3-[(dimethylamino)methyl]-6-[(E)-3-phenylprop-2-enoyl]-1,3-benzoxazol-2-one | 1002113-04-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-[(dimethylamino)methyl]-6-[(E)-3-phenylprop-2-enoyl]-1,3-benzoxazol-2-one
• CAS: 1002113-04-3
• 化学式: C₁₉H₁₈N₂O₃
• 分子量: 322.364
• InChiKey: LULWPMRHGJPILP-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 6-cinnamoyl-2(3H)benzoxazolone 、 二甲胺 以 乙醇 为溶剂， 反应 24.0h， 以53%的产率得到3-[(dimethylamino)methyl]-6-[(E)-3-phenylprop-2-enoyl]-1,3-benzoxazol-2-one
  参考文献：
  名称：

  Cytotoxic Mannich bases of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones

  摘要：

  A series of 12 new Mannich bases with chalcone core structure were synthesized as potential antineoplastic agents, via N-aminomethylation of two parent 6-(3 -aryl-2-propenoyl)-2(3 H)-benzoxazolones. The newly synthesized compounds as well as the chalcone prototypes were evaluated for cytotoxicity in the human pre-B-cell leukemia cell line BV-173 using the MTT-dye reduction assay. The tested compounds exhibited concentration-dependent cytotoxic effects at low micromolar concentrations. Ten of the Mannich bases characterized by significant activity in BV-173 were further evaluated against the chronic myeloid leukemia cell line K-562 and were found to suppress the growth of these cells at relatively higher concentrations as compared to the former tumor model. Selected Mannich bases induced programmed cell death in BV-173 at a concentration of 2.5 mu M as evidenced by the encountered DNA-laddering. Taken together our data suggest that the presented heterocyclic chalcone derived Mannich bases necessitate detailed pharmacological evaluation in order to define further the structure activity relationships, in a larger spectrum of tumor models and to elucidate the mechanisms implicated in the observed cytotoxic effects. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.02.019

文献信息

• Cytotoxic Mannich bases of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones
  作者：Y. Ivanova、G. Momekov、O. Petrov、M. Karaivanova、V. Kalcheva

  DOI：10.1016/j.ejmech.2007.02.019

  日期：2007.11

  A series of 12 new Mannich bases with chalcone core structure were synthesized as potential antineoplastic agents, via N-aminomethylation of two parent 6-(3 -aryl-2-propenoyl)-2(3 H)-benzoxazolones. The newly synthesized compounds as well as the chalcone prototypes were evaluated for cytotoxicity in the human pre-B-cell leukemia cell line BV-173 using the MTT-dye reduction assay. The tested compounds exhibited concentration-dependent cytotoxic effects at low micromolar concentrations. Ten of the Mannich bases characterized by significant activity in BV-173 were further evaluated against the chronic myeloid leukemia cell line K-562 and were found to suppress the growth of these cells at relatively higher concentrations as compared to the former tumor model. Selected Mannich bases induced programmed cell death in BV-173 at a concentration of 2.5 mu M as evidenced by the encountered DNA-laddering. Taken together our data suggest that the presented heterocyclic chalcone derived Mannich bases necessitate detailed pharmacological evaluation in order to define further the structure activity relationships, in a larger spectrum of tumor models and to elucidate the mechanisms implicated in the observed cytotoxic effects. (C) 2007 Elsevier Masson SAS. All rights reserved.