1-(β-D-arabinofuranosyl)-2-nitroimidazole | 83416-42-6

• 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-(β-D-arabinofuranosyl)-2-nitroimidazole
• 英文别名: 1-β-D-arabinofuranosyl-2-nitroimidazole；1-(beta-D-Arabinofuranosyl)-2-nitroimidazole；(2R,3S,4S,5R)-2-(hydroxymethyl)-5-(2-nitroimidazol-1-yl)oxolane-3,4-diol
• CAS: 83416-42-6
• 化学式: C₈H₁₁N₃O₆
• 分子量: 245.192
• InChiKey: GEPYEWPQCQPUJN-MVIOUDGNSA-N

物化性质

• 熔点：
  160-162 °C
• 沸点：
  626.0±65.0 °C(Predicted)
• 密度：
  1.98±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(β-D-arabinofuranosyl)-2-nitroimidazole 在 吡啶 、 碘 、 三苯基膦 作用下， 反应 16.0h， 以38%的产率得到1-β-D-[5-deoxy-5-iodoarabinofuranosyl]-2-nitroimidazole
  参考文献：
  名称：

  Synthesis of 1-.BETA.-D-(5-Deoxy-5-iodoarabinofuranosyl)-2-nitroimidazole (.BETA.-IAZA): A Novel Marker of Tissue Hypoxia.

  摘要：

  本研究描述了1-α-<小>D-(5-脱氧-5-碘阿拉伯呋喃糖基)-2-硝基咪唑（IAZA）β-异构体的合成。放射性碘化IAZA（123I-IAZA）作为一种放射性药物，已被广泛用于诊断各种临床病理中的区域和/或局灶性组织缺氧。IAZA的β异构体--1-β-<小>D-(5-脱氧-5-碘阿拉伯呋喃糖基)-2-硝基咪唑（β-IAZA，1）是由1-β-<小>D-(核糖呋喃糖基)-2-硝基咪唑（AZR）通过非常规路线合成的、通过改变 C-2′ 位的构型，得到 1-β-<小>D-（阿拉伯呋喃糖基）-2-硝基咪唑（β-AZA，7）。对 β-AZA 的 5′-O-甲苯磺酰基-2′,3′-二-O-乙酰基前体 9 进行亲核碘化，然后进行脱保护，得到了 1，产率令人满意。还利用分子碘和三苯基膦从 7 合成了 β-IAZA (1)。

  DOI：

  10.1248/cpb.51.399
• 作为产物：
  描述：

  methyl tri-O-benzoyl-α-D-arabinofuranoside 在 硫酸 、 氨 、 氰化汞 、 四氯化锡 、 溶剂黄146 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 20.5h， 生成 1-(β-D-arabinofuranosyl)-2-nitroimidazole
  参考文献：
  名称：

  A One-Pot Synthesis of 1-α- And 1-β-D-Arabinofuranosyl-2-Nitroimidazoles: Synthons to the Markers of Tumor Hypoxia

  摘要：

  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.

  DOI：

  10.1081/ncn-200055700

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。
• 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。
• Potential radiosensitizing agents. 6. 2-Nitroimidazole nucleosides: arabinofuranosyl and hexopyranosyl analogs
  作者：Masakazu Sakaguchi、Cynthia A. Larroquette、Krishna C. Agrawal

  DOI：10.1021/jm00355a005

  日期：1983.1

  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.
• US4462992A
  申请人：——

  公开号：US4462992A

  公开（公告）日：1984-07-31
• US5401490A
  申请人：——

  公开号：US5401490A

  公开（公告）日：1995-03-28