、Maria M. De Bertorello、Margarita C. Briñon

  DOI：10.1002/jps.2600780513

  日期：1989.5

  pseudo-first-order kinetics with respect to the concentration of 1. The pH-rate profile was linear with slopes -1 and +1 in acid and alkaline pH, respectively, becoming pH independent in the region of maximum stability from pH 4.5 to 10.0. Neither primary salt effects nor buffer catalysis was observed due to the buffer species employed.

  广泛研究了2-（3,4-二甲基-5-异恶唑基胺）-N-（3,4-二甲基-5-异恶唑基）-1,4-萘醌-4-亚胺（1）的水解降解pH值和在不同温度下的变化。通过反相HPLC测定降解速率，并观察到其相对于1的浓度遵循拟一级动力学。pH速率曲线在酸性和碱性pH值下分别呈-1和+1斜率线性关系。在pH值从4.5到10.0的最大稳定性范围内变为pH无关。由于所使用的缓冲剂种类，未观察到伯盐效应或缓冲剂催化作用。
• COMPOSITION FOR INHIBITING OR PREVENTING THE FORMATION OF A BIOFILM
  申请人：Oystershell NV

  公开号：EP1796656A2

  公开（公告）日：2007-06-20
• Composition for Inhibiting or Preventing the Formation of a Biofilm
  申请人：Rossel Bart

  公开号：US20070258913A1

  公开（公告）日：2007-11-08

  Compounds for inhibiting and/or preventing the formation of a biofilm are disclosed. The compounds are an anthraquinone and/or a naphtoquinone, stereoisomeric forms, racemic mixtures, metabolites, esters or salts thereof, or mixtures thereof, and/or at least one plant extract including the compound or active fraction thereof. Compositions containing the compounds such as oral health products and methods of using the products in a method to prevent or inhibit biofilm formation are also disclosed. Preferred compositions include emodin and/or plant extracts from Rheum sp.
• US7691418B2
  申请人：——

  公开号：US7691418B2

  公开（公告）日：2010-04-06
• [EN] COMPOSITION FOR INHIBITING OR PREVENTING THE FORMATION OF A BIOFILM<br/>[FR] COMPOSITION PERMETTANT DE BLOQUER OU D'EMPECHER LA FORMATION D'UN FILM BIOLOGIQUE
  申请人：OYSTERSHELL NV

  公开号：WO2006029893A2

  公开（公告）日：2006-03-23

  The present invention provides the use of a compound selected from the group comprising an anthraquinone and a naphtoquinone, stereoisomeric forms, racemic mixtures, metabolites, esters or salts thereof, or mixtures thereof, and/or of at least one plant extract or active fraction thereof comprising said compound for preventing and/or inhibiting biofilm formation. The present invention further relates to compositions for preventing and/or inhibiting the formation of a biofilm, oral health products and a method for preventing and/or inhibiting biofilm formation.