3-(3-Chlorobenzyl)-2,3-dihydro-1,3-benzoxazol-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 3-(3-Chlorobenzyl)-2,3-dihydro-1,3-benzoxazol-2-one
• 英文别名: 3-[(3-chlorophenyl)methyl]-1,3-benzoxazol-2-one
• 化学式: C₁₄H₁₀ClNO₂
• 分子量: 259.692
• InChiKey: RYQQWSVUVIURCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-苯并唑啉酮 、 间氯氯苄 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 3-(3-Chlorobenzyl)-2,3-dihydro-1,3-benzoxazol-2-one
  参考文献：
  名称：

  Identification of 2-benzoxazolinone derivatives as lead against molecular targets of diabetic complications

  摘要：

  AbstractDiabetic complications follow multiple pathophysiological pathways involving aldose reductase (ALR2)‐mediated polyol pathway, advanced glycation end products (AGEs) and reactive oxygen species formation. Literature suggests ALR2 inhibitors such as epalrestat to possess significant potential in retinopathy and neuropathy. Thus, in this study, multiple pathophysiology directed molecules targeting ALR2, AGEs and free radicals formation were designed using in silico techniques. Initially, database was screened via in silico tools to obtain hits with affinity for the catalytic domain of ALR2. Additional focus was laid on the presence of structural attributes responsible for AGE's inhibitory and anti‐oxidant potential. Out of obtained hits, 2‐benzoxazolinone scaffold was selected and ten derivatives were synthesized accordingly. Finally, the synthesized molecules were evaluated for their ALR2 and AGEs inhibitory activities along with free radical scavenging potency.

  DOI：

  10.1111/cbdd.13369

文献信息

• Identification of 2-benzoxazolinone derivatives as lead against molecular targets of diabetic complications
  作者：Bhawna Vyas、Shalki Choudhary、Pankaj Kumar Singh、Baldev Singh、Renu Bahadur、Ashok Kumar Malik、Om Silakari

  DOI：10.1111/cbdd.13369

  日期：2018.12

  AbstractDiabetic complications follow multiple pathophysiological pathways involving aldose reductase (ALR2)‐mediated polyol pathway, advanced glycation end products (AGEs) and reactive oxygen species formation. Literature suggests ALR2 inhibitors such as epalrestat to possess significant potential in retinopathy and neuropathy. Thus, in this study, multiple pathophysiology directed molecules targeting ALR2, AGEs and free radicals formation were designed using in silico techniques. Initially, database was screened via in silico tools to obtain hits with affinity for the catalytic domain of ALR2. Additional focus was laid on the presence of structural attributes responsible for AGE's inhibitory and anti‐oxidant potential. Out of obtained hits, 2‐benzoxazolinone scaffold was selected and ten derivatives were synthesized accordingly. Finally, the synthesized molecules were evaluated for their ALR2 and AGEs inhibitory activities along with free radical scavenging potency.