4-(3-羟基丙基氨甲酰基)苯基硼酸 | 913835-29-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(3-羟基丙基氨甲酰基)苯基硼酸
• 中文别名: (3-羟基丙基)4-硼苯甲酰胺；4-(3-羟基丙基氨甲酰基)苯硼酸
• 英文名称: (4-((3-hydroxypropyl)carbamoyl)phenyl)boronic acid
• 英文别名: [4-(3-hydroxypropylcarbamoyl)phenyl]boronic acid
• CAS: 913835-29-7
• 化学式: C₁₀H₁₄BNO₄
• mdl: MFCD08235076
• 分子量: 223.036
• InChiKey: VDMQHVJGIAQUHA-UHFFFAOYSA-N

物化性质

• 熔点：
  224-226

计算性质

• 辛醇/水分配系数(LogP)：
  -0.15
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  89.8
• 氢给体数：
  4
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-(3-羟基丙基氨甲酰基)苯基硼酸 、 6-bromo-4-N-[3-(dimethylamino)propyl]-2-N-methylthieno[3,2-d]pyrimidine-2,4-diamine 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25%的产率得到4-[4-[3-(dimethylamino)propylamino]-2-(methylamino)thieno[3,2-d]pyrimidin-6-yl]-N-(3-hydroxypropyl)benzamide
  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

• Structure–Activity Relationship Studies of Orally Active Antimalarial 3,5-Substituted 2-Aminopyridines
  作者：Diego González Cabrera、Frederic Douelle、Yassir Younis、Tzu-Shean Feng、Claire Le Manach、Aloysius T. Nchinda、Leslie J. Street、Christian Scheurer、Jolanda Kamber、Karen L. White、Oliver D. Montagnat、Eileen Ryan、Kasiram Katneni、K. Mohammed Zabiulla、Jayan T. Joseph、Sridevi Bashyam、David Waterson、Michael J. Witty、Susan A. Charman、Sergio Wittlin、Kelly Chibale

  DOI：10.1021/jm301476b

  日期：2012.12.27

  In an effort to address potential cardiotoxicity liabilities identified with earlier frontrunner compounds, a number of new 3,5-diaryl-2-aminopyridine derivatives were synthesized. Several compounds exhibited potent antiplasmodial activity against both the multidrug resistant (K1) and sensitive (NF54) strains in the low nanomolar range. Some compounds displayed a significant reduction in potency in

  为了解决由早期先驱化合物鉴定出的潜在心脏毒性问题，合成了许多新的3,5-二芳基-2-氨基吡啶衍生物。几种化合物对低纳摩尔范围内的耐多药（K1）和敏感（NF54）菌株均显示出有效的抗疟原虫活性。与先前报道的领先者类似物相比，某些化合物在hERG通道抑制试验中显示出显着的效力降低。这些新类似物中的几种在伯氏疟原虫小鼠模型中显示出有希望的体内功效，并将进一步评估为潜在的临床候选药物。描绘了体外抗血浆和hERG活性的SAR。
• 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.