2-bromo-4-methyl-thiazole-5-carboxylic acid benzylamide | 959709-11-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-bromo-4-methyl-thiazole-5-carboxylic acid benzylamide
• 英文别名: N-benzyl-2-bromo-4-methylthiazole-5-carboxamide；N-benzyl-2-bromo-4-methyl-1,3-thiazole-5-carboxamide
• CAS: 959709-11-6
• 化学式: C₁₂H₁₁BrN₂OS
• 分子量: 311.202
• InChiKey: IQTQSDXJUJUFNT-UHFFFAOYSA-N

物化性质

• 沸点：
  468.5±40.0 °C(Predicted)
• 密度：
  1.513±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-4-methyl-thiazole-5-carboxylic acid benzylamide 在 copper(l) iodide 、 双三苯基磷二氯化钯 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 生成 N-苄基-2-乙炔基-4-甲基噻唑-5-甲酰胺
  参考文献：
  名称：

  Systematic evaluation of amide bioisosteres leading to the discovery of novel and potent thiazolylimidazolidinone inhibitors of SCD1 for the treatment of metabolic diseases

  摘要：

  Several five- and six-membered heterocycles were introduced to replace the C2-position amide bond of the original 2-aminothiazole-based hit compound 5. Specifically, replacement of the amide bond with an imidazolidinone moiety yielded a novel and potent thiazolylimidazolidinone series of SCD1 inhibitors. XEN723 (compound 22) was identified after optimization of the thiazolylimidazolidinone series. This compound demonstrated a 560-fold improvement in in vitro potency and reduced plasma desaturation indices in a dose dependent manner, with an EC50 of 4.5 mg/kg. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.036
• 作为产物：
  描述：

  2-溴-4-甲基噻唑-5-羧酸 、 苄胺 以the title compound was obtained as a yellow solid in 60% yield的产率得到2-bromo-4-methyl-thiazole-5-carboxylic acid benzylamide
  参考文献：
  名称：

  ORGANIC COMPOUNDS

  摘要：

  本发明提供了调节硬脂酰辅酶A去饱和酶活性的杂环衍生物。本发明还涵盖使用这种衍生物来调节硬脂酰辅酶A去饱和酶活性的方法和包含这种衍生物的制药组合物。

  公开号：

  US20100029718A1
• 作为试剂：
  描述：

  4-苄氧基-2(1H)-吡啶酮 、 ethyl 5-bromo-3-methylthiophene-2-carboxylate 在 2-bromo-4-methyl-thiazole-5-carboxylic acid benzylamide 作用下， 以the title compound was obtained as a colorless solid in 26% yield的产率得到ethyl 5-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-3-methylthiophene-2-carboxylate
  参考文献：
  名称：

  Organic compounds

  摘要：

  本发明提供了可以调节硬脂酰辅酶A去饱和酶活性的杂环衍生物。本发明还包括使用这些衍生物来调节硬脂酰辅酶A去饱和酶活性的方法和包含这些衍生物的药物组合物。

  公开号：

  US08501746B2

文献信息

• METHOD FOR ASSAYING COMPOUNDS OR AGENTS FOR ABILITY TO DISPLACE POTENT LIGANDS OF HEMATOPOIETIC PROSTAGLANDIN D SYNTHASE
  申请人：Maxey Kirk W.

  公开号：US20090286261A1

  公开（公告）日：2009-11-19

  An exemplary embodiment may be directed to a fluorescence polarization assay that screens compounds or agents for their affinity to hematopoietic prostaglandin D synthase (H-PGDS) based on their ability to displace a fluorophore-containing detection analyte bound to an enzyme comprising the primary amino acid sequence of H-PGDS. Another exemplary embodiment utilizes an enzyme having a maltose binding protein amino-acid sequence fused with an N-terminus of the enzyme.

  一个示范性实施例可能涉及一种荧光极化测定法，该方法通过检测化合物或试剂对血液造血素D合成酶（H-PGDS）的亲和力来筛选，其基于它们能够将结合到具有H-PGDS主要氨基酸序列的酶上的含荧光团的检测分析物位移开。另一个示范性实施例利用具有麦芽糖结合蛋白氨基酸序列的酶，与酶的N-末端融合。
• Heterocyclic compounds suitable for the treatment of diseases related to elevated lipid levels
  申请人：Novartis AG

  公开号：US08063084B2

  公开（公告）日：2011-11-22

  The present invention provides heterocyclic derivatives that modulate the activity of stearoyl-CoA desaturase. Methods of using such derivatives to modulate the activity of stearoyl-CoA desaturase and pharmaceutical compositions comprising such derivatives are also encompassed.

  本发明提供了杂环衍生物，可以调节硬脂酰辅酶A去饱和酶的活性。还涵盖了使用这种衍生物来调节硬脂酰辅酶A去饱和酶的活性的方法，以及包含这种衍生物的制药组合物。
• Pyrazole derivative as SCD1 inhibitors for the treatment of diabetes
  申请人：Novartis AG

  公开号：US08314138B2

  公开（公告）日：2012-11-20

  The present invention provides heterocyclic derivatives of formula I that modulate the activity of stearoyl-CoA desaturase. Methods of using such derivatives to modulate the activity of stearoyl-CoA desaturase and pharmaceutical compositions comprising such derivatives are also encompassed. wherein Q is

  本发明提供了式I的杂环衍生物，其调节硬脂酰辅酶A脱饱和酶的活性。还包括使用这些衍生物来调节硬脂酰辅酶A脱饱和酶的活性的方法以及包含这些衍生物的制药组合物。 其中Q为：（翻译不出来，需要上下文信息）
• Heterocyclic inhibitors of stearoyl-CoA desaturase
  申请人：Novartis AG

  公开号：US08236835B2

  公开（公告）日：2012-08-07

  The present invention provides heterocyclic derivatives that modulate the activity of stearoyl-CoA desaturase. Methods of using such derivatives to modulate the activity of stearoyl-CoA desaturase and pharmaceutical compositions comprising such derivatives are also encompassed.

  本发明提供了能够调节硬脂酰辅酶A去饱和酶活性的杂环衍生物。该发明还涵盖了使用这些衍生物来调节硬脂酰辅酶A去饱和酶活性的方法，以及包含这些衍生物的药物组合物。
• SCD1 inhibitors triazole and tetrazole compounds
  申请人：Novartis AG

  公开号：US08258160B2

  公开（公告）日：2012-09-04

  The present invention provides heterocyclic derivatives that modulate the activity of stearoyl-CoA desaturase. Methods of using such derivatives to modulate the activity of stearoyl-CoA desaturase and pharmaceutical compositions comprising such derivatives are also encompassed.

  本发明提供了调节硬脂酰辅酶A去饱和酶活性的杂环衍生物。还涵盖了使用这些衍生物来调节硬脂酰辅酶A去饱和酶活性的方法以及包含这些衍生物的药物组合物。