3-acetylamino-N-(4-nitrophenyl)benzamide | 926619-09-2

• 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: 3-acetylamino-N-(4-nitrophenyl)benzamide
• 英文别名: 3-(acetylamino)-N-(4-nitrophenyl)benzamide；3-acetamido-N-(4-nitrophenyl)benzamide
• CAS: 926619-09-2
• 化学式: C₁₅H₁₃N₃O₄
• 分子量: 299.286
• InChiKey: XPENDOYEAIFPCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-acetylamino-N-(4-nitrophenyl)benzamide 在 盐酸 作用下， 以 1,4-二氧六环 、 乙二醇乙醚 、 水 为溶剂， 反应 7.0h， 生成 3-[(2-氨基-6-甲基-4-嘧啶基)氨基]-N-(4-硝基苯基)苯甲酰胺盐酸盐
  参考文献：
  名称：

  Structure–activity relationships for 4-anilinoquinoline derivatives as inhibitors of the DNA methyltransferase enzyme DNMT1

  摘要：

  A series of 4-anilinoquinoline derivatives related to the known inhibitor SGI-1027, containing side chains of varying pK(a), were prepared by acid-catalysed coupling of the pre-formed side chains with 4-chloroquinolines. The compounds were evaluated for their ability to reduce the level of DNMT1 protein in HCT116 human colon carcinoma cells by Western blotting. With a very strongly basic N-methylpyridinium side chain, only NHCO-linked compounds were effective, whereas less strongly basic ((diaminomethylene) hydrazono)ethyl or 3-methylpyrimidine-2,4-diamine side chains allowed both NHCO- and CONH-linked compounds to show activity. In contrast, the pK(a) of the quinoline unit had little apparent influence on activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.033
• 作为产物：
  描述：

  3-乙酰氨基苯甲酸 、 4-硝基苯胺 在 N,N'-羰基二咪唑 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 6.0h， 以55%的产率得到3-acetylamino-N-(4-nitrophenyl)benzamide
  参考文献：
  名称：

  Structure–activity relationships for 4-anilinoquinoline derivatives as inhibitors of the DNA methyltransferase enzyme DNMT1

  摘要：

  A series of 4-anilinoquinoline derivatives related to the known inhibitor SGI-1027, containing side chains of varying pK(a), were prepared by acid-catalysed coupling of the pre-formed side chains with 4-chloroquinolines. The compounds were evaluated for their ability to reduce the level of DNMT1 protein in HCT116 human colon carcinoma cells by Western blotting. With a very strongly basic N-methylpyridinium side chain, only NHCO-linked compounds were effective, whereas less strongly basic ((diaminomethylene) hydrazono)ethyl or 3-methylpyrimidine-2,4-diamine side chains allowed both NHCO- and CONH-linked compounds to show activity. In contrast, the pK(a) of the quinoline unit had little apparent influence on activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.033

文献信息

• WO2008/46085
  申请人：——

  公开号：——

  公开（公告）日：——