N-[4-(carbomethoxy)phenyl] 4-fluorobenzenesulfonamide | 260968-85-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[4-(carbomethoxy)phenyl] 4-fluorobenzenesulfonamide
• 英文别名: Methyl 4-{[(4-fluorophenyl)sulfonyl]amino}benzoate；methyl 4-[(4-fluorophenyl)sulfonylamino]benzoate
• CAS: 260968-85-2
• 化学式: C₁₄H₁₂FNO₄S
• mdl: MFCD01213863
• 分子量: 309.318
• InChiKey: LTRIJQHUBIJVRD-UHFFFAOYSA-N

物化性质

• 沸点：
  445.0±55.0 °C(Predicted)
• 密度：
  1.401±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[4-(carbomethoxy)phenyl] 4-fluorobenzenesulfonamide 在 甲醇 、 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.5h， 生成 4-(4-fluorobenzenesulfonylamino)benzoic acid
  参考文献：
  名称：

  组织蛋白酶S的4-氨基呋喃-3-酮抑制剂的固相平行合成和SAR：磺酰胺P3取代基对效能和选择性的影响

  摘要：

  描述了组织蛋白酶S的高效和选择性的4-氨基呋喃-3-酮抑制剂。介绍了一系列在P3位置带有磺酰胺部分的抑制剂的合成及其构效关系。该系列的几个成员显示出对目标酶的亚纳摩尔抑制作用以及出色的选择性和良好的细胞效能。最有趣的抑制剂的分子模型描述了扩展S3口袋中的相互作用，并解释了观察到的对组织蛋白酶K的选择性。

  DOI：

  10.1016/j.bmc.2008.12.020
• 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 N-[4-(carbomethoxy)phenyl] 4-fluorobenzenesulfonamide
  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

• COMPOUNDS USEFUL AS AICARFT INHIBITORS
  申请人：AGOURON PHARMACEUTICALS, INC.

  公开号：EP1109560B1

  公开（公告）日：2003-08-27
• EP1109560A4
  申请人：——

  公开号：EP1109560A4

  公开（公告）日：2002-04-17
• US6525050B1
  申请人：——

  公开号：US6525050B1

  公开（公告）日：2003-02-25
• [EN] COMPOUNDS USEFUL AS AICARFT INHIBITORS<br/>[FR] COMPOSES UTILES EN TANT QU'INHIBITEURS D'AICARFT
  申请人：AGOURON PHARMA

  公开号：WO2000013688A1

  公开（公告）日：2000-03-16

  Coumpounds of the formula (I) (where R?1, R2, and R3¿ are as defined in the specification) are inhibitors of AICARFT. These compounds, as well as their pharmaceutically acceptable salts, solvates, prodrugs, and pharmaceutically active metabolites, are useful in pharmaceutical compositions for treating diseases such as cancer.
• 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.