4-((3,4-dimethyl-5-isoxazolyl)imino)-2-hydroxy-1(4H)-Naphthalenone | 81620-91-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-((3,4-dimethyl-5-isoxazolyl)imino)-2-hydroxy-1(4H)-Naphthalenone
• 英文别名: 2-hydroxy-N-(3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinone 4-imine；2-hydroxy-N-(3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinone-4-imine；2-hydroxy-N-(3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinon-4-imine
• CAS: 81620-91-9
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: FEPDERIRTCSDKL-FOWTUZBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  75.69
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-((3,4-dimethyl-5-isoxazolyl)imino)-2-hydroxy-1(4H)-Naphthalenone 在 羟胺 作用下， 以 乙醇 为溶剂， 以73%的产率得到2-hydroxy-N-(3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinone 4-imine 1-oxime
  参考文献：
  名称：

  2-羟基-AK3,4-二甲基-5-异恶唑基）-1,4-萘醌4-1胺衍生物的合成及一些理化性质

  摘要：

  摘要合成了难溶性药物2-羟基-AA（3,4-二甲基-5-异恶唑基} -1,4-萘醌4-亚胺（3）的衍生物，试图提高其理化性质。 。这些新化合物通过包括迭代nmR方法（LAOCOON III程序）在内的光谱方法进行了表征，其理化性质如溶解度，相对亲脂性（/？M）

  DOI：

  10.1002/jps.2600830313
• 作为产物：
  描述：

  3-bromo-2-hydroxy-N-(3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinon-4-imine 在 乙醇 作用下， 生成 4-((3,4-dimethyl-5-isoxazolyl)imino)-2-hydroxy-1(4H)-Naphthalenone
  参考文献：
  名称：

  一阶导数分光光度法测定乙醇中3-溴-2-羟基N-（3,4-二甲基-5-异恶唑基）-1,4-萘醌-4-亚胺的稳定性

  摘要：

  一种新的潜在的杀菌剂3-溴-2-羟基-N-（3,4-二甲基-5-异恶唑基）-1,4-萘醌-4-亚胺（2）的降解动力学（95％）在室温和避光条件下，在35至50摄氏度之间研究了乙醇。分离出分解产物，鉴定为2-羟基-N-（3，4-二甲基-5-异恶唑基）-1，4-萘醌-4-亚胺（1）。报道了一种使用“过零”一阶导数分光光度法在1存在下测定2的简单，快速和稳定性指示方法。使用完整药物及其分解产物的合成混合物并通过对校准数据进行统计分析，证明了该方法的有效性。2的降解反应的伪一阶常数 从残余浓度对数与时间的线性图获得的结果，在室温和光照条件下，计算得出的活化参数Ea，δH不等于和delta S不等于。还评估了2的体外抗菌活性。

  DOI：

  10.1002/jps.2600831118

文献信息

• Isoxazoles. 8. Preformulation Studies of an Isoxazolylnaphthoquinone Derivative
  作者：Marcela R. Longhi、Maria M. De Bertorello、Gladys E. Granero

  DOI：10.1002/jps.2600830314

  日期：1994.3

  The degradation kinetics of 2-hydroxy-N-(3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinone 4-imine (1) in a 25% solution of ethyl alcohol in water has been studied. The rate constants were observed to follow pseudo-first-order kinetics in all cases. The pH-rate profile indicated a negligible decomposition at pH values higher than its pKa2 value [5.4 +/- 0.14 (*n = 6)]. Un-ionized 1 was subject to specific

  研究了在25％的乙醇水溶液中2-羟基-N-（3,4-二甲基-5-异恶唑基）-1,4-萘醌4-亚胺（1）的降解动力学。在所有情况下，均观察到速率常数遵循伪一级动力学。pH速率曲线表明，在高于其pKa2值[5.4 +/- 0.14（* n = 6）]的pH值下，分解可忽略不计。未电离的1受到特定的酸催化作用。离子强度不影响药物的稳定性。这些数据可用于开发药物的稳定口服液剂型。
• Linares; Longhi, Pharmazie, 2003, vol. 58, # 1, p. 32 - 37
  作者：Linares、Longhi

  DOI：——

  日期：——
• Antibacterial effect of 2-hydroxy-N-(3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinone-4-imine onStaphylococcus aureus
  作者：P. Bogdanov、I. Albesa、N. R. Sperandeo、C. Luna、M. M. de Bertorello

  DOI：10.1007/bf01969737

  日期：1996.6

  The mechanism by which a new naphthoquinone derivative, the 2-hydroxy-N-(3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinone-4-imine (INQI-E) has antibacterial effect against Staphylococcus aureus was studied. The interaction of INQI-E with the bacteria was followed by absorption spectroscopy at 323 and 490 nm. The absorption band of INQI-E at 490 nm undergoes a hypochromic shift with a decrease of intensity. This effect was found to be reversible by oxygenation during the first hours of incubation. The participation of an oxidation-reduction process related to the respiratory chain was demonstrated by oxygen consumption. An increase in O-2 uptake and inhibition of S. aureus growth was observed. Experiments with three inhibitors of the respiratory chain demonstrated that the pathway induced by INQI-E was antimycin-resistant and KCN- and salicylhydroxamic acid (SHAM)-sensitive, which suggests that INQI-E is capable of diverting the normal electron flow to an alternate superoxide-producing route. On the other hand, experiments with Tiron, a specific scavenger of superoxide, hindered the effect of INQI-E against S. aureus, indicating that the inhibitory growth effect of this quinone-imine is mainly due to the production of the cytotoxic superoxide radical.
• Dabbene V. G., Brino M. C., de Bertorello M. M., Org. Prep. and Proced. Int, 27 (1995) N 1, S 75-80
  作者：Dabbene V. G., Brino M. C., de Bertorello M. M.

  DOI：——

  日期：——
• Synthesis and Some Physicochemical Properties of 2-Hydroxy-AK3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinone 4-1mine Derivatives
  作者：Norma R. Sperandeo、María M. De Bertorello、Margarita C. Briñón

  DOI：10.1002/jps.2600830313

  日期：1994.3

  Abstract Some derivatives of 2-hydroxy-AA(3,4-dimethyl-5-isoxazol- yl}-1,4-naphthoquinone 4-imine (3), a poorly soluble drug, were synthesized in an attempt to improve their physicochemical properties. The new compounds were characterized by spectroscopic methods including an iterative nmR method (the LAOCOON III program). The physicochemical properties such as solubility, relative lipophilicity (/

  摘要合成了难溶性药物2-羟基-AA（3,4-二甲基-5-异恶唑基} -1,4-萘醌4-亚胺（3）的衍生物，试图提高其理化性质。 。这些新化合物通过包括迭代nmR方法（LAOCOON III程序）在内的光谱方法进行了表征，其理化性质如溶解度，相对亲脂性（/？M）