2-(3,4-dimethoxyphenyl)-5-methyl-1,3-benzoxazole | 876712-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3,4-dimethoxyphenyl)-5-methyl-1,3-benzoxazole
• CAS: 876712-84-4
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: DTKPVIWYVFLICC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  44.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethoxyphenyl)-5-methyl-1,3-benzoxazole 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 3.5h， 以75%的产率得到5-(bromomethyl)-2-(3,4-dimethoxyphenyl)-1,3-benzoxazole
  参考文献：
  名称：

  Design, synthesis and evaluation of 2-aryl benzoxazoles as promising hit for the A_2Areceptor

  摘要：

  The development of adenosine A_2A receptor antagonists has received much interest in recent years for the treatment of neurodegenerative diseases. Based on docking studies, a new series of 2-arylbenzoxazoles has been identified as potential A_2AR antagonists. Structure-affinity relationship was investigated in position 2, 5 and 6 of the benzoxazole heterocycle leading to compounds with a micromolar affinity towards the A_2A receptor. Compound F1, with an affinity of 1 μm, presented good absorption, distribution, metabolism and excretion properties with an excellent aqueous solubility (184 μm) without being cytotoxic at 100 μm. This compound, along with low-molecular weight compound D1 (K_i = 10 μm), can be easily modulated and thus considered as relevant starting points for further hit-to-lead optimisation.

  DOI：

  10.1080/14756366.2017.1334648
• 作为产物：
  描述：

  N-(2-hydroxy-5-methylphenyl)-3,4-dimethoxybenzamide 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 17.0h， 以80%的产率得到2-(3,4-dimethoxyphenyl)-5-methyl-1,3-benzoxazole
  参考文献：
  名称：

  Design, synthesis and evaluation of 2-aryl benzoxazoles as promising hit for the A_2Areceptor

  摘要：

  The development of adenosine A_2A receptor antagonists has received much interest in recent years for the treatment of neurodegenerative diseases. Based on docking studies, a new series of 2-arylbenzoxazoles has been identified as potential A_2AR antagonists. Structure-affinity relationship was investigated in position 2, 5 and 6 of the benzoxazole heterocycle leading to compounds with a micromolar affinity towards the A_2A receptor. Compound F1, with an affinity of 1 μm, presented good absorption, distribution, metabolism and excretion properties with an excellent aqueous solubility (184 μm) without being cytotoxic at 100 μm. This compound, along with low-molecular weight compound D1 (K_i = 10 μm), can be easily modulated and thus considered as relevant starting points for further hit-to-lead optimisation.

  DOI：

  10.1080/14756366.2017.1334648