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1-Azetidin-1-yl-3-(2-nitro-imidazol-1-yl)-propan-2-ol | 134419-50-4

中文名称
——
中文别名
——
英文名称
1-Azetidin-1-yl-3-(2-nitro-imidazol-1-yl)-propan-2-ol
英文别名
1-(Azetidin-1-yl)-3-(2-nitroimidazol-1-yl)propan-2-ol
1-Azetidin-1-yl-3-(2-nitro-imidazol-1-yl)-propan-2-ol化学式
CAS
134419-50-4
化学式
C9H14N4O3
mdl
——
分子量
226.235
InChiKey
CPWNPAJUGFNFQV-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):
    0.3
  • 重原子数:
    16
  • 可旋转键数:
    4
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.67
  • 拓扑面积:
    87.1
  • 氢给体数:
    1
  • 氢受体数:
    5

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:
    描述:
    杂氮环丁烷1-(2,3-环氧丙基)-2-硝基咪唑甲醇 为溶剂, 反应 3.0h, 以52%的产率得到1-Azetidin-1-yl-3-(2-nitro-imidazol-1-yl)-propan-2-ol
    参考文献:
    名称:
    A new class of analog of the bifunctional radiosensitizer .alpha.-(1-aziridinylmethyl)-2-nitro-1H-imidazole-1-ethanol (RSU 1069): the cycloalkylaziridines
    摘要:
    A series of compounds related to alpha-(1-aziridinylmethyl)-2-nitro-1H-imidazole-1-ethanol (RSU 1069, 1) were synthesized and evaluated as selective hypoxic cell cytotoxic agents and as radiosensitizers. The aziridine moiety was replaced with a number of other potential alkylating groups including cycloalkylaziridines and azetidines. The data indicated that modification of the aziridine of 1 resulted in a substantial decrease in the ability of the compounds to selectively kill hypoxic cells. However, these modifications did not affect the compounds' in vitro radiosensitizing activity since many of the derivatives were as potent as 1. All of the compounds that were evaluated in vivo were less toxic than 1, and several members of this series had significant activity. The best compound was trans-alpha-[[(4-bromotetrahydro-2H-pyran-3-yl)amino]methyl]-2-nitro-1H-imidazole-1-ethanol (18), which, due to its activity and log P value, is a candidate for additional in vivo studies.
    DOI:
    10.1021/jm00112a026
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文献信息

  • A new class of analog of the bifunctional radiosensitizer .alpha.-(1-aziridinylmethyl)-2-nitro-1H-imidazole-1-ethanol (RSU 1069): the cycloalkylaziridines
    作者:Mark J. Suto、Michael A. Stier、Leslie M. Werbel、Carla M. Arundel-Suto、Wilbur R. Leopold、William E. Elliott、Judith S. Sebolt-Leopold
    DOI:10.1021/jm00112a026
    日期:1991.8
    A series of compounds related to alpha-(1-aziridinylmethyl)-2-nitro-1H-imidazole-1-ethanol (RSU 1069, 1) were synthesized and evaluated as selective hypoxic cell cytotoxic agents and as radiosensitizers. The aziridine moiety was replaced with a number of other potential alkylating groups including cycloalkylaziridines and azetidines. The data indicated that modification of the aziridine of 1 resulted in a substantial decrease in the ability of the compounds to selectively kill hypoxic cells. However, these modifications did not affect the compounds' in vitro radiosensitizing activity since many of the derivatives were as potent as 1. All of the compounds that were evaluated in vivo were less toxic than 1, and several members of this series had significant activity. The best compound was trans-alpha-[[(4-bromotetrahydro-2H-pyran-3-yl)amino]methyl]-2-nitro-1H-imidazole-1-ethanol (18), which, due to its activity and log P value, is a candidate for additional in vivo studies.
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