3-(4-nitro-1-imidazolyl)propionic acid | 145192-61-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-nitro-1-imidazolyl)propionic acid
• 英文别名: 3-(4-nitroimidazol-1-yl)propionic acid；3-(4-nitro-1H-imidazol-1-yl)propanoic acid；3-(4-nitroimidazol-1-yl)propanoic acid
• CAS: 145192-61-6
• 化学式: C₆H₇N₃O₄
• mdl: MFCD09802185
• 分子量: 185.139
• InChiKey: FZUTUMDUNFEAOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-nitro-1-imidazolyl)propionic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 22.0h， 生成 N-methyl-2-(3-(2-(2-(3-(4-nitro-1H-imidazol-1-yl)propanoyl)hydrazine-1-carbonothioyl)hydrazineylidene)butan-2-ylidene)hydrazine-1-carbothioamide
  参考文献：
  名称：

  Nitroimidazole conjugates of bis(thiosemicarbazonato)64Cu(II) – Potential combination agents for the PET imaging of hypoxia

  摘要：

  Combination agents comprising two different pharmacophores with the same biological target have the potential to show additive or synergistic activity. Bis(thiosemicarbazonato)copper(II) complexes (e.g. Cu-64-ATSM) and nitroimidazoles (e.g. F-18-MISO) are classes of tracer used for the delineation of tumor hypoxia by positron emission tomography (PET). Three nitroimidazole-bis(thiosemicarbazonato)copper(II) conjugates were produced in order to investigate their potential as combination hypoxia imaging agents. Two were derived from the known bifunctional bis(thiosemicarbazone) H(2)ATSM/A and the third from the new precursor diacetyl-2-(4-N-methyl-3-thiosemicarbazone)-3-(4-N-ethylamino-3-thiosemicarbazone) - H(2)ATSM/en. Oxygen-dependent uptake studies were performed using the Cu-64 radiolabelled complexes in EMT6 carcinoma cells. All the complexes displayed appreciable hypoxia selectivity, with the nitroimidazole conjugates displaying greater selectivity than a simple propyl derivative used as a control. Participation of the nitroimidazole group in the trapping mechanism is indicated by the increased hypoxic uptake of the 2- vs. the 4-substituted Cu-64-ATSM/A derivatives. The 2-nitroimidazole derivative of Cu-64-ATSM/en demonstrated superior hypoxia selectivity to Cu-64-ATSM over the range of oxygen concentrations tested. Biodistribution of the radiolabelled 2-nitroimidazole conjugates was carried out in EMT6 tumor-bearing mice. The complexes showed significantly different uptake trends in comparison to each other and previously studied Cu-ATSM derivatives. Uptake of the Cu-ATSM/en conjugate in non-target organs was considerably lower than for derivatives based on Cu-ATSM/A. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2009.10.009

文献信息

• Metal complexes as radiosensitizers: Cobalt(II), copper(II), rhodium(II) and platinum(II) complexes of 3-(1-imidazoyl)propionic acid and some nitro-substituted derivatives, and the crystal structure and radiosensitizer activity of [CuL2(H2O)]2 · 2H2O, where LH = 3-[1-(4-nitroimidazoyl)]propionic acid
  作者：David M.L. Goodgame、Christopher J. Page、David J. Williams、Ian J. Stratford

  DOI：10.1016/s0277-5387(00)83571-8

  日期：1992.1

  The preparations are reported of 3-[1-(4-nitroimidazoyl)]propionic acid, 3-[1-(2-methyl-4-nitroimidazoyl)]propionic acid and 3-[1-(2-nitroimidazoyl)]propionic acid, and also of some cobalt(II), copper(II), rhodium(II) and platinum(II) complexes with these ligands or with 3-[1-imidazoyl]propionic acid. The complexes were characterized by spectroscopic methods, and the compound [CuL2(H2O)]2.2H2O, where LH = 3-[1-(4-nitroimidazoyl)]propionic acid, was shown by X-ray diffraction to be dinuclear with each of the organic ligands bonded to two copper(II) ions via the carboxylate groups. Radiosensitization studies on [CuL2(H2O)]2.2H2O using hypoxic Chinese hamster V79 cells gave enhancement ratios similar to those for misonidazole, and significantly greater than those for typical, uncomplexed 4-nitroimidazoles.