5-[4-[2-[N-(benzoxazol-2-yl)-N-methylamino]ethoxy]-benzyl]-oxazolidine-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 5-[4-[2-[N-(benzoxazol-2-yl)-N-methylamino]ethoxy]-benzyl]-oxazolidine-2,4-dione
• 英文别名: 5-<<4-<2-(2-benzoxazolylmethylamino)ethoxy>phenyl>methyl>-2,4-oxazolidinedione；5-(4-(2-(N-(benzoxazol-2-yl)-N-methylamino)-ethoxy)-benzyl)-oxazolidine-2,4-dione；5-[4-[2-[N-(benzoxazol-2-yl)-N-methylamino]ethoxy]benzyl]-oxazolidine-2,4-dione；5-[4-[2-(N-(benzoxazol-2-yl)-N-methylamino]ethoxy]benzyl]oxazolidine-2,4-dione；5-[[4-[2-[1,3-Benzoxazol-2-yl(methyl)amino]ethoxy]phenyl]methyl]-1,3-oxazolidine-2,4-dione
• 化学式: C₂₀H₁₉N₃O₅
• 分子量: 381.388
• InChiKey: KPONVTMPKZYMIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  93.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-氯苯并恶唑 在 吡啶 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 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

文献信息

• Method of inhibiting angiogenesis
  申请人：Genentech, Inc.

  公开号：US20010036955A1

  公开（公告）日：2001-11-01

  Angiogenesis is inhibited and the growth of tumors is treated by administering an effective amount of a PPAR gamma ligand/agonist, optionally with an RXR receptor ligand.

  血管生成受到抑制，肿瘤生长通过给予有效剂量的PPARγ配体/激动剂进行治疗，可选地与RXR受体配体一起使用。
• Methods and pharmaceutical compositions for inhibiting tumour cell growth
  申请人：DANA-FARBER CANCER INSTITUTE

  公开号：EP1410799A1

  公开（公告）日：2004-04-21

  Methods for inhibiting proliferation of a PPARγ-responsive hyperproliferative cell using PPARγ agonists are described. Pharmaceutical compositions as well as method for diagnosing and treating a PPARγ-responsive hyperproliferative cell are also described.

  描述了使用 PPARγ 激动剂抑制 PPARγ 反应性高增殖细胞增殖的方法。还描述了药物组合物以及诊断和治疗 PPARγ 反应性高增殖细胞的方法。
• Use of thiazolidinediones to prevent or delay onset of NIDDM
  申请人：Sankyo Company, Limited

  公开号：EP1637138A2

  公开（公告）日：2006-03-22

  A novel method of using thiazolidinedione derivatives and related antihyperglycemic agents to treat populations experiencing impaired glucose tolerance in order to prevent or delay the onset of noninsulin-dependent diabetes mellitus (NIDDM) and complications arising therefrom is disclosed.

  本发明公开了一种使用噻唑烷二酮衍生物和相关降血糖药治疗糖耐量受损人群的新方法，以预防或延缓非胰岛素依赖型糖尿病（NIDDM）及其并发症的发生。
• Use of thiazolidinediones to prevent or delay onset of niddm
  申请人：Sankyo Company, Limited

  公开号：EP1714652A2

  公开（公告）日：2006-10-25

  A novel method of using thiazolidinedione derivatives and related antihyperglycemic agents to treat populations experiencing impaired glucose tolerance in order to prevent or delay the onset of noninsulin-dependent diabetes mellitus (NIDDM) and complications arising therefrom is disclosed.

  本发明公开了一种使用噻唑烷二酮衍生物和相关降血糖药治疗糖耐量受损人群的新方法，以预防或延缓非胰岛素依赖型糖尿病（NIDDM）及其并发症的发生。
• METHODS AND PHARMACEUTICAL COMPOSITIONS FOR INHIBITING TUMOR CELL GROWTH
  申请人：Dana-Farber Cancer Institute

  公开号：US20020006950A1

  公开（公告）日：2002-01-17

  The present invention is based on the finding that activation of PPAR&ggr; plays a key role in inducing growth arrest and differentiation of certain actively proliferating cells. We show that administration of PPAR&ggr; agonists, such as thiazolidinedione ligands (TZDs), is effective both in vitro and in vivo at inhibiting the proiferation of such cells.

  本发明的基础是发现 PPAR&ggr; 的激活在诱导某些活跃增殖细胞的生长停滞和分化方面起着关键作用。我们的研究表明，服用 PPAR&ggr; 激动剂，如噻唑烷二酮配体（TZDs），在体外和体内都能有效抑制这类细胞的增殖。