三甲基-(2-硝基咪唑-1-基)硅烷 | 83107-48-6

• 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: 三甲基-(2-硝基咪唑-1-基)硅烷
• 英文名称: 1-(trimethylsilyl)-2-nitroimidazole
• 英文别名: 1-N-trimethylsilyl-2-nitroimidazole；trimethyl-(2-nitroimidazol-1-yl)silane
• CAS: 83107-48-6
• 化学式: C₆H₁₁N₃O₂Si
• 分子量: 185.258
• InChiKey: SXSKBECMUBMQGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3,4-三-O-乙酰基-alpha-D-阿拉伯吡喃糖基溴化物 、 三甲基-(2-硝基咪唑-1-基)硅烷 在 氰化汞 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以100%的产率得到1-(α-D-2,3,4-tri-O-acetylxylopyranosyl)-2-nitroimidazole
  参考文献：
  名称：

  An improved synthesis of α-AZA, α-AZP and α-AZG, the precursors to clinical markers of tissue hypoxia

  摘要：

  alpha-[I-123]-IAZA and alpha-[I-123]-IAZP are experimental diagnostic radiopharmaceuticals which have been used clinically to diagnose hypoxia in a number of pathologies, including cancer, peripheral vascular disease, rheumatoid arthritis and brain trauma. These nitroimidazole nucleosides are synthesized from the non-iodinated nucleosides AZA, AZP and AZG, respectively. Earlier methods report low chemical yields for the synthesis of these precursors. The modified procedures now reported provide nearly quantitative yields of these compounds, thereby substantially reducing the cost and effort of synthesis. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00099-5
• 作为产物：
  描述：

  2-硝基咪唑 、 六甲基二硅氮烷 在 吡啶 、 ammonium sulfate 作用下， 反应 1.5h， 生成 三甲基-(2-硝基咪唑-1-基)硅烷
  参考文献：
  名称：

  潜在的放射增敏剂。4. 2-硝基咪唑核苷。

  摘要：

  一系列2-硝基咪唑核苷类似物已被合成为潜在的放射增敏剂，以减少神经毒性并提高治疗功效。通过在氯化锡和氰化汞存在下缩合合成2-硝基咪唑的2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基和吡喃硫吡喃糖基类似物。这些酯的脱乙酰基在0℃下用甲醇钠进行。2-硝基咪唑的三甲基甲硅烷基衍生物与甲基2-脱氧-2-氯-4,7,8,9-四-O-乙酰基-N的缩合。在溴化汞的存在下获得了-乙酰基-α-D-神经氨酸。在有氧和低氧条件下，测试了这些试剂对中国仓鼠（V-79）细胞的体外细胞毒性和放射增敏作用。

  DOI：

  10.1021/jm00353a013

文献信息

• New azomycin acyclonucleoside. Synthesis and biodistribution of radiohalogenated analogues in tumor-bearing mice
  作者：Ahmad Hasan、Furn F. Knapp、Michael R. Kilbourn、Donald J. Buchsbaum

  DOI：10.1002/jhet.5570300528

  日期：1993.10

  The design, synthesis and biological activities of several acyclonucleoside analogues related to misoni-dazole are described. The hydroxy-5, bromo-6, iodo-7, and fluoro-8 derivatives of ethoxymethylazomycin and iodopropenyloxymethylazomycin (12) have been prepared. Alkylation of silylated azomycin with haloethoxy-methylene chloride gave the corresponding acyclonucleosides. Similarly, propargyloxymethylene

  描述了与米索尼达唑有关的几种无环核苷类似物的设计，合成和生物学活性。已经制备了乙氧基甲基azomycin和碘丙烯基氧基甲基azomycin的羟基-5，溴-6，碘-7和氟-8衍生物（12）。将甲硅烷基化的阿霉素用卤代乙氧基-二氯甲烷烷基化，得到相应的无环核苷。类似地，炔丙基氧基二氯甲烷产生炔丙基氧基甲基azomycin（10），其在加氢苯乙烯基化和随后的碘去锡基化之后产生碘丙烯基氧基甲基azomycin（12）。放射性标记的[ 125 I]或[ 18F]化合物是从相应的底物制备的。放射性标记类似物在小鼠中的生物分布结果表明，化合物7具有良好的肿瘤吸收（在1小时内注射剂量为2.0％/ g）。然而，血液和胃中的高放射性水平可能是由于体内脱碘或新陈代谢所致。在所有测试的化合物中，化合物[ 125 I] -12表现出最高的肿瘤吸收率（分别在1和4小时分别为4.8和3.6％注射剂量/ g）。与化合物〔
• METHOD FOR PRODUCING 2-NITROIMIDAZOLE DERIVATIVE
  申请人：Pola Pharma Inc.

  公开号：EP2128140B1

  公开（公告）日：2012-03-14
• 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.
• SRIVASTAVA, PREM C.;HASAN, AHMAD, NUCLEOSIDES AND NUCLEOTIDES, 9,(1990) N, C. 899-905
  作者：SRIVASTAVA, PREM C.、HASAN, AHMAD

  DOI：——

  日期：——
• AGRAWAL, KRISHNA, C.;SAKAGUCHI, MASAKAZU
  作者：AGRAWAL, KRISHNA, C.、SAKAGUCHI, MASAKAZU

  DOI：——

  日期：——