1-(4-bromophenyl)-4-methyl-1H-1,2,3-triazole-5-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-bromophenyl)-4-methyl-1H-1,2,3-triazole-5-carbaldehyde
• 英文别名: 3-(4-Bromophenyl)-5-methyltriazole-4-carbaldehyde；3-(4-bromophenyl)-5-methyltriazole-4-carbaldehyde
• 化学式: C₁₀H₈BrN₃O
• 分子量: 266.097
• InChiKey: BMWXNHGQAHNGAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-4-methyl-1H-1,2,3-triazole-5-carbaldehyde 在 三乙基硅烷 、 四(三苯基膦)钯 、 三溴化硼 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-((1-(4-(furan-2-yl)phenyl)-4-methyl-1H-1,2,3-triazol-5-yl)methyl)phenol
  参考文献：
  名称：

  Selective PPARδ Modulators Improve Mitochondrial Function: Potential Treatment for Duchenne Muscular Dystrophy (DMD)

  摘要：

  The X-ray structure of the previously reported PPAR delta modulator 1 bound to the ligand binding domain (LBD) revealed that the amide moiety in 1 exists in the thermodynamically disfavored cis-amide orientation. Isosteric replacement of the cis-amide with five-membered heterocycles led to the identification of imidazole 17 (MA-0204), a potent, selective PPAR delta modulator with good pharmacokinetic properties. MA-0204 was tested in vivo in mice and in vitro in patient derived muscle myoblasts (from Duchenne Muscular Dystrophy (DMD) patients); 17 altered the expression of PPAR delta target genes and improved fatty acid oxidation, which supports the therapeutic hypothesis for the study of MA-0204 in DMD patients.

  DOI：

  10.1021/acsmedchemlett.8b00287
• 作为产物：
  描述：

  1-叠氮基-4-溴苯 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 1-(4-bromophenyl)-4-methyl-1H-1,2,3-triazole-5-carbaldehyde
  参考文献：
  名称：

  Selective PPARδ Modulators Improve Mitochondrial Function: Potential Treatment for Duchenne Muscular Dystrophy (DMD)

  摘要：

  The X-ray structure of the previously reported PPAR delta modulator 1 bound to the ligand binding domain (LBD) revealed that the amide moiety in 1 exists in the thermodynamically disfavored cis-amide orientation. Isosteric replacement of the cis-amide with five-membered heterocycles led to the identification of imidazole 17 (MA-0204), a potent, selective PPAR delta modulator with good pharmacokinetic properties. MA-0204 was tested in vivo in mice and in vitro in patient derived muscle myoblasts (from Duchenne Muscular Dystrophy (DMD) patients); 17 altered the expression of PPAR delta target genes and improved fatty acid oxidation, which supports the therapeutic hypothesis for the study of MA-0204 in DMD patients.

  DOI：

  10.1021/acsmedchemlett.8b00287

文献信息

• Selective PPARδ Modulators Improve Mitochondrial Function: Potential Treatment for Duchenne Muscular Dystrophy (DMD)
  作者：Bharat Lagu、Arthur F. Kluge、Effie Tozzo、Ross Fredenburg、Eric L. Bell、Matthew M. Goddeeris、Peter Dwyer、Andrew Basinski、Ramesh S. Senaiar、Mahaboobi Jaleel、Nirbhay Kumar Tiwari、Sunil K. Panigrahi、Narasimha Rao Krishnamurthy、Taisuke Takahashi、Michael A. Patane

  DOI：10.1021/acsmedchemlett.8b00287

  日期：2018.9.13

  The X-ray structure of the previously reported PPAR delta modulator 1 bound to the ligand binding domain (LBD) revealed that the amide moiety in 1 exists in the thermodynamically disfavored cis-amide orientation. Isosteric replacement of the cis-amide with five-membered heterocycles led to the identification of imidazole 17 (MA-0204), a potent, selective PPAR delta modulator with good pharmacokinetic properties. MA-0204 was tested in vivo in mice and in vitro in patient derived muscle myoblasts (from Duchenne Muscular Dystrophy (DMD) patients); 17 altered the expression of PPAR delta target genes and improved fatty acid oxidation, which supports the therapeutic hypothesis for the study of MA-0204 in DMD patients.