tetrazolo[1,5-a]pyridin-6-ylboronic acid | 1588769-37-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: tetrazolo[1,5-a]pyridin-6-ylboronic acid
• CAS: 1588769-37-2
• 化学式: C₅H₅BN₄O₂
• 分子量: 163.931
• InChiKey: STCRSUWSFOPSET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(6-bromo-4-isopropyl-5-oxo-4,5-dihydrothiazolo[5,4-b]pyridin-2-yl)-3-ethylurea 、 tetrazolo[1,5-a]pyridin-6-ylboronic acid 在 碳酸氢钠 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 生成 1-ethyl-3-(4-isopropyl-5-oxo-6-(tetrazolo[1,5-a]pyridin-6-yl)-4,5-dihydrothiazolo[5,4-b]pyridin-2-yl)urea
  参考文献：
  名称：

  Thiazolopyridone ureas as DNA gyrase B inhibitors: Optimization of antitubercular activity and efficacy

  摘要：

  Scaffold hopping from the thiazolopyridine ureas led to thiazolopyridone ureas with potent antitubercular activity acting through inhibition of DNA GyrB ATPase activity. Structural diversity was introduced, by extension of substituents from the thiazolopyridone N-4 position, to access hydrophobic interactions in the ribose pocket of the ATP binding region of GyrB. Further optimization of hydrogen bond interactions with arginines in site-2 of GyrB active site pocket led to potent inhibition of the enzyme (IC50 2 nM) along with potent cellular activity (MIC = 0.1 mu M) against Mycobacterium tuberculosis (Mtb). Efficacy was demonstrated in an acute mouse model of tuberculosis on oral administration. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.080