3-<2-(2-nitro-1H-imidazol-1-yl)ethyl>-2-oxazolidinone | 131504-99-9

• 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: 3-<2-(2-nitro-1H-imidazol-1-yl)ethyl>-2-oxazolidinone
• 英文别名: 3-[2-(2-nitro-1H-imidazol-1-yl)ethyl]-2-oxazolidinone；3-[2-(2-nitroimidazol-1-yl)ethyl]-1,3-oxazolidin-2-one
• CAS: 131504-99-9
• 化学式: C₈H₁₀N₄O₄
• 分子量: 226.192
• InChiKey: ONYDUENBFGIDAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-<2-(2-nitro-1H-imidazol-1-yl)ethyl>-2-oxazolidinone 在 氢溴酸 、 溶剂黄146 作用下， 反应 18.0h， 以54%的产率得到N-(2-bromoethyl)-2-nitro-1H-imidazole-1-ethanamine monohydrobromide
  参考文献：
  名称：

  Dual-function radiosensitizers. .alpha.-[[(2-Bromoethyl)amino]methyl]-2-nitro-1H-imidazole-1-ethanol and related compounds: preparation via an aziridine equivalent

  摘要：

  An improved synthesis of the dual-function radiosensitizer alpha-[[2-bromoethyl)amino]methyl]-2-nitro-H-1-imidazole-1-ethanol (2, RB 6145) has been developed. Previously, the synthetic difficulties associated with this compound limited its attractiveness as a clinical candidate, although its radiosensitizing activity in preclinical models warranted its further development. The synthesis described uses a 2-oxazolidinone as an aziridine equivalent and provides 2 in 47% yield.

  DOI：

  10.1021/jm00107a047
• 作为产物：
  描述：

  3-(2-氯乙基)-2-噁唑烷酮 、 2-硝基咪唑 在 potassium carbonate 作用下， 生成 3-<2-(2-nitro-1H-imidazol-1-yl)ethyl>-2-oxazolidinone
  参考文献：
  名称：

  Dual-function radiosensitizers. .alpha.-[[(2-Bromoethyl)amino]methyl]-2-nitro-1H-imidazole-1-ethanol and related compounds: preparation via an aziridine equivalent

  摘要：

  An improved synthesis of the dual-function radiosensitizer alpha-[[2-bromoethyl)amino]methyl]-2-nitro-H-1-imidazole-1-ethanol (2, RB 6145) has been developed. Previously, the synthetic difficulties associated with this compound limited its attractiveness as a clinical candidate, although its radiosensitizing activity in preclinical models warranted its further development. The synthesis described uses a 2-oxazolidinone as an aziridine equivalent and provides 2 in 47% yield.

  DOI：

  10.1021/jm00107a047
• 作为试剂：
  描述：

  2-硝基咪唑 、 potassium carbonate 、 3-(2-氯乙基)-2-噁唑烷酮 在 氯仿 、 水 、 乙醇 、 3-<2-(2-nitro-1H-imidazol-1-yl)ethyl>-2-oxazolidinone 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 以to give 3.5 g (35%) of the desired product, 3-[2-(2-nitro-1H-imidazol-1-yl)ethyl]-2-oxazolidinone的产率得到3-<2-(2-nitro-1H-imidazol-1-yl)ethyl>-2-oxazolidinone
  参考文献：
  名称：

  Process for the synthesis of novel and known nitroimidazoles which are

  摘要：

  本发明是一种制备已知和新型硝基咪唑的新型工艺，具有新型中间体。该工艺优点是减少了工艺步骤的数量，提高了产量，同时在产品的立体异构体方面提供了更大的安全性和控制性。

  公开号：

  US05073639A1

文献信息

• Haloalkylaminomethyl-2-nitro-1H-imidazoles
  申请人：Warner-Lambert Company

  公开号：US04954515A1

  公开（公告）日：1990-09-04

  The present invention is novel nitroimidazoles useful as radiosensitizing or chemosensitizing agents in the treatment of hypoxic tumor cells. Also, the present invention is a novel process for preparing both known and novel nitroimidazoles having novel intermediates. The process advantageously reduces the number of process steps, provides increased yield with both greater safety and greater control of stereo-isomerism in the products.

  本发明是一种新型的硝基咪唑类化合物，可用作放射增敏剂或化学增敏剂，用于治疗缺氧肿瘤细胞。此外，本发明还涉及一种新型的制备已知和新型硝基咪唑类化合物的方法，其中包含新型的中间体。该方法具有优势，可以减少制程步骤的数量，提高产量，并且在产品中提供更大的安全性和对立体异构体的更大控制。
• 2-oxazolidinone derivatives of nitroimidazoles and pharmaceutical
  申请人：Warner-Lambert Company

  公开号：US05036089A1

  公开（公告）日：1991-07-30

  The present invention is novel 2-oxazolidinone analogs of nitroimidazoles; novel pharmaceutical compositions of selected analogs thereof and methods of use for the compositions as radiosensitizing or chemosensitizing agents in the treatment of hypoxic tumor cells.

  本发明是一种新型的硝基咪唑类2-噁唑烷酮类似物；所选类似物的新型药物组合物和使用该组合物作为放射增敏或化学增敏剂治疗低氧肿瘤细胞的方法。
• Aziridino derivatives of nitroimidazoles and pharmaceutical compositions
  申请人：Warner-Lambert Company

  公开号：US05036096A1

  公开（公告）日：1991-07-30

  The present invention is novel aziridino derivatives of nitroimidazoles and pharmaceutical compositions of selected derivatives useful as radiosensitizing or chemosensitizing agents in the treatment of hypoxic tumor cells. Also, the present invention is a novel process for preparing both known and novel aziridino derivatives of nitroimidazoles having novel intermediates.

  本发明涉及新型的硝基咪唑环丙胺衍生物及其选择性衍生物的药物组合物，用于放射增敏或化学增敏剂治疗低氧肿瘤细胞。此外，本发明还涉及一种新型方法，用于制备已知和新型的硝基咪唑环丙胺衍生物，其中包括新型中间体。
• A new process for the synthesis of novel and known nitroimidazoles which are useful as sensitizing agents
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0375951A1

  公开（公告）日：1990-07-04

  The present invention is novel nitroimidazoles useful as radiosensitizing or chemosensitizing agents in the treatment of hypoxic tumor cells. Also, the present invention is a novel process for preparing both known and novel nitroimidazoles having novel intermediates. The process advantageously reduces the number of process steps, provides increased yield with both greater safety and greater control of stereoisomerism in the products.

  本发明是新型硝基咪唑，可用作治疗缺氧性肿瘤细胞的放射增敏剂或化疗增敏剂。此外，本发明是一种新型工艺，用于制备具有新型中间体的已知和新型硝基咪唑。该工艺的优点是减少了工艺步骤的数量，提高了产率，同时提高了安全性，并能更好地控制产品的立体异构性。
• SUTO, MARK J.;STIER, MICHAEL A.;WERBEL, LESLIE M., J. MED. CHEM., 34,(1991) N, C. 1207-1209
  作者：SUTO, MARK J.、STIER, MICHAEL A.、WERBEL, LESLIE M.

  DOI：——

  日期：——