4-异丁氧基苯硼酸频哪醇酯 | 1421597-99-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-异丁氧基苯硼酸频哪醇酯
• 英文名称: 2-(4-Isobutoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 4,4,5,5-tetramethyl-2-[4-(2-methylpropoxy)phenyl]-1,3,2-dioxaborolane
• CAS: 1421597-99-0
• 化学式: C₁₆H₂₅BO₃
• 分子量: 276.184
• InChiKey: DRPZOIZUPAZNPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基-6-氯-4-羟基嘧啶 、 4-异丁氧基苯硼酸频哪醇酯 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以49.94%的产率得到2-amino-4-[4-(2-methylpropoxy)phenyl]-1H-pyrimidin-6-one
  参考文献：
  名称：

  Isocytosine-based inhibitors of xanthine oxidase: Design, synthesis, SAR, PK and in vivo efficacy in rat model of hyperuricemia

  摘要：

  Structure-activity relationship studies were carried out for lead generation following structure-guided design approach from an isocytosine scaffold identified earlier for xanthine oxidase inhibition. A 470-fold improvement in in vitro IC50 was obtained in the process. Five most potent compounds with nanomolar IC50 values were selected for pharmacokinetics and in vivo experiments. The best compound showed good in vivo activity when administered intraperitoneally but was not active by oral route. The results suggest that improvement in oral exposure could improve the in vivo efficacy of this series. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.029
• 作为产物：
  描述：

  1-溴-4-异丁氧基苯 、 联硼酸频那醇酯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 生成 4-异丁氧基苯硼酸频哪醇酯
  参考文献：
  名称：

  Isocytosine-based inhibitors of xanthine oxidase: Design, synthesis, SAR, PK and in vivo efficacy in rat model of hyperuricemia

  摘要：

  Structure-activity relationship studies were carried out for lead generation following structure-guided design approach from an isocytosine scaffold identified earlier for xanthine oxidase inhibition. A 470-fold improvement in in vitro IC50 was obtained in the process. Five most potent compounds with nanomolar IC50 values were selected for pharmacokinetics and in vivo experiments. The best compound showed good in vivo activity when administered intraperitoneally but was not active by oral route. The results suggest that improvement in oral exposure could improve the in vivo efficacy of this series. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.029

文献信息

• Isocytosine-based inhibitors of xanthine oxidase: Design, synthesis, SAR, PK and in vivo efficacy in rat model of hyperuricemia
  作者：Smriti Khanna、Sandeep Burudkar、Komal Bajaj、Pranay Shah、Ashish Keche、Usha Ghosh、Avani Desai、Ankita Srivastava、Asha Kulkarni-Almeida、Nitin J. Deshmukh、Amol Dixit、Manoja K. Brahma、Umakant Bahirat、Lalit Doshi、Kumar V.S. Nemmani、Prashant Tannu、Anagha Damre、Chandrika B-Rao、Rajiv Sharma、H. Sivaramakrishnan

  DOI：10.1016/j.bmcl.2012.10.029

  日期：2012.12

  Structure-activity relationship studies were carried out for lead generation following structure-guided design approach from an isocytosine scaffold identified earlier for xanthine oxidase inhibition. A 470-fold improvement in in vitro IC50 was obtained in the process. Five most potent compounds with nanomolar IC50 values were selected for pharmacokinetics and in vivo experiments. The best compound showed good in vivo activity when administered intraperitoneally but was not active by oral route. The results suggest that improvement in oral exposure could improve the in vivo efficacy of this series. (C) 2012 Elsevier Ltd. All rights reserved.