5-甲基-7-氮杂双环[4.1.0]庚烷 | 55903-15-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 中文名称: 5-甲基-7-氮杂双环[4.1.0]庚烷
• 英文名称: 2-methyl-7-aza-bicyclo[4.1.0]heptane
• 英文别名: 7-Azabicyclo[4.1.0]heptane, 2-methyl-；2-methyl-7-azabicyclo[4.1.0]heptane
• CAS: 55903-15-6
• 化学式: C₇H₁₃N
• 分子量: 111.187
• InChiKey: SHVUCHAWQPEOLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 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：
  21.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-甲基-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56%的产率得到2-methyl-α-[(2-nitro-1H-imidazol-1-yl)methyl]-7-azabicyclo[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
• 作为产物：
  描述：

  E-3-methyl-2-cyclohexenone oxime 以23%的产率得到
  参考文献：
  名称：

  GIRAULT, Y.;DECOUZON, M.;AZZARO, M., TETRAHEDRON LETT., 1984, 25, N 26, 2763-2766

  摘要：

  DOI：

文献信息

• 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。
• Synthese d'aziridines N-non substituees par reduction de sels d'hydrazonium
  作者：Yvonne Girault、Michèle Decouzon、Marcel Azzaro

  DOI：10.1016/s0040-4039(01)81284-3

  日期：——
• US4797397A
  申请人：——

  公开号：US4797397A

  公开（公告）日：1989-01-10
• 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.
• GIRAULT, Y.;DECOUZON, M.;AZZARO, M., TETRAHEDRON LETT., 1984, 25, N 26, 2763-2766
  作者：GIRAULT, Y.、DECOUZON, M.、AZZARO, M.

  DOI：——

  日期：——