5-([4-benzyloxyphenyl]methyl)oxazolidine-2,4-dione | 141109-84-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-([4-benzyloxyphenyl]methyl)oxazolidine-2,4-dione
• 英文别名: 5-[(4-Benzyloxy)benzyl]oxazolidine-2,4-dione；5-[(4-phenylmethoxyphenyl)methyl]-1,3-oxazolidine-2,4-dione
• CAS: 141109-84-4
• 化学式: C₁₇H₁₅NO₄
• 分子量: 297.31
• InChiKey: FMYHVYFXJFLHCK-UHFFFAOYSA-N

物化性质

• 密度：
  1.282±0.06 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：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-([4-benzyloxyphenyl]methyl)oxazolidine-2,4-dione 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 1,4-二氧六环 为溶剂， 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：

  尿素 、 ethyl 3-(4-benzyloxyphenyl)lactate 在 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 以82%的产率得到5-([4-benzyloxyphenyl]methyl)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

• 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.

  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。
• 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
• US6288096B1
  申请人：——

  公开号：US6288096B1

  公开（公告）日：2001-09-11
• [EN] NEW THIAZOLIDINEDIONE, OXAZOLIDINEDIONE AND OXADIAZOLIDINEDIONE DERIVATIVES<br/>[FR] NOUVEAUX THIAZOLIDINEDIONES, OXAZOLIDINEDIONES ET DERIVES D'OXAZOLIDINEDIONES
  申请人：ASTRA AKTIEBOLAG

  公开号：WO1998057941A1

  公开（公告）日：1998-12-23

  (EN) 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.(FR) L'invention concerne de nouveaux thiazolidinediones, oxazolidinediones, dérivés d'oxazolidinediones ainsi que leur procédé de production, les préparations pharmaceutiques les contenant et l'utilisation de ces composés dans des états liés à la résistance insulinique.