(E)-2-(2-cyano-3-((5-(4-chlorobenzyl)-1,3,4-thiadiazol-2-yl)amino)-3-oxoprop-1-en-1-yl)phenyl 2-nitrobenzenesulfonate

• 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: (E)-2-(2-cyano-3-((5-(4-chlorobenzyl)-1,3,4-thiadiazol-2-yl)amino)-3-oxoprop-1-en-1-yl)phenyl 2-nitrobenzenesulfonate
• 英文别名: [2-[(E)-3-[[5-[(4-chlorophenyl)methyl]-1,3,4-thiadiazol-2-yl]amino]-2-cyano-3-oxoprop-1-enyl]phenyl] 2-nitrobenzenesulfonate
• 化学式: C₂₅H₁₆ClN₅O₆S₂
• 分子量: 582.017
• InChiKey: BEUCBDAONCDBLZ-NBVRZTHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  165.18
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  2-氨基-5-(4-氯苄基)-1,3,4-噻二唑 在 ammonium acetate 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 8.33h， 生成 (E)-2-(2-cyano-3-((5-(4-chlorobenzyl)-1,3,4-thiadiazol-2-yl)amino)-3-oxoprop-1-en-1-yl)phenyl 2-nitrobenzenesulfonate
  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

文献信息

• Synthesis of (1,3,4-thiadiazol-2-yl)-acrylamide derivatives as potential antitumor agents against acute leukemia cells
  作者：Qing Li、Ran An、Yaochun Xu、Mi Zhou、Yan Li、Chun Guo、Renxiao Wang

  DOI：10.1016/j.bmcl.2020.127114

  日期：2020.5

  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.