N,N-二甲基-2-硝基-1-咪唑乙酰胺 | 22668-03-7

• 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
• 中文名称: N,N-二甲基-2-硝基-1-咪唑乙酰胺
• 英文名称: KIN-806
• 英文别名: N,N-dimethyl-2-(2-nitro-imidazol-1-yl)-acetamide；N,N-Dimethyl-2-nitro-1-imidazoleacetamide；N,N-dimethyl-2-(2-nitroimidazol-1-yl)acetamide
• CAS: 22668-03-7
• 化学式: C₇H₁₀N₄O₃
• 分子量: 198.181
• InChiKey: NXUUXBZRCPNIBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  84
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933290090

反应信息

• 作为产物：
  描述：

  二甲胺 、 1-乙氧基甲基-1H-咪唑 以 甲醇 为溶剂， 反应 18.5h， 以87%的产率得到N,N-二甲基-2-硝基-1-咪唑乙酰胺
  参考文献：
  名称：

  New antimetastatic hypoxic cell radiosensitizers: design, synthesis, and biological activities of 2-nitroimidazole-acetamide, TX-1877, and its analogues

  摘要：

  We designed, based on the molecular orbital (MO) calculation, synthesized, and evaluated the biological activities of the new antimetastatic hypoxic cell radiosensitizer, 2-nitroimidazole-acetamide, TX-1877. and its analogues. Each analogue has an electron-affinic imidazole group, an acetamide group and a certain hydrophilic group to control its biological effect, toxicity, and pharmacokinetics. In in vitro radiosensitization assay, most TX-1877 analogues, which have an electron affinity (EA) of more than 0.9 eV and partition coefficient (P) of more than 0.021, showed satisfactory enhancement ratios (ER > 1.60) at doses of 1 mM. On the other hand, imidazole analogues, such as TX-1908 (EA = 0.67 eV), TX-1910 (EA = -0.34 eV) and TX-1931 (EA = -0.37 eV), which have low electron affinities, had an ER of 1.31 or less. TX-1877 and KIN-806 effectively inhibited tumor regrowth when administered with irradiation in vivo at a dose of 0.4 mg/g. Tumor lung metastasis: was inhibited by treatment with either TX-1877 or KIN-806 without irradiation at a dose of 0.4 mg/g. TX-1877 reduced markedly the mean number of metastatic lung nodules in comparison with KIN-806. Moreover, TX-1877 and KIN-806 enhanced macrophage and helper T lymphocyte infiltration for 3 weeks after drug treatment. TX-1877 shows a high EA value and has the C-2 of HOMO localizing on N-methylamide and the C-2 of LUMO localizing on 2-nitroimidazole group. The MO data might be useful fbr designing 3 bifunctional hypoxic cell radiosensitizer. TX-1877 and its analogues are potential antimetastatic hypoxic cell radiosensitizers. which would improve the efficiency of radiotherapy and quality of life in cancer treatment. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00265-0

文献信息

• PROCESSES FOR NITRATION OF N-SUBSTITUTED IMIDAZOLES
  申请人：Rajaraman Shanthi

  公开号：US20080045722A1

  公开（公告）日：2008-02-21

  The present invention relates to a process for making 2 -nitroimidazoles that involves the selective nitration of N-substituted imidazoles.

  本发明涉及一种制备2-硝基咪唑的方法，其中包括对N-取代咪唑进行选择性硝化。
• US7608725B2
  申请人：——

  公开号：US7608725B2

  公开（公告）日：2009-10-27
• [EN] PROCESSES FOR NITRATION OF N-SUBSTITUTED IMIDAZOLES<br/>[FR] PROCÉDÉS DE NITRATION D'IMIDAZOLES N-SUBSTITUÉES
  申请人：RICHARD STOCKTON COLLEGE OF NE

  公开号：WO2007134187A2

  公开（公告）日：2007-11-22

  [EN] The present invention relates to a process for making 2-nitroimidazoles that involves the selective nitration of N-suhstituted imidazoles.
  [FR] L'invention concerne un procédé de préparation de 2-nitroimidazoles faisant intervenir la nitration sélective d'imidazoles N-substituées.
• New antimetastatic hypoxic cell radiosensitizers: design, synthesis, and biological activities of 2-nitroimidazole-acetamide, TX-1877, and its analogues
  作者：Soko Kasai、Hideko Nagasawa、Mao Yamashita、Mie Masui、Hideki Kuwasaka、Tomoko Oshodani、Yoshihiro Uto、Taisuke Inomata、Shigenori Oka、Seiichi Inayama、Hitoshi Hori

  DOI：10.1016/s0968-0896(00)00265-0

  日期：2001.2

  We designed, based on the molecular orbital (MO) calculation, synthesized, and evaluated the biological activities of the new antimetastatic hypoxic cell radiosensitizer, 2-nitroimidazole-acetamide, TX-1877. and its analogues. Each analogue has an electron-affinic imidazole group, an acetamide group and a certain hydrophilic group to control its biological effect, toxicity, and pharmacokinetics. In in vitro radiosensitization assay, most TX-1877 analogues, which have an electron affinity (EA) of more than 0.9 eV and partition coefficient (P) of more than 0.021, showed satisfactory enhancement ratios (ER > 1.60) at doses of 1 mM. On the other hand, imidazole analogues, such as TX-1908 (EA = 0.67 eV), TX-1910 (EA = -0.34 eV) and TX-1931 (EA = -0.37 eV), which have low electron affinities, had an ER of 1.31 or less. TX-1877 and KIN-806 effectively inhibited tumor regrowth when administered with irradiation in vivo at a dose of 0.4 mg/g. Tumor lung metastasis: was inhibited by treatment with either TX-1877 or KIN-806 without irradiation at a dose of 0.4 mg/g. TX-1877 reduced markedly the mean number of metastatic lung nodules in comparison with KIN-806. Moreover, TX-1877 and KIN-806 enhanced macrophage and helper T lymphocyte infiltration for 3 weeks after drug treatment. TX-1877 shows a high EA value and has the C-2 of HOMO localizing on N-methylamide and the C-2 of LUMO localizing on 2-nitroimidazole group. The MO data might be useful fbr designing 3 bifunctional hypoxic cell radiosensitizer. TX-1877 and its analogues are potential antimetastatic hypoxic cell radiosensitizers. which would improve the efficiency of radiotherapy and quality of life in cancer treatment. (C) 2001 Elsevier Science Ltd. All rights reserved.