1-(2,3,5-tri-O-benzoyl-β-D-arabinofuranosyl)-2-nitroimidazole | 83416-41-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: 1-(2,3,5-tri-O-benzoyl-β-D-arabinofuranosyl)-2-nitroimidazole
• 英文别名: 1-(2',3',5'-tri-O-benzoyl-β-D-arabinofuranosyl)-2-nitroimidazole；1-(2,3,5-Tri-O-benzoyl-beta-D-arabinofuranosyl)-2-nitroimidazole；[(2R,3R,4S,5R)-3,4-dibenzoyloxy-5-(2-nitroimidazol-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 83416-41-5
• 化学式: C₂₉H₂₃N₃O₉
• 分子量: 557.516
• InChiKey: NDETXRJGONENPG-ZKGSSEMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-(2,3,5-tri-O-benzoyl-β-D-arabinofuranosyl)-2-nitroimidazole 在 sodium methylate 作用下， 反应 3.0h， 以54.6%的产率得到1-(β-D-arabinofuranosyl)-2-nitroimidazole
  参考文献：
  名称：

  Potential radiosensitizing agents. 6. 2-Nitroimidazole nucleosides: arabinofuranosyl and hexopyranosyl analogs

  摘要：

  New 2-nitroimidazole nucleosides have been synthesized as radiosensitizers of hypoxic mammalian cells in an attempt to reduce the neurotoxicity and to increase the therapeutic efficacy of this class of agents. The trimethylsilyl derivative of 2-nitroimidazole was condensed with 1-bromo-2,3,5-tri-O-benzoylarabinofuranose in the presence of mercuric cyanide to yield anomeric isomers of arabinofuranosides, which were separated by preparative thin-layer chromatography. Reaction of 2-deoxy-1,3,4,6-tetra-O-acetyl-D-glucose or 3,4,6-tri-O-acetyl-D-glucal with 2-nitroimidazole in the presence of an acid catalyst produced alpha and beta isomers of 2',3'-dideoxy-D-erythro-hex-2'-enopyranosides and an isomeric 3-substituted 1,2,3-trideoxy-D-erythro-hex-1-enopyranose. Hydrolysis of the esters was accomplished with sodium methoxide in methanol at 0 degrees C. The radiosensitizing efficacy of these agents was determined against Chinese hamster (V-79) cells in vitro. The 1-(2',3'-dideoxy-alpha-D-erythro-hex-2'-enopyranosyl)-2-nitroimidazole was the most active agent of this series and was found to be superior to misonidazole as a radiosensitizer.

  DOI：

  10.1021/jm00355a005
• 作为产物：
  描述：

  methyl tri-O-benzoyl-α-D-arabinofuranoside 在 氢溴酸 、 氰化汞 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 5.5h， 生成 1-(2,3,5-tri-O-benzoyl-β-D-arabinofuranosyl)-2-nitroimidazole
  参考文献：
  名称：

  碘化阿霉素核苷类组织缺氧新标志物的合成和放射性标记。

  摘要：

  已经合成了七种二代碘化阿霉素核苷类缺氧标记物，并在体外和体内测试了肿瘤细胞的缺氧标记活性。β-D-碘阿唑霉素半乳糖苷 (IAZG) 和 β-D-碘阿霉素木吡喃糖苷 (IAZXP) 表现出优于 IAZA 的缺氧标记特性，因为它们具有更高的水溶性、从荷瘤小鼠体内快速清除血浆的速度和最大肿瘤/血液 ( /B) 和肿瘤/肌肉 (T/M) 比率。我们对动物肿瘤模型的研究表明，通过闪烁扫描或平面成像确定的这些标志物的 T/B 或 T/M 比率可以预测肿瘤缺氧的相对程度和肿瘤的放射抗性。© 1997 约翰威利父子公司。

  DOI：

  10.1002/(sici)1099-1344(199707)39:7<541::aid-jlcr5>3.0.co;2-b

文献信息

• Novel compounds for hypoxic cell therapy and imaging
  申请人：Wiebe Leonard

  公开号：US20060270610A1

  公开（公告）日：2006-11-30

  The present invention provides for compounds suitable for therapeutic treatment of hypoxic tissues, particularly for application in radiotherapy, chemosensitization, radiosensitization. The present invention further provides for compounds suitable for radioimaging of hypoxic cells.

