(R)-7-bromo-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one | 1245708-20-6

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: (R)-7-bromo-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one
• 英文别名: (2R)-7-bromo-2-methyl-2,4-dihydro-1,4-benzoxazin-3-one；(2R)-7-bromo-2-methyl-4H-1,4-benzoxazin-3-one
• CAS: 1245708-20-6
• 化学式: C₉H₈BrNO₂
• 分子量: 242.072
• InChiKey: QVEHEXXQFGINCG-RXMQYKEDSA-N

物化性质

• 沸点：
  374.8±42.0 °C(predicted)
• 密度：
  1.551±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-7-bromo-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-7-bromo-2-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine
  参考文献：
  名称：

  Development of Novel Benzomorpholine Class of Diacylglycerol Acyltransferase I Inhibitors

  摘要：

  Diacylglycerol acyltransferase 1 (DGAT1) presents itself as a potential therapeutic target for obesity and diabetes for its important role in triglyceride biosynthesis. Herein we report the rational design of a novel class of DGAT1 inhibitors featuring a benzomorpholine core (23n). SAR exploration yielded compounds with good potency and selectivity as well as reasonable physical and pharmacokinetic properties. This class of DGAT1 inhibitors was tested in rodent models to evaluate DGAT1 inhibition as a novel approach for the treatment of metabolic diseases. Compound 23n conferred weight loss and a reduction in liver triglycerides when dosed chronically in mice with diet-induced obesity and depleted serum triglycerides following a lipid challenge.

  DOI：

  10.1021/ml400527n
• 作为产物：
  描述：

  2-硝基-5-溴苯酚 在 偶氮二甲酸二异丙酯 、 铁粉 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三苯基膦 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-7-bromo-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one
  参考文献：
  名称：

  Development of Novel Benzomorpholine Class of Diacylglycerol Acyltransferase I Inhibitors

  摘要：

  Diacylglycerol acyltransferase 1 (DGAT1) presents itself as a potential therapeutic target for obesity and diabetes for its important role in triglyceride biosynthesis. Herein we report the rational design of a novel class of DGAT1 inhibitors featuring a benzomorpholine core (23n). SAR exploration yielded compounds with good potency and selectivity as well as reasonable physical and pharmacokinetic properties. This class of DGAT1 inhibitors was tested in rodent models to evaluate DGAT1 inhibition as a novel approach for the treatment of metabolic diseases. Compound 23n conferred weight loss and a reduction in liver triglycerides when dosed chronically in mice with diet-induced obesity and depleted serum triglycerides following a lipid challenge.

  DOI：

  10.1021/ml400527n

文献信息

• [EN] BICYCLIC COMPOUNDS AS INHIBITORS OF DIACYLGLYCEROL ACYLTRANSFERASE<br/>[FR] COMPOSÉS BICYCLIQUES EN TANT QU'INHIBITEURS DE LA DIACYLGLYCÉROL ACYLTRANSFÉRASE
  申请人：SCHERING CORP

  公开号：WO2010107765A1

  公开（公告）日：2010-09-23

  The present invention relates to novel heterocyclic compounds as diacylglycerol acyltransferase ("DGAT") inhibitors, pharmaceutical compositions comprising the heterocyclic compounds and the use of the compounds for treating or preventing a cardiovascular disease, a metabolic disorder, obesity or an obesity-related disorder, diabetes, dyslipidemia, a diabetic complication, impaired glucose tolerance or impaired fasting glucose. An illustrative compound of the invention is shown below : formula (I).

  本发明涉及一种新型杂环化合物，作为二酰基甘油脂酰基转移酶（“DGAT”）抑制剂，包括所述杂环化合物的药物组合物以及利用这些化合物治疗或预防心血管疾病、代谢紊乱、肥胖或与肥胖相关的疾病、糖尿病、血脂异常、糖尿病并发症、糖耐量受损或空腹血糖受损。本发明的一个示例化合物如下所示：式（I）。
• BICYCLIC COMPOUNDS AS INHIBITORS OF DIACYLGLYCEROL ACYLTRANSFERASE
  申请人：Zhou Gang

  公开号：US20110319403A1

  公开（公告）日：2011-12-29

  The present invention relates to novel heterocyclic compounds as diacylglycerol acyltransferase (“DGAT”) inhibitors, pharmaceutical compositions comprising the heterocyclic compounds and the use of the compounds for treating or preventing a cardiovascular disease, a metabolic disorder, obesity or an obesity-related disorder, diabetes, dyslipidemia, a diabetic complication, impaired glucose tolerance or impaired fasting glucose. An illustrative compound of the invention is shown below: formula (I).

  本发明涉及一种新型杂环化合物，作为二酰基甘油酰基转移酶（“DGAT”）抑制剂，制备包含该杂环化合物的制药组合物，并用于治疗或预防心血管疾病、代谢紊乱、肥胖或肥胖相关疾病、糖尿病、血脂异常、糖尿病并发症、糖耐量受损或空腹血糖受损。该发明的一种示例化合物如下：式（I）。
• BICYCLIC COMPOUNDS AS INHIBITORS OF DIACYGLYCEROL ACYLTRANSFERASE
  申请人：Zhou Gang

  公开号：US20120022057A1

  公开（公告）日：2012-01-26

  The present invention relates to novel heterocyclic compounds as diacylglycerol acyltransferase (“DGAT”) inhibitors, pharmaceutical compositions comprising the heterocyclic compounds and the use of the compounds for treating or preventing a cardiovascular disease, a metabolic disorder, obesity or an obesity-related disorder, diabetes, dyslipidemia, a diabetic complication, impaired glucose tolerance or impaired fasting glucose. An illustrative compound of the invention is shown below (I).

  本发明涉及一种新型杂环化合物，作为二酰基甘油酰基转移酶（“DGAT”）抑制剂，包括该杂环化合物的制药组合物，并且该化合物可用于治疗或预防心血管疾病、代谢紊乱、肥胖或肥胖相关疾病、糖尿病、血脂异常、糖尿病并发症、糖耐量受损或空腹血糖受损。本发明的一种示例化合物如下所示（I）。
• Bicyclic compounds as inhibitors of diacylglycerol acyltransferase
  申请人：Zhou Gang

  公开号：US08637507B2

  公开（公告）日：2014-01-28

  The present invention relates to novel heterocyclic compounds as diacylglycerol acyltransferase (“DGAT”) inhibitors, pharmaceutical compositions comprising the heterocyclic compounds and the use of the compounds for treating or preventing a cardiovascular disease, a metabolic disorder, obesity or an obesity-related disorder, diabetes, dyslipidemia, a diabetic complication, impaired glucose tolerance or impaired fasting glucose. An illustrative compound of the invention is shown below: formula (I).

  本发明涉及新型杂环化合物作为二酰基甘油酰基转移酶（“DGAT”）抑制剂，包含这些杂环化合物的制药组合物以及使用这些化合物治疗或预防心血管疾病、代谢紊乱、肥胖或肥胖相关疾病、糖尿病、血脂异常、糖尿病并发症、糖耐量受损或空腹血糖受损。本发明的一种说明性化合物如下所示：式（I）。
• US8637507B2
  申请人：——

  公开号：US8637507B2

  公开（公告）日：2014-01-28