2-(2-间甲苯丙烷-2-基)-1,3,4-噁二唑 | 1026444-42-7

• 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: 2-(2-间甲苯丙烷-2-基)-1,3,4-噁二唑
• 中文别名: 2-[1-甲基-1-(3-甲基苯基)乙基]-1,3,4-恶二唑
• 英文名称: 2-(1-Methyl-1-m-tolyl-ethyl)-[1,3,4]oxadiazole
• 英文别名: 2-(2-m-Tolylpropan-2-yl)-1,3,4-oxadiazole；2-[2-(3-methylphenyl)propan-2-yl]-1,3,4-oxadiazole
• CAS: 1026444-42-7
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: ZJUQWUGXLMAYEK-UHFFFAOYSA-N

物化性质

• 密度：
  1.074

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-间甲苯丙烷-2-基)-1,3,4-噁二唑 在 N-甲基吗啉 、 盐酸 、 正丁基锂 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 magnesium bromide 作用下， 以 1,4-二氧六环 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 {2-(4-fluoro-phenyl)-1-[(1-{hydroxy-[5-(1-methyl-1-m-tolyl-ethyl)-[1,3,4]oxadiazol-2-yl]-methyl}-2-methyl-propylcarbamoyl)-methyl]-6-oxo-1,6-dihydro-pyrimidin-5-yl}-carbamic acid benzyl ester
  参考文献：
  名称：

  Development of Orally Active Nonpeptidic Inhibitors of Human Neutrophil Elastase

  摘要：

  5-Amino-2-phenylpyrimidin-6-ones, some of their desamino derivatives, and miscellaneous derivatives were synthesized and biologically evaluated on both in vitro activity and oral activity in an acute hemorrhagic assay. These compounds contained an alpha -keto-1,3,4-oxadiazole moiety to bind covalently to the Ser-195 hydroxy group of human neutrophil elastase (HNE). Among those tested, compounds 11a-c,e,i-1(F), 11d,e,k(H), ald,e,k(F), and ald,e(H) showed a good oral profile. RS-Mixture 3(H) was selected for clinical evaluation based on its oral potency, duration of action, enzyme selectivity, safety profile, and ease of synthesis. Structure-activity relationships (SARs) are discussed.

  DOI：

  10.1021/jm000410y
• 作为产物：
  描述：

  methyl α-(3-methylphenyl)isobutyrate 在 一水合肼 作用下， 反应 16.5h， 生成 2-(2-间甲苯丙烷-2-基)-1,3,4-噁二唑
  参考文献：
  名称：

  Development of Orally Active Nonpeptidic Inhibitors of Human Neutrophil Elastase

  摘要：

  5-Amino-2-phenylpyrimidin-6-ones, some of their desamino derivatives, and miscellaneous derivatives were synthesized and biologically evaluated on both in vitro activity and oral activity in an acute hemorrhagic assay. These compounds contained an alpha -keto-1,3,4-oxadiazole moiety to bind covalently to the Ser-195 hydroxy group of human neutrophil elastase (HNE). Among those tested, compounds 11a-c,e,i-1(F), 11d,e,k(H), ald,e,k(F), and ald,e(H) showed a good oral profile. RS-Mixture 3(H) was selected for clinical evaluation based on its oral potency, duration of action, enzyme selectivity, safety profile, and ease of synthesis. Structure-activity relationships (SARs) are discussed.

  DOI：

  10.1021/jm000410y