3-氧杂-7-氮杂双环[4.1.0]庚烷 | 333-10-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧氮杂卓类
• 中文名称: 3-氧杂-7-氮杂双环[4.1.0]庚烷
• 英文名称: 3-oxa-7-azabicyclo<4.1.0>heptne
• 英文别名: 3-Oxa-7-azabicyclo[4.1.0]heptane
• CAS: 333-10-8
• 化学式: C₅H₉NO
• 分子量: 99.1326
• InChiKey: DIUNZTQKLKGEBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  31.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-氧杂-7-氮杂双环[4.1.0]庚烷 在 氢溴酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.0h， 生成 trans-α-<<(4-bromotetrahydro-2H-pyran-3-yl)amino>methyl>-2-nitro-1H-imidazole-1-ethanol hydrobromide
  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
• 作为产物：
  描述：

  4-四氢吡喃基 甲磺酸酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 3-氧杂-7-氮杂双环[4.1.0]庚烷
  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

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.