Methyl 4-[(2-naphthylsulfonyl)amino]benzoate | 327094-25-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Methyl 4-[(2-naphthylsulfonyl)amino]benzoate
• 英文别名: methyl 4-(naphthalen-2-ylsulfonylamino)benzoate
• CAS: 327094-25-7
• 化学式: C₁₈H₁₅NO₄S
• 分子量: 341.387
• InChiKey: CRDKWTKQTKMXMS-UHFFFAOYSA-N

物化性质

• 沸点：
  534.3±52.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 4-[(2-naphthylsulfonyl)amino]benzoate 在 羟胺钾盐 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以66%的产率得到N-hydroxy-4-(naphthalene-2-sulfonamido)benzamide
  参考文献：
  名称：

  Discovery of a series of small molecules as potent histone deacetylase inhibitors

  摘要：

  A series of small molecules were designed and synthesized based on our previous virtual screening approach, which was performed to discover potent histone deacetylase inhibitors (HDACIs) with novel structures. The derived compounds were tested by Hela cell nucleus extract for enzyme inhibition assay. Tumor cell growth inhibition assays were performed using a series of tumor cell lines. Molecule 4h has the best performance among these compounds with enzyme inhibition IC50 of 0.14 mu M and tumor cell growth inhibition IC50 of 1.85 (U937), 2.02 (HL60), 2.67 (K562). Docking studies showed that multiple H-bonds and hydrophobic interactions make 4h binding to the active site of HDAC. 4h has the advantage of low molecular weight, so a variety of structural modifications can be performed in our further studies.

  DOI：

  10.3109/14756366.2013.780237
• 作为产物：
  描述：

  对氨基苯甲酸 在 碳酸氢钠 、 乙酰氯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 13.17h， 生成 Methyl 4-[(2-naphthylsulfonyl)amino]benzoate
  参考文献：
  名称：

  Discovery of a series of small molecules as potent histone deacetylase inhibitors

  摘要：

  A series of small molecules were designed and synthesized based on our previous virtual screening approach, which was performed to discover potent histone deacetylase inhibitors (HDACIs) with novel structures. The derived compounds were tested by Hela cell nucleus extract for enzyme inhibition assay. Tumor cell growth inhibition assays were performed using a series of tumor cell lines. Molecule 4h has the best performance among these compounds with enzyme inhibition IC50 of 0.14 mu M and tumor cell growth inhibition IC50 of 1.85 (U937), 2.02 (HL60), 2.67 (K562). Docking studies showed that multiple H-bonds and hydrophobic interactions make 4h binding to the active site of HDAC. 4h has the advantage of low molecular weight, so a variety of structural modifications can be performed in our further studies.

  DOI：

  10.3109/14756366.2013.780237

文献信息

• Discovery of a series of small molecules as potent histone deacetylase inhibitors
  作者：Lei Zhang、Xuejian Wang、Xiaoguang Li、Wenfang Xu

  DOI：10.3109/14756366.2013.780237

  日期：2014.6.1

  A series of small molecules were designed and synthesized based on our previous virtual screening approach, which was performed to discover potent histone deacetylase inhibitors (HDACIs) with novel structures. The derived compounds were tested by Hela cell nucleus extract for enzyme inhibition assay. Tumor cell growth inhibition assays were performed using a series of tumor cell lines. Molecule 4h has the best performance among these compounds with enzyme inhibition IC50 of 0.14 mu M and tumor cell growth inhibition IC50 of 1.85 (U937), 2.02 (HL60), 2.67 (K562). Docking studies showed that multiple H-bonds and hydrophobic interactions make 4h binding to the active site of HDAC. 4h has the advantage of low molecular weight, so a variety of structural modifications can be performed in our further studies.