6-(2,1,3-benzoxadiazol-5-yl)-N4-[3-(dimethylamino)propyl]-N2-methyl-thieno[3,2-d]pyrimidine-2,4-diamine | 1547235-95-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 6-(2,1,3-benzoxadiazol-5-yl)-N4-[3-(dimethylamino)propyl]-N2-methyl-thieno[3,2-d]pyrimidine-2,4-diamine
• 英文别名: 6-(2,1,3-benzoxadiazol-5-yl)-4-N-[3-(dimethylamino)propyl]-2-N-methylthieno[3,2-d]pyrimidine-2,4-diamine
• CAS: 1547235-95-9
• 化学式: C₁₈H₂₁N₇OS
• 分子量: 383.477
• InChiKey: ZIBAHCFPPOHWMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  6-bromo-4-N-[3-(dimethylamino)propyl]-2-N-methylthieno[3,2-d]pyrimidine-2,4-diamine 、 2,1,3-苯并噁二唑-5-基-硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 14.25h， 以62%的产率得到6-(2,1,3-benzoxadiazol-5-yl)-N4-[3-(dimethylamino)propyl]-N2-methyl-thieno[3,2-d]pyrimidine-2,4-diamine
  参考文献：
  名称：

  2,4-Diaminothienopyrimidines as Orally Active Antimalarial Agents

  摘要：

  A novel series of 2,4-diaminothienopyrimidines with potential as antimalarials was identified from whole-cell high-throughput screening of a SoftFocus ion channel library. Synthesis and structure activity relationship studies identified compounds with potent antiplasmodial activity and low in vitro cytotoxicity. Several of these analogues exhibited in vivo activity in the Plasmodium berghei mouse model when administered orally. However, inhibition of the hERG potassium channel was identified as a liability for this series.

  DOI：

  10.1021/jm401760c

文献信息

• 2,4-Diaminothienopyrimidines as Orally Active Antimalarial Agents
  作者：Diego González Cabrera、Claire Le Manach、Frederic Douelle、Yassir Younis、Tzu-Shean Feng、Tanya Paquet、Aloysius T. Nchinda、Leslie J. Street、Dale Taylor、Carmen de Kock、Lubbe Wiesner、Sandra Duffy、Karen L. White、K. Mohammed Zabiulla、Yuvaraj Sambandan、Sridevi Bashyam、David Waterson、Michael J. Witty、Susan A. Charman、Vicky M. Avery、Sergio Wittlin、Kelly Chibale

  DOI：10.1021/jm401760c

  日期：2014.2.13

  A novel series of 2,4-diaminothienopyrimidines with potential as antimalarials was identified from whole-cell high-throughput screening of a SoftFocus ion channel library. Synthesis and structure activity relationship studies identified compounds with potent antiplasmodial activity and low in vitro cytotoxicity. Several of these analogues exhibited in vivo activity in the Plasmodium berghei mouse model when administered orally. However, inhibition of the hERG potassium channel was identified as a liability for this series.