4-(1-benzyl-1H-1,2,3-triazol-4-yl)benzene-1,2-diol | 1141892-76-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(1-benzyl-1H-1,2,3-triazol-4-yl)benzene-1,2-diol
• 英文别名: 4-(1-Benzyltriazol-4-yl)benzene-1,2-diol；4-(1-benzyltriazol-4-yl)benzene-1,2-diol
• CAS: 1141892-76-3
• 化学式: C₁₅H₁₃N₃O₂
• 分子量: 267.287
• InChiKey: YLZNTCAMAVOLAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-溴邻苯二酚 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 4-甲基苯磺酸吡啶 、 copper(II) sulfate 、 sodium ascorbate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 2.0h， 生成 4-(1-benzyl-1H-1,2,3-triazol-4-yl)benzene-1,2-diol
  参考文献：
  名称：

  1-Benzyl-4-phenyl-1H-1,2,3-triazoles improve the transcriptional functions of estrogen-related receptor γ and promote the browning of white adipose

  摘要：

  The estrogen-related receptor gamma (ERR gamma) is a potential molecular target for the development of small molecules to stimulate the adipose browning process, which may represent a novel attractive strategy to treat obesity related disorders. The receptor possesses a very small ligand binding cavity and therefore identification of small molecule ERR gamma modulators is a considerable challenge. We have successfully designed and synthesized a series of 1-benzyl-4-phenyl-1H-1,2,3-triazoles and demonstrated that they improve the transcriptional functions of ERR gamma, potently elevating both the mRNA levels and the protein levels of ERR gamma downstream targets. One of the most promising compounds, 4-(1-(4-iso-propylbenzyl)-1H-1,2,3-triazol-4-yl)benzene-1,2-diol (2e) was further shown to directly bind with the ERR gamma ligand binding domain (ERR gamma-LBD) in an isothermal calorimetric (ITC) assay and to thermally stabilize ERR gamma-LBD protein by increasing its melting temperature (T-m) as demonstrated by circular dichroism (CD) spectroscopy. Furthermore, 2e potently stimulates the adipocyte browning process and induces mitochondrial biogenesis both in vitro and in vivo, suggesting the considerable therapeutic potential of this compound for the treatment of obesity and related disorders. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.03.082

文献信息

• Synthesis and structure-function analysis of Fe(II)-form-selective antibacterial inhibitors of Escherichia coli methionine aminopeptidase
  作者：Wen-Long Wang、Sergio C. Chai、Qi-Zhuang Ye

  DOI：10.1016/j.bmcl.2009.01.011

  日期：2009.2

  Methionine aminopeptidase (MetAP) is a promising target for the development of novel antibacterial, antifungal and anticancer therapy. Based on our previous results, catechol derivatives coupled with a thiazole or thiophene moiety showed high potency and selectivity toward the Fe(II)-form of Escherichia coli MetAP, and some of them clearly showed antibacterial activity, indicating that Fe(II) is likely the physiologically relevant metal for MetAP in E. coli and other bacterial cells. To further understand the structure-function relationship of these Fe(II)-form selective MetAP inhibitors, a series of catechol derivatives was designed and synthesized by replacement of the thiazole or thiophene moiety with different five-membered and six-membered heterocycles. Inhibitory activities of these newly synthesized MetAP inhibitors indicate that many five- and six-membered rings can be accommodated by MetAP and potency on the Fe(II)-form can be improved by introducing substitutions on the heterocyles to explore additional interactions with the enzyme. The furan-containing catechols 11-13 showed the highest potency at 1 mu M on the Fe(II)-form MetAP, and they were also among the best inhibitors for growth inhibition against E. coli AS19 strain. These findings provide useful information for the design and discovery of more effective MetAP inhibitors for therapeutic applications. (C) 2009 Elsevier Ltd. All rights reserved.
• 1-Benzyl-4-phenyl-1H-1,2,3-triazoles improve the transcriptional functions of estrogen-related receptor γ and promote the browning of white adipose
  作者：Shilin Xu、Liufeng Mao、Ping Ding、Xiaoxi Zhuang、Yang Zhou、Lei Yu、Yingxue Liu、Tao Nie、Tingting Xu、Yong Xu、Jinsong Liu、Jeff Smaill、Xiaomei Ren、Donghai Wu、Ke Ding

  DOI：10.1016/j.bmc.2015.03.082

  日期：2015.7

  The estrogen-related receptor gamma (ERR gamma) is a potential molecular target for the development of small molecules to stimulate the adipose browning process, which may represent a novel attractive strategy to treat obesity related disorders. The receptor possesses a very small ligand binding cavity and therefore identification of small molecule ERR gamma modulators is a considerable challenge. We have successfully designed and synthesized a series of 1-benzyl-4-phenyl-1H-1,2,3-triazoles and demonstrated that they improve the transcriptional functions of ERR gamma, potently elevating both the mRNA levels and the protein levels of ERR gamma downstream targets. One of the most promising compounds, 4-(1-(4-iso-propylbenzyl)-1H-1,2,3-triazol-4-yl)benzene-1,2-diol (2e) was further shown to directly bind with the ERR gamma ligand binding domain (ERR gamma-LBD) in an isothermal calorimetric (ITC) assay and to thermally stabilize ERR gamma-LBD protein by increasing its melting temperature (T-m) as demonstrated by circular dichroism (CD) spectroscopy. Furthermore, 2e potently stimulates the adipocyte browning process and induces mitochondrial biogenesis both in vitro and in vivo, suggesting the considerable therapeutic potential of this compound for the treatment of obesity and related disorders. (C) 2015 Elsevier Ltd. All rights reserved.