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2-bromo-N-{3-[3-(4-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-6-yl]phenyl}acrylamide

中文名称
——
中文别名
——
英文名称
2-bromo-N-{3-[3-(4-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-6-yl]phenyl}acrylamide
英文别名
2-bromo-N-[3-[3-(4-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-6-yl]phenyl]prop-2-enamide
2-bromo-N-{3-[3-(4-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-6-yl]phenyl}acrylamide化学式
CAS
——
化学式
C21H16BrN3O2S
mdl
——
分子量
454.347
InChiKey
HGDQUFSDVNLDHE-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    5.8
  • 重原子数:
    28
  • 可旋转键数:
    5
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.05
  • 拓扑面积:
    83.9
  • 氢给体数:
    1
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    参考文献:
    名称:
    Design, synthesis and antiproliferative activity of novel heterobivalent hybrids based on imidazo[2,1- b ][1,3,4]thiadiazole and imidazo[2,1- b ][1,3]thiazole scaffolds
    摘要:
    Heterobivalent ligands constituted by two different pharmacophores that bind to different molecular targets or to two distinct sites on the same molecular target could be one of the methods used for the treatment of cancer. In view of the importance of imidazo[1,2-6][1,3]thiazole and imidazo[1,2-b][1,3,4] thiadiazole as privileged structures for the preparation of novel anticancer agents, we decided to explore the synthesis and biological evaluation of molecular conjugates comprising these fused bicyclic systems tethered at their C-6 position by a meta-(alpha-bromoacryloylamido)phenyl moiety. We found that most of the hybrid compounds displayed high antiproliferative activity toward a wide panel of cancer cell lines, with one-digit micromolar to submicromolar 50% inhibitory concentrations (IC50). We have observed that selected compounds 7d, 7e, 7n and 8c induced apoptosis, which was associated with the release of cytochrome c and cleavage of multiple caspases. Overexpression of the protective mitochondrial protein Bcl-2 did not confer protection to cell death induced by these compounds. (C) 2015 Elsevier Masson SAS. All rights reserved.
    DOI:
    10.1016/j.ejmech.2015.06.042
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文献信息

  • Design, synthesis and antiproliferative activity of novel heterobivalent hybrids based on imidazo[2,1- b ][1,3,4]thiadiazole and imidazo[2,1- b ][1,3]thiazole scaffolds
    作者:Romeo Romagnoli、Pier Giovanni Baraldi、Filippo Prencipe、Jan Balzarini、Sandra Liekens、Francisco Estévez
    DOI:10.1016/j.ejmech.2015.06.042
    日期:2015.8
    Heterobivalent ligands constituted by two different pharmacophores that bind to different molecular targets or to two distinct sites on the same molecular target could be one of the methods used for the treatment of cancer. In view of the importance of imidazo[1,2-6][1,3]thiazole and imidazo[1,2-b][1,3,4] thiadiazole as privileged structures for the preparation of novel anticancer agents, we decided to explore the synthesis and biological evaluation of molecular conjugates comprising these fused bicyclic systems tethered at their C-6 position by a meta-(alpha-bromoacryloylamido)phenyl moiety. We found that most of the hybrid compounds displayed high antiproliferative activity toward a wide panel of cancer cell lines, with one-digit micromolar to submicromolar 50% inhibitory concentrations (IC50). We have observed that selected compounds 7d, 7e, 7n and 8c induced apoptosis, which was associated with the release of cytochrome c and cleavage of multiple caspases. Overexpression of the protective mitochondrial protein Bcl-2 did not confer protection to cell death induced by these compounds. (C) 2015 Elsevier Masson SAS. All rights reserved.
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