2-(1-甲基环丙基)-1,3,4-噁二唑 | 353238-51-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(1-甲基环丙基)-1,3,4-噁二唑
• 中文别名: 2-(1-甲基环丙基)-1,3,4-恶二唑
• 英文名称: 2-(1-Methylcyclopropyl)-1,3,4-oxadiazole
• CAS: 353238-51-4
• 化学式: C₆H₈N₂O
• 分子量: 124.142
• InChiKey: YWUFRMZKROSGOA-UHFFFAOYSA-N

物化性质

• 沸点：
  183℃
• 密度：
  1.181
• 闪点：
  65℃

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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-(1-甲基环丙基)-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 7.0h， 生成 {1-[((S)-1-{Hydroxy-[5-(1-methyl-cyclopropyl)-[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：

  1-甲基环丙烷-1-甲酸甲酯 在 对甲苯磺酸 、 一水合肼 作用下， 反应 28.0h， 生成 2-(1-甲基环丙基)-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

• 1,3,4-oxadiazole derivatives and process for producing the same
  申请人：——

  公开号：US20030130326A1

  公开（公告）日：2003-07-10

  A process for the preparation of compounds represented by formulae (I) and (IV): 1 (wherein symbols in the formulae are described in the description) and the novel 1,3,4-oxadiazole derivative compound represented by formula (I). According to the present invention, preparation of intermediates (compounds of formula (IV)) of 1,3,4-oxadiazole derivatives useful as pharmaceuticals (elastase inhibitors) can be prepared efficiently via novel synthesis intermediates (compounds of formula (I)).

  一种制备式(I)和式(IV)所代表化合物的方法：1（其中式中的符号在说明中描述），以及式(I)所代表的新型1,3,4-噁二唑衍生物化合物。根据本发明，可以通过新型合成中间体(式(I)化合物)高效地制备用于制药(弹性酶抑制剂)的1,3,4-噁二唑衍生物的中间体(式(IV)化合物)。
• 1,3,4-OXADIAZOLE DERIVATIVES AND PROCESS FOR PRODUCING THE SAME
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1253144A1

  公开（公告）日：2002-10-30

  A process for the preparation of compounds represented by formulae (I) and (IV): (wherein symbols in the formulae are described in the description) and the novel 1,3,4-oxadiazole derivative compound represented by formula (I). According to the present invention, preparation of intermediates (compounds of formula (IV)) of 1,3,4-oxadiazole derivatives useful as pharmaceuticals (elastase inhibitors) can be prepared efficiently via novel synthesis intermediates (compounds of formula (I)).

  一种制备式(I)和(IV)所代表化合物的工艺： (式中的符号已在描述中说明）和式（I）代表的新型 1,3,4-噁二唑衍生物化合物的制备方法。根据本发明，可通过新型合成中间体（式（I）化合物）高效制备用作药物（弹性蛋白酶抑制剂）的 1,3,4-噁二唑衍生物中间体（式（IV）化合物）。
• Development of Orally Active Nonpeptidic Inhibitors of Human Neutrophil Elastase
  作者：Kazuyuki Ohmoto、Tetsuya Yamamoto、Motohiro Okuma、Toshihide Horiuchi、Hirotoshi Imanishi、Yoshihiko Odagaki、Kazuhito Kawabata、Tomohiko Sekioka、Yasushi Hirota、Shozo Matsuoka、Hisao Nakai、Masaaki Toda、John C. Cheronis、Lyle W. Spruce、Albert Gyorkos、Maciej Wieczorek

  DOI：10.1021/jm000410y

  日期：2001.4.1

  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.