α-[(2-Nitro-1H-imidazol-1-yl)methyl]-7-aza-bicyclo[4.1.0]heptane-7-ethanol | 120277-90-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: α-[(2-Nitro-1H-imidazol-1-yl)methyl]-7-aza-bicyclo[4.1.0]heptane-7-ethanol
• 英文别名: alpha-[(2-Nitro-1H-imidazole-1-yl)methyl]-7-azabicyclo[4.1.0]heptane-7-ethanol；1-(7-azabicyclo[4.1.0]heptan-7-yl)-3-(2-nitroimidazol-1-yl)propan-2-ol
• CAS: 120277-90-9
• 化学式: C₁₂H₁₈N₄O₃
• 分子量: 266.3
• InChiKey: PYFVVJHOMNLKIO-UHFFFAOYSA-N

物化性质

• 熔点：
  88-89 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  509.5±60.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  86.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  α-[(2-Nitro-1H-imidazol-1-yl)methyl]-7-aza-bicyclo[4.1.0]heptane-7-ethanol 生成 1-[[(1R,2R)-2-bromocyclohexyl]amino]-3-(2-nitroimidazol-1-yl)propan-2-ol;hydrobromide
  参考文献：
  名称：

  SUTO, MARK J.;WERBEL, LESLIE M.

  摘要：

  DOI：
• 作为产物：
  描述：

  7-氮杂双环[4.1.0]庚烷 、 1-(2,3-环氧丙基)-2-硝基咪唑 以 甲醇 为溶剂， 反应 3.0h， 以80%的产率得到α-[(2-Nitro-1H-imidazol-1-yl)methyl]-7-aza-bicyclo[4.1.0]heptane-7-ethanol
  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

• 2-nitroimidazole derivatives useful as radiosensitizers for hypoxic
  申请人：Warner-Lambert Company

  公开号：US04797397A1

  公开（公告）日：1989-01-10

  Certain .alpha.-[(2-nitro-1H-imidazol-1-yl)methyl]-aziridinylethanols and the corresponding aziridine-ring opened analogs are useful as radiation sensitizers for X-irradiation therapy of tumors.

  某些 .alpha.-[(2-硝基-1H-咪唑-1-基)甲基]-环氧乙基乙醇及其相应的环氧乙基环开放类似物可用作肿瘤X射线治疗的辐射增敏剂。
• 2-nitroimidazole derivatives useful as radiosensitizers for hypoxic tumor cells
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0302416A1

  公开（公告）日：1989-02-08

  α-[(2-nitro-1H-imidazol-1-yl)methyl]-(A) azaridinylethanol derivatives of formula I and the corresponding aziridine-ring opened analogs are useful as radiation sensitizers for X-irradiation therapy of tumors.

  式 I 的α-[(2-硝基-1H-咪唑-1-基)甲基]-(A) 氮丙啶乙醇衍生物 和相应的氮丙啶开环类似物可用作 X 射线治疗肿瘤的辐射增敏剂。
• US4797397A
  申请人：——

  公开号：US4797397A

  公开（公告）日：1989-01-10