5-<(4-hydroxyphenyl)methyl>-2,4-oxazolidinedione | 141109-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-<(4-hydroxyphenyl)methyl>-2,4-oxazolidinedione
• 英文别名: 5-([4-hydroxyphenyl]methyl)oxazolidine-2,4-dione；5-[(4-hydroxyphenyl)methyl]-1,3-oxazolidine-2,4-dione
• CAS: 141109-85-5
• 化学式: C₁₀H₉NO₄
• 分子量: 207.186
• InChiKey: YZOASIXXWTWEFI-UHFFFAOYSA-N

物化性质

• 密度：
  1.423±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-<(4-hydroxyphenyl)methyl>-2,4-oxazolidinedione 、 methanesulfonic acid 2-(benzooxazol-2-ylmethylamino)ethyl ester 在 sodium hydride 作用下， 生成 5-[4-[2-[N-(benzoxazol-2-yl)-N-methylamino]ethoxy]-benzyl]-oxazolidine-2,4-dione
  参考文献：
  名称：

  [[.omega.-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents

  摘要：

  A series of [(ureidoethoxy)benzyl]-2,4-thiazolidinediones and [[(heterocyclylamino)alkoxy]-benzyl]-2,4-thiazolidinediones was synthesized from the corresponding aldehydes. Compounds from the urea series, exemplified by 16, showed antihyperglycemic potency comparable with known agents of the type such as pioglitazone and troglitazone (CS-045). The benzoxazole 49, a cyclic analogue of 16, was a very potent enhancer of insulin sensitivity, and by modification of the aromatic heterocycle, an aminopyridine, 37, was identified as a lead compound from SAR studies. Evaluation of antihyperglycemic activity together with effects on blood hemoglobin content, to determine the therapeutic index, was performed in 8-day repeat administration studies in genetically obese C57 Bl/6 ob/ob mice. From these studies, BRL 49653 (37) has been selected, on the basis of antihyperglycemic potency combined with enhanced selectivity against reductions in blood hemoglobin content, for further evaluation.

  DOI：

  10.1021/jm00049a017
• 作为产物：
  描述：

  5-([4-benzyloxyphenyl]methyl)oxazolidine-2,4-dione 在 钯 作用下， 以 1,4-二氧六环 为溶剂， 以to give 1.8 g (yield 94%) of 5-([4-hydroxyphenyl]methyl)oxazolidine-2,4-dione的产率得到5-<(4-hydroxyphenyl)methyl>-2,4-oxazolidinedione
  参考文献：
  名称：

  Thiazolidinedione, oxazolidinedione and oxadiazolidinedione derivatives

  摘要：

  小说类噻唑烷，噁唑烷和噁唑二烷衍生物，其制造过程，包含它们的药物制剂以及在与胰岛素抵抗有关的疾病中使用这些化合物的用途。

  公开号：

  US06288096B1

文献信息

• Thiazolidinedione, oxazolidinedione and oxadiazolidinedione derivatives
  申请人：AstraZeneca AB

  公开号：US06288096B1

  公开（公告）日：2001-09-11

  Novel thiazolidinedione, oxazolidinedione and oxadiazolidinedione derivatives, process for their manufacture, pharmaceutical preparations containing them and the use of the compounds in conditions associated with insulin resistance.

  新型噻唑烷二酮、噁唑烷二酮和噁二唑烷二酮衍生物，其制造方法，含有它们的药物制剂以及在与胰岛素抵抗相关的病症中使用这些化合物。
• OXAZOLIDINE DIONE DERIVATIVES
  申请人：BEECHAM GROUP plc

  公开号：EP0542816A1

  公开（公告）日：1993-05-26
• 8-EN-19, 11$g(b)-ÜBERBRÜCKTE STEROIDE, DEREN HERSTELLUNG UND DIESE ENTHALTENDE PHARMAZEUTISCHE PRÄPARATE
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0559690A1

  公开（公告）日：1993-09-15
• NEW THIAZOLIDINEDIONE, OXAZOLIDINEDIONE AND OXADIAZOLIDINEDIONE DERIVATIVES
  申请人：Astra Aktiebolag

  公开号：EP0991632A1

  公开（公告）日：2000-04-12
• US5391565A
  申请人：——

  公开号：US5391565A

  公开（公告）日：1995-02-21