3-(3-amino-phenyl)-2-cyano-acrylic acid ethyl ester | 113785-09-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(3-amino-phenyl)-2-cyano-acrylic acid ethyl ester
• 英文别名: 3-Amino-α-cyan-zimtsaeureaethylester；3-Amino-benzalmalonsaeure-aethylester-nitril；3-(3-Amino-phenyl)-2-cyan-acrylsaeure-aethylester；ethyl (E)-3-(3-aminophenyl)-2-cyanoprop-2-enoate
• CAS: 113785-09-4
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: TUHHWNOLIIAHGZ-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-amino-phenyl)-2-cyano-acrylic acid ethyl ester 在 吡啶 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (E)-2-cyano-3-(3-(p-fluorophenylsulfonylamino)phenyl)-N-(5-(thiophen-2-yl) -1,3,4-thiadiazol-2-yl)acrylamide
  参考文献：
  名称：

  Synthesis of (1,3,4-thiadiazol-2-yl)-acrylamide derivatives as potential antitumor agents against acute leukemia cells

  摘要：

  A lead compound with the (1,3,4-thiadiazol-2-yl) acrylamide scaffold was discovered to have significant cytotoxicity on several tumor cell lines in an in-house cell-based screening. A total of 60 derivative compounds were then synthesized and tested in a CCK-8 cell viability assay. Some of them exhibited improved cytotoxic activities. The most potent compounds had IC50, values of 1-5 mu M on two acute leukemia tumor cell lines, i.e. RS4;11 and HL-60. Flow cytometry analysis of several active compounds and detection of caspase activation indicated that they induced caspase-dependent apoptosis. It was also encouraging to observe that these compounds did not have obvious cytotoxicity on normal cells, i.e. IC50 > 50 mu M on HEK-293T cells. Although the molecular targets of this class of compound are yet to be revealed, our current results suggest that this class of compound represents a new possibility for developing drug candidates against acute leukemia.

  DOI：

  10.1016/j.bmcl.2020.127114
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 tin(ll) chloride 作用下， 生成 3-(3-amino-phenyl)-2-cyano-acrylic acid ethyl ester
  参考文献：
  名称：

  Kauffmann, Chemische Berichte, 1916, vol. 49, p. 1324

  摘要：

  DOI：

文献信息

• Kauffmann, Chemische Berichte, 1916, vol. 49, p. 1336
  作者：Kauffmann

  DOI：——

  日期：——