1,3,4-triazoleboronic acid | 1219080-60-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3,4-triazoleboronic acid
• 英文别名: 1H-1,2,4-triazol-5-ylboronic acid
• CAS: 1219080-60-0
• 化学式: C₂H₄BN₃O₂
• 分子量: 112.884
• InChiKey: WVTLBJRAZJAABT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.52
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-bromo-phenyl)-5-trifluoromethyl-1H-benzoimidazole 、 1,3,4-triazoleboronic acid 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 反应 0.25h， 生成 2-[4-(1H-1,2,4-triazol-5-yl)phenyl]-6-(trifluoromethyl)-1H-benzimidazole
  参考文献：
  名称：

  Fragment-based lead discovery of a novel class of small molecule antagonists of neuropeptide B/W receptor subtype 1 (GPR7)

  摘要：

  Here, we report the discovery of a new class of NPBWR1 antagonists identified from a fragment-based screen. Compound 1 (cAMP IC₅₀ = 250 µM; LE = 0.29) emerged as an initial hit. Further optimization of 1 by SAR-by-catalogue and chemical modification produced 21a (cAMP IC₅₀ = 30 nM; LE = 0.39) with a 6700-fold increase in potency from fragment 1. Somewhat surprisingly, Schild analysis of compound 21a suggested that in vitro inhibition of NPW-mediated effects on upon cAMP accumulation were saturable, and that compound 21a dose-dependently increased [125I]-hNPW23 dissociation rate constants from NPBWR1 in kinetic binding studies. Collectively, these data are inconsistent with a classic surmountable, orthosteric mechanism of inhibition. The benzimidazole inhibitors reported herein may therefore represent a mechanistically differentiated class of compounds with which to form a better appreciation of the pharmacology and physiological roles of this central neuropeptide system.

  DOI：

  10.1016/j.bmcl.2020.127510