4-[[4-(2-phenylethoxy)phenyl]methyl]-3H-1,2,3,5-oxathiadiazole 2-oxide | 128104-41-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[[4-(2-phenylethoxy)phenyl]methyl]-3H-1,2,3,5-oxathiadiazole 2-oxide
• 英文别名: 4-[[4-(2-phenylethoxy)phenyl]methyl]-5H-1,2,3,5-oxathiadiazole 2-oxide
• CAS: 128104-41-6
• 化学式: C₁₆H₁₆N₂O₃S
• 分子量: 316.381
• InChiKey: ZDCJUSDAYUFHBA-UHFFFAOYSA-N

物化性质

• 熔点：
  96-97 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  500.8±60.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  96.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  <4-(2-phenylethoxy)phenyl>acetonitrile 在 吡啶 、 氯化亚砜 、 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.33h， 生成 4-[[4-(2-phenylethoxy)phenyl]methyl]-3H-1,2,3,5-oxathiadiazole 2-oxide
  参考文献：
  名称：

  Antihyperglycemic activity of novel substituted 3H-1,2,3,5-oxathiadiazole 2-oxides

  摘要：

  A series of substituted 3H-1,2,3,5-oxathiadiazole-2-oxides (6) was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. The oxathiadiazoles 6 were synthesized by a two-step sequence: treatment of a substituted acetonitrile (4) with hydroxylamine to give the corresponding amidoxime (5) and cyclization with thionyl chloride to yield 6. In terms of potency, the 2-naphthalenylmethyl group (as in compound 3) was found to be the optimal substituent in this series. Compound 3 was approximately 5 times more potent than ciglitazone (1).

  DOI：

  10.1021/jm00085a002

文献信息

• Novel benzyl-3H-1,2,3,5-oxathiadiazole 2-oxides useful as
  申请人：American Home Products Corp.

  公开号：US04895862A1

  公开（公告）日：1990-01-23

  This invention relates to novel benzyl-3H-1,2,3,5-oxathiadiazole 2-oxides, to the processes for their preparation, to methods for using the compounds, and to pharmaceutical preparations thereof. The compounds have pharmaceutical properties which render them beneficial for the treatment of diabetes mellitus and associated conditions.

  该发明涉及新型苄基-3H-1,2,3,5-噻二唑二氧化物，以及其制备方法、化合物的使用方法和药物制剂。这些化合物具有药理特性，可用于治疗糖尿病及相关病症。
• ALESSI, THOMAS R.;DOLAK, TERENCE M.
  作者：ALESSI, THOMAS R.、DOLAK, TERENCE M.

  DOI：——

  日期：——
• US4895862A
  申请人：——

  公开号：US4895862A

  公开（公告）日：1990-01-23
• Antihyperglycemic activity of novel substituted 3H-1,2,3,5-oxathiadiazole 2-oxides
  作者：John W. Ellingboe、Thomas R. Alessi、Terence M. Dolak、Thomas T. Nguyen、John D. Tomer、Frieda Guzzo、Jehan F. Bagli、Michael L. McCaleb

  DOI：10.1021/jm00085a002

  日期：1992.4

  A series of substituted 3H-1,2,3,5-oxathiadiazole-2-oxides (6) was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. The oxathiadiazoles 6 were synthesized by a two-step sequence: treatment of a substituted acetonitrile (4) with hydroxylamine to give the corresponding amidoxime (5) and cyclization with thionyl chloride to yield 6. In terms of potency, the 2-naphthalenylmethyl group (as in compound 3) was found to be the optimal substituent in this series. Compound 3 was approximately 5 times more potent than ciglitazone (1).