5-(isopentylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one | 1214736-30-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-(isopentylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
• 英文别名: 10-(3-Methylbutylamino)-1,14,15-triazatetracyclo[7.6.1.02,7.013,16]hexadeca-2,4,6,9,11,13(16),14-heptaen-8-one
• CAS: 1214736-30-7
• 化学式: C₁₈H₁₈N₄O
• 分子量: 306.367
• InChiKey: ZYSCHAZRRGTUHD-UHFFFAOYSA-N

物化性质

• 熔点：
  144-145 °C
• 沸点：
  533.4±60.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  59.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异戊胺 、 5-chloro-6H-v-triazolo<4,5,1-de>acridin-6-one 以 N,N-二甲基乙酰胺 为溶剂， 以76%的产率得到5-(isopentylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
  参考文献：
  名称：

  Triazoloacridin-6-ones as novel inhibitors of the quinone oxidoreductases NQO1 and NQO2

  摘要：

  A range of triazoloacridin-6-ones functionalized at C5 and C8 have been synthesized and evaluated for ability to inhibit NQO1 and NQO2. The compounds were computationally docked into the active site of NQO1 and NQO2, and calculated binding affinities were compared with IC50 values for enzyme inhibition. Excellent correlation coefficients were demonstrated suggesting a predictive QSAR model for this series of structurally similar analogues. From this we have identified some of these triazoloacridin-6-ones to be the most potent NQO2 inhibitors so far reported. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.059

文献信息

• Triazoloacridin-6-ones as novel inhibitors of the quinone oxidoreductases NQO1 and NQO2
  作者：Karen A. Nolan、Matthew P. Humphries、John Barnes、Jeremy R. Doncaster、Mary C. Caraher、Nicola Tirelli、Richard A. Bryce、Roger C. Whitehead、Ian J. Stratford

  DOI：10.1016/j.bmc.2009.11.059

  日期：2010.1

  A range of triazoloacridin-6-ones functionalized at C5 and C8 have been synthesized and evaluated for ability to inhibit NQO1 and NQO2. The compounds were computationally docked into the active site of NQO1 and NQO2, and calculated binding affinities were compared with IC50 values for enzyme inhibition. Excellent correlation coefficients were demonstrated suggesting a predictive QSAR model for this series of structurally similar analogues. From this we have identified some of these triazoloacridin-6-ones to be the most potent NQO2 inhibitors so far reported. (C) 2009 Elsevier Ltd. All rights reserved.