2-(2-(苯并[d][1,3]间二氧杂环戊烯-5-基)丙-2-基)-1,3,4-恶二唑 | 251958-52-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 中文名称: 2-(2-(苯并[d][1,3]间二氧杂环戊烯-5-基)丙-2-基)-1,3,4-恶二唑
• 中文别名: 2-[1-(1,3-苯并间二氧杂环戊烯-5-基)-1-甲基乙基]-1,3,4-恶二唑；2-(2-(苯并[d][1,3]二氧代l-5-基)丙烷-2-基)-1,3,4-噁二唑
• 英文名称: 2-(1-Benzo[1,3]dioxol-5-yl-1-methyl-ethyl)-[1,3,4]oxadiazole
• 英文别名: 2-(2-(Benzo[d][1,3]dioxol-5-yl)propan-2-yl)-1,3,4-oxadiazole；2-[2-(1,3-benzodioxol-5-yl)propan-2-yl]-1,3,4-oxadiazole
• CAS: 251958-52-8
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: MWQXVISLSIGMCT-UHFFFAOYSA-N

物化性质

• 密度：
  1.268

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-(苯并[d][1,3]间二氧杂环戊烯-5-基)丙-2-基)-1,3,4-恶二唑 在 盐酸 、 正丁基锂 、 magnesium bromide 作用下， 以 1,4-二氧六环 、 正己烷 为溶剂， 反应 3.0h， 生成 (S)-2-Amino-1-[5-(1-benzo[1,3]dioxol-5-yl-1-methyl-ethyl)-[1,3,4]oxadiazol-2-yl]-3-methyl-butan-1-ol; hydrochloride
  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 2-(1,3-benzodioxol-5-yl)-2-methyl propanoate 在 一水合肼 作用下， 反应 16.5h， 生成 2-(2-(苯并[d][1,3]间二氧杂环戊烯-5-基)丙-2-基)-1,3,4-恶二唑
  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。
• 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）。
• 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