5-bromo-N-phenyl-1H-indole-1-carboxamide | 1245708-12-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-bromo-N-phenyl-1H-indole-1-carboxamide
• 英文别名: 5-bromo-N-phenylindole-1-carboxamide
• CAS: 1245708-12-6
• 化学式: C₁₅H₁₁BrN₂O
• 分子量: 315.169
• InChiKey: CNUFLYAGZLYCNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  methyl 2-((1r,4r)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclohexyl)acetate 、 5-bromo-N-phenyl-1H-indole-1-carboxamide 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium carbonate 作用下， 以 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 10.0h， 以61%的产率得到methyl 2-((1r,4r)-4-(4-(1-(phenylcarbamoyl)-1H-indol-5-yl)phenyl)cyclohexyl)acetate
  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：

  5-溴吲哚 、 苯甲酰基叠氮化物 在 copper(l) iodide 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 以67%的产率得到5-bromo-N-phenyl-1H-indole-1-carboxamide
  参考文献：
  名称：

  Cu催化酰叠氮与仲胺反应合成不对称脲衍生物

  摘要：

  不对称尿素的合成一般需要有毒试剂、溶剂和苛刻的反应条件。在此，我们介绍了在乙酸乙酯中铜催化的更环保、更安全的不对称脲衍生物合成。这种方法最大限度地减少了有毒试剂的使用。多种吲哚、胺和叠氮化物与双吲哚的成功使用导致分离尿素的高产率和克级合成。

  DOI：

  10.1002/cbdv.202200346

文献信息

• 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：Schering Corporation

  公开号：EP2408744A1

  公开（公告）日：2012-01-25
• [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：WO2010107768A1

  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 (I).
• Development of Novel Benzomorpholine Class of Diacylglycerol Acyltransferase I Inhibitors
  作者：Gang Zhou、Nicolas Zorn、Pauline Ting、Robert Aslanian、Mingxiang Lin、John Cook、Jean Lachowicz、Albert Lin、Michelle Smith、Joyce Hwa、Margaret van Heek、Scott Walker

  DOI：10.1021/ml400527n

  日期：2014.5.8

  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.
• Synthesis of Unsymmetrical Urea Derivatives via Cu‐Catalyzed Reaction of Acylazide and Secondary Amine
  作者：Jivan Shinde、Prakash Bhimrao Patil、Veerababurao Kavala、Ching‐Fa Yao

  DOI：10.1002/cbdv.202200346

  日期：2022.8

  The synthesis of unsymmetrical urea generally requires toxic reagent, solvent and harsh reaction condition. Herein, we introduce Cu-catalyzed greener and safer unsymmetrical urea derivatives synthesis in ethyl acetate. This method minimized utilization of toxic reagent. A variety of indole, amines, and azides with bis-indole successfully employed leading to high yields and gram scale synthesis of isolated

  不对称尿素的合成一般需要有毒试剂、溶剂和苛刻的反应条件。在此，我们介绍了在乙酸乙酯中铜催化的更环保、更安全的不对称脲衍生物合成。这种方法最大限度地减少了有毒试剂的使用。多种吲哚、胺和叠氮化物与双吲哚的成功使用导致分离尿素的高产率和克级合成。