1H-Indole-3-propanamide, alpha-amino-N-(4-bromophenyl)- | 1163686-88-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1H-Indole-3-propanamide, alpha-amino-N-(4-bromophenyl)-
• 英文别名: 2-amino-N-(4-bromophenyl)-3-(1H-indol-3-yl)propanamide
• CAS: 1163686-88-1
• 化学式: C₁₇H₁₆BrN₃O
• 分子量: 358.238
• InChiKey: BPADBHVRSSENMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  70.9
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1H-Indole-3-propanamide, alpha-amino-N-(4-bromophenyl)- 、 (E)-4-(3-ethoxy-3-oxoprop-1-en-1-yl)benzoic acid 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以46.8%的产率得到ethyl (E)-3-(4-((1-((4-bromophenyl)amino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)carbamoyl)phenyl)acrylate
  参考文献：
  名称：

  Design, synthesis and activity evaluation of indole-based double – Branched HDAC1 inhibitors

  摘要：

  Histone deacetylases inhibitors (HDACIs) represents effective treatments for cancer. In continuing our efforts to develop novel and potent HDACIs, a series of N-hydroxycinnamamide-based HDACIs with aromatic ring and various aliphatic linker have been successfully designed and synthesized. Biological evaluations established that compounds 4h, 4i, 4j, 4l, 4r showed superior inhibition on histone deacetylase and antiproliferative activity in some solid tumor cell lines [HeLa, SK-N-BE(2), PC-3] compared to the known inhibitor SAHA. Among these analogs, 4l exhibited selectivity to HDAC1.

  DOI：

  10.1016/j.bmc.2019.03.008

文献信息

• Design, synthesis and activity evaluation of indole-based double – Branched HDAC1 inhibitors
  作者：Qiuqiong Zhang、Jiahui Lv、Feng He、Chenggong Yu、Ying Qu、Xiangna Zhang、Ana Xu、Jingde Wu

  DOI：10.1016/j.bmc.2019.03.008

  日期：2019.4

  Histone deacetylases inhibitors (HDACIs) represents effective treatments for cancer. In continuing our efforts to develop novel and potent HDACIs, a series of N-hydroxycinnamamide-based HDACIs with aromatic ring and various aliphatic linker have been successfully designed and synthesized. Biological evaluations established that compounds 4h, 4i, 4j, 4l, 4r showed superior inhibition on histone deacetylase and antiproliferative activity in some solid tumor cell lines [HeLa, SK-N-BE(2), PC-3] compared to the known inhibitor SAHA. Among these analogs, 4l exhibited selectivity to HDAC1.