2-(2-苯基丙烷-2-基)-1,3,4-噁二唑 | 252253-32-0

• 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-苯基丙烷-2-基)-1,3,4-噁二唑
• 中文别名: 2-(1-甲基-1-苯乙基)-1,3,4-恶二唑；2-(2-苯基丙烷-2-基)-1,3,4-恶二唑
• 英文名称: 2-(1-methyl-1-phenylethyl)-1,3,4-oxadiazole
• 英文别名: 2-(2-Phenylpropan-2-yl)-1,3,4-oxadiazole
• CAS: 252253-32-0
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: IXXIAIHMNPBWFL-UHFFFAOYSA-N

物化性质

• 沸点：
  297℃
• 密度：
  1.094
• 闪点：
  128℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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-苯基丙烷-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 {1-[((S)-1-{Hydroxy-[5-(1-methyl-1-phenyl-ethyl)-[1,3,4]oxadiazol-2-yl]-methyl}-2-methyl-propylcarbamoyl)-methyl]-6-oxo-2-phenyl-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：

  2,2-二甲基苯乙酸甲酯 在 一水合肼 作用下， 反应 16.5h， 生成 2-(2-苯基丙烷-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

文献信息

• Peptoid and nonpeptoid containing alpha-keto oxadiazoles as serine protease inhibitors
  申请人：——

  公开号：US20020010315A1

  公开（公告）日：2002-01-24

  The present invention relates to certain substituted oxadiazole peptoids and nonpeptoids useful as inhibitors of serine proteases, especially human neutophil elastase (HNE). Compounds of the present invention are useful for the treatment or amelioration of symptoms of adult respiratory distress syndrome, septic shock, and multiple organ failure. Processes mediated by HNE are also implicated in conditions such as arthritis, periodontal disease, glomerulonephritis, and cystic fibrosis.

  本发明涉及某些取代噁唑肽和非肽类化合物，其可用作丝氨酸蛋白酶抑制剂，特别是人类中性粒细胞弹性蛋白酶（HNE）的抑制剂。本发明化合物可用于治疗或缓解成人呼吸窘迫综合症、脓毒症休克和多器官衰竭的症状。由HNE介导的过程也与关节炎、牙周病、肾小球肾炎和囊性纤维化等疾病有关。
• EP1089752A4
  申请人：——

  公开号：EP1089752A4

  公开（公告）日：2002-01-02
• ALPHA-KETO OXADIAZOLES AS SERINE PROTEASE INHIBITORS
  申请人：Cortech Inc.

  公开号：EP1089752A1

  公开（公告）日：2001-04-11
• PEPTOID AND NONPEPTOID CONTAINING ALPHA-KETO OXADIAZOLES AS SERINE PROTEASE INHIBITORS
  申请人：Cortech Inc.

  公开号：EP1135151A1

  公开（公告）日：2001-09-26
• EP1135151A4
  申请人：——

  公开号：EP1135151A4

  公开（公告）日：2002-01-02