  本发明提供了适用于治疗低氧组织的化合物，特别适用于放疗、化疗增敏和放疗增敏的应用。本发明还提供了适用于低氧细胞放射性成像的化合物。
• Markers of tissue hypoxia
  申请人：Alberta Cancer Board

  公开号：US05401490A1

  公开（公告）日：1995-03-28

  Novel nucleosides are provided having at least one hydrogen or hydroxide substitutent replaced by a .gamma.-emitting halogen. Methods of preparation of these nucleosides are provided and also a novel non-invasive method for the detection and measurement of tissue hypoxia in mammals.

  提供了具有至少一个氢或氢氧基取代物被γ-放射性卤素取代的新型核苷。提供了这些核苷的制备方法，还提供了一种新颖的非侵入式方法，用于检测和测量哺乳动物组织缺氧。
• Nitroimidazole radiosensitizers for hypoxic tumor cells and compositions
  申请人：Research Corporation

  公开号：US04462992A1

  公开（公告）日：1984-07-31

  Compounds of the formula: ##STR1## wherein W is selected from the group consisting of ##STR2## Wherein Q is hydrogen or --CH.sub.2 OR.sup.1 ; Z is hydrogen or --OR.sup.1 ; n is 1 or 2; wherein R.sup.1 are the same or different radicals selected from the group consisting of hydrogen, and ##STR3## where R.sup.2 is lower alkyl, aryl, or aralkyl; wherein the bond at positions 2' and 3' of structure I may be single or double; or it may be a C-nucleoside attached at 3' position of the sugar; X and Y are the same or different selected from the group consisting of hydrogen, an electron withdrawing group, and a group wherein X and Y taken together form a 6-membered carbocylic aromatic ring, are useful as radiosensitizing agents during x-ray radiotherapy of tumor cells.

  公式为：##STR1## 其中W选自以下组合：##STR2## 其中Q为氢或--CH.sub.2 OR.sup.1；Z为氢或--OR.sup.1；n为1或2；其中R.sup.1为氢、##STR3##的相同或不同基团，其中R.sup.2为较低的烷基、芳香族或芳基烷基；结构I的2'和3'位置的键可以是单键或双键；或者可以是连接在糖的3'位置的C-核苷酸；X和Y选自以下组合：氢、电子提取基团和X和Y在一起形成6-成员环烷基芳香环的基团。这些化合物在肿瘤细胞的X射线放疗期间作为放射增敏剂是有用的。
• A One-Pot Synthesis of 1-α- And 1-β-D-Arabinofuranosyl-2-Nitroimidazoles: Synthons to the Markers of Tumor Hypoxia
  作者：Ebrahim Naimi、Piyush Kumar、Alexander McEwan、Leonard Wiebe

  DOI：10.1081/ncn-200055700

  日期：2005.3.1

  1-alpha- and 1-beta-D-Arabinofuranosyl-2-nitroimidazole (alpha-AZA and beta-AZ A) are synthons for a number of potential markers of tissue hypoxia. A one pot synthesis in which 2-nitroimidazole is coupled with a mixture of alpha-and beta-1-O-acetyl-2-3,5-tri-O-benzoyl-D-arabinofuranose in the presence of stannic chloride, followed by deprotection using ammonia/methanol, is described. Previously reported conditions for coupling 2-nitroimidazole to 1-alpha-bromoarabinofuranose protected by base-hydrolyzable groups afforded alpha-AZA almost exclusively.
• AGRAWAL, KRISHNA, C.;SAKAGUCHI, MASAKAZU
  作者：AGRAWAL, KRISHNA, C.、SAKAGUCHI, MASAKAZU

  DOI：——

  日期：——