3-Methyl-1-phenyl-4-phenylamino-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid | 183546-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-Methyl-1-phenyl-4-phenylamino-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid
• CAS: 183546-48-7
• 化学式: C₂₀H₁₆N₄O₂
• 分子量: 344.373
• InChiKey: SIGCPBRUDPGFSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  80.04
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-Methyl-1-phenyl-4-phenylamino-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid 在 三氯氧磷 作用下， 反应 3.0h， 以60%的产率得到2-Chloro-12-methyl-14-phenyl-9,13,14,16-tetrazatetracyclo[8.7.0.03,8.011,15]heptadeca-1,3,5,7,9,11(15),12,16-octaene
  参考文献：
  名称：

  SAR of a series of anti-HSV-1 acridone derivatives, and a rational acridone-based design of a new anti-HSV-1 3H-benzo[b]pyrazolo[3,4-h]-1,6-naphthyridine series

  摘要：

  Herpes Simplex Virus (HSV) infections are among the most common human diseases. In this work, we assess the structural features and electronic properties of a series of ten 1-hydroxyacridone derivatives (1a-j) recently described as a new class of non-nucleoside inhibitors of Herpes Simplex Virus-1 (HSV-1). Based on these molecules, we applied rigid analogue and isosteric replacement approaches to design and synthesize nine new 3H-benzo[b]pyrazolo[3,4-h]-1,6-naphthyridine derivatives (2a-i). The biological and computational results of these new molecules were compared with 1-hydroxyacridones. An inhibitory profile was observed in 10-Cl substituted 3H-benzo[b]pyrazolo[3,4-h]-1,6-naphthyridine derivative (2f), which presents the same substituent at the analogous position of 1-hydroxyacridone derivative (1b). The structure-activity relationship (SAR) studies pointed out the 10-position next to nitrogen atom as important for the anti-HSV-1 profile in the pyrazolo-naphthyridine derivatives tested, which reinforced the promising profile for further experimental investigation. The most potent acridone and pyrazolo-naphthridine derivatives were also submitted to an in silico ADMET screening in order to determine their overall drug-score, which confirmed their potential antiviral profile. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.09.032
• 作为产物：
  描述：

  4-chloro-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester 在 sodium hydroxide 、 乙醇 作用下， 反应 3.0h， 生成 3-Methyl-1-phenyl-4-phenylamino-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid
  参考文献：
  名称：

  SYNTHESIS AND BIOLOGICAL EVALUATION OF 1H-PYRAZOLO [3,4-b] PYRIDINE-5 CARBOXYLIC ACIDS AGAINST VACCINIA VIRUS

  摘要：

  DOI：

  10.1515/hc.2002.8.5.427