(5R)-5-methyl-5-(3-methylphenyl)-N-trityl-oxazolidine-2,4-dione | 877681-25-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (5R)-5-methyl-5-(3-methylphenyl)-N-trityl-oxazolidine-2,4-dione
• 英文别名: (R)-5-bromomethyl-5-(3-methylphenyl)-N-trityloxazolidinedione；(R)-5-methyl-5-(3-methylphenyl)-N-trityloxazolidinedione；(5R)-5-methyl-5-(3-methylphenyl)-3-trityl-1,3-oxazolidine-2,4-dione
• CAS: 877681-25-9
• 化学式: C₃₀H₂₅NO₃
• 分子量: 447.533
• InChiKey: PNBOBXBNYPJNNG-GDLZYMKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R)-5-methyl-5-(3-methylphenyl)-N-trityl-oxazolidine-2,4-dione 在 偶氮二异丁腈 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 生成 (5R)-5-(3-bromomethylphenyl)-5-methyl-N-trityl-oxazolidine-2,4-dione
  参考文献：
  名称：

  [EN] BENZOUREAS HAVING ANTI-DIABETIC ACTIVITY
  [FR] BENZO-UREES A ACTIVITE ANTIDIABETIQUE

  摘要：

  公开号：

  WO2006022954A3
• 作为产物：
  描述：

  (2R)-2-hydroxy-2-(3-methylphenyl)propanoic acid methyl ester 在 sodium ethanolate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (5R)-5-methyl-5-(3-methylphenyl)-N-trityl-oxazolidine-2,4-dione
  参考文献：
  名称：

  Benzimidazolones: A New Class of Selective Peroxisome Proliferator-Activated Receptor γ (PPARγ) Modulators

  摘要：

  A series of benzimidazolone carboxylic acids and oxazolidinediones were designed and synthesized in search of selective PPAR gamma modulators (SPPAR gamma Ms) as potential therapeutic agents for the treatment of type II diabetes mellitus (T2DM) with improved safety profiles relative to rosiglitazone and pioglitazone, the currently marketed PPAR gamma full agonist drugs. Structure activity relationships of these potent and highly selective SPPAR gamma Ms were studied with a focus on their unique profiles as partial agonists or modulators. A variety of methods, such as X-ray aystallographic analysis, PPAR gamma transactivation coactivator profiling, gene expression profiling, and mutagenesis studies, were employed to reveal the differential interactions of these new analogues with PPAR gamma receptor in comparison to full agonists. In rodent models of T2DM, benzimidazolone analogues such as (5R)-5-(3-{[3-(5-methoxybenzisoxazol-3-yl)benzimidazol-1-yl]methyl}phenyl)-5-methyloxazolidinedione (Si) demonstrated efficacy equivalent to that of rosiglitazone. Side effects, such as fluid retention and heart weight gain associated with PPAR gamma full agonists, were diminished with 51 in comparison to rosiglitazone based on studies in two independent animal models.

  DOI：

  10.1021/jm201061j

文献信息

• Benzoureas Having Anti-Diabetic Activity
  申请人：Lui Weiguo

  公开号：US20080076810A1

  公开（公告）日：2008-03-27

  Benzourea compounds of Formula I having aryl-(CH 2 ) x -oxazolidinedione or aryl-(CH 2 ) x -thiazolidinedione substituents on one of the N atoms of the benzourea ring, wherein x is 0 or 1, are PPAR gamma agonists or partial agonists and are useful in the treatment and control of type II diabetes, including hyperglycemia and other symptoms such as dyslipidemia, hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, and obesity, that are often associated with type 2 diabetes.

  具有在苯甲酰脲环的一个N原子上具有芳基-(CH2)x-噁唑啉二酮或芳基-( )x-噻唑啉二酮取代基的公式I的苯甲酰脲化合物，其中x为0或1，是PPAR gamma激动剂或部分激动剂，并且在治疗和控制II型糖尿病，包括高血糖和其他症状，如血脂异常、高脂血症、高胆固醇血症、高三酰甘油血症和肥胖症方面非常有用，这些症状通常与2型糖尿病相关。
• [EN] INDOLES HAVING ANTI-DIABETIC ACTIVITY<br/>[FR] INDOLES A ACTIVITE ANTIDIABETIQUE
  申请人：MERCK & CO INC

  公开号：WO2006014262A3

  公开（公告）日：2006-08-03
• BENZOUREAS HAVING ANTI-DIABETIC ACTIVITY
  申请人：Merck & Co., Inc.

  公开号：EP1753423A2

  公开（公告）日：2007-02-21