3-氯-6-甲基-苯并[d]异噁唑 | 16302-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并异恶唑
• 中文名称: 3-氯-6-甲基-苯并[d]异噁唑
• 中文别名: 3-氯-6-甲基-苯并[D]异噁唑；3-氯-6-甲基苯并[D]异恶唑
• 英文名称: 3-Chlor-6-methyl-1,2-benzisoxazol
• 英文别名: 3-chloro-6-methyl-1,2-benzisoxazole；3-chloro-6-methyl-benzo[d]isoxazole；3-Chloro-6-methylbenzo[d]isoxazole；3-chloro-6-methyl-1,2-benzoxazole
• CAS: 16302-64-0
• 化学式: C₈H₆ClNO
• mdl: MFCD06659627
• 分子量: 167.595
• InChiKey: RUNSDQIHKJDPRK-UHFFFAOYSA-N

物化性质

• 熔点：
  26 °C
• 沸点：
  269.2±20.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为产物：
  描述：

  4-甲基水杨酸甲酯 在 羟胺 、 三乙胺 、 N,N'-羰基二咪唑 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 17.0h， 生成 3-氯-6-甲基-苯并[d]异噁唑
  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

• MASP-2 INHIBITORS AND METHODS OF USE
  申请人：Omeros Corporation

  公开号：US20210171512A1

  公开（公告）日：2021-06-10

  The present disclosure provides, inter alia, compounds with MASP-2 inhibitory activity, compositions of such compounds, and methods of making and using such compounds.

  本公开提供了具有MASP-2抑制活性的化合物，这些化合物的组合物，以及制造和使用这些化合物的方法。
• Boeshagen,H., Chemische Berichte, 1967, vol. 100, # 10, p. 3326 - 3330
  作者：Boeshagen,H.

  DOI：——

  日期：——
• [EN] MASP-2 INHIBITORS AND METHODS OF USE<br/>[FR] INHIBITEURS DE MASP-2 ET PROCÉDÉS D'UTILISATION
  申请人：OMEROS CORP

  公开号：WO2021113698A1

  公开（公告）日：2021-06-10

  The present disclosure provides, inter alia, compounds with MASP-2 inhibitory activity, compositions of such compounds, and methods of making and using such compounds.
• Benzimidazolones: A New Class of Selective Peroxisome Proliferator-Activated Receptor γ (PPARγ) Modulators
  作者：Weiguo Liu、Fiona Lau、Kun Liu、Harold B. Wood、Gaochao Zhou、Yuli Chen、Ying Li、Taro E. Akiyama、Gino Castriota、Monica Einstein、Chualin Wang、Margaret E. McCann、Thomas W. Doebber、Margaret Wu、Ching H. Chang、Lesley McNamara、Brian McKeever、Ralph T. Mosley、Joel P. Berger、Peter T. Meinke

  DOI：10.1021/jm201061j

  日期：2011.12.22

  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.