NSC 310455 | 74141-74-5

• 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: NSC 310455
• 英文别名: N,N-di-(2-hydroxyethyl)-2-(2-nitro-1-imidazolyl) acetamide；1H-Imidazole-1-acetamide, N,N-bis(2-hydroxyethyl)-2-nitro-；N,N-bis(2-hydroxyethyl)-2-(2-nitroimidazol-1-yl)acetamide
• CAS: 74141-74-5
• 化学式: C₉H₁₄N₄O₅
• 分子量: 258.234
• InChiKey: KGFGBSRVWKBWIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  依他硝唑 生成 NSC 310455
  参考文献：
  名称：

  Nitroimidazoles of low toxicity and high activity as radiosensitizers of

  摘要：

  据报道，由公式##STR1##表示的两种化合物，其中R为氢或2-羟乙基基团，据称在大脑和神经组织中具有最小渗透性，同时在低氧肿瘤细胞中具有最大渗透性。这些化合物具有这些性质的结合使其成为电子亲和性1-取代的2-硝基咪唑类化合物中最佳的放射增敏剂。

  公开号：

  US04371540A1

文献信息

• 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.
• US4371540A
  申请人：——

  公开号：US4371540A

  公开（公告）日：1983-02-01
• Nitroimidazoles of low toxicity and high activity as radiosensitizers of
  申请人：The United States of America as represented by the Secretary of the

  公开号：US04371540A1

  公开（公告）日：1983-02-01

  Two compounds represented by the formula ##STR1## wherein R is hydrogen or a 2-hydroxyethyl radical are reported to have minimum penetration into the brain and nerve tissues combined with maximum penetration into hypoxic tumor cells. This combination of properties makes these compounds the optimal radiosensitizers among electron-affinic 1-substituted 2-nitroinidazoles.

  据报道，由公式##STR1##表示的两种化合物，其中R为氢或2-羟乙基基团，据称在大脑和神经组织中具有最小渗透性，同时在低氧肿瘤细胞中具有最大渗透性。这些化合物具有这些性质的结合使其成为电子亲和性1-取代的2-硝基咪唑类化合物中最佳的放射增敏剂。