1-methylxanthosine | 23392-10-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 1-methylxanthosine
• 英文别名: 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-methyl-3H-purine-2,6-dione
• CAS: 23392-10-1
• 化学式: C₁₁H₁₄N₄O₆
• 分子量: 298.255
• InChiKey: SOBHTUPJYFGBBX-KQYNXXCUSA-N

物化性质

• 密度：
  2.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  137
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-甲基鸟酐 在 sodium nitrite 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 60.0h， 以18%的产率得到1-methylxanthosine
  参考文献：
  名称：

  一系列1-甲基异鸟苷类似物的合成和药理评价。

  摘要：

  在肌肉松弛剂，心血管，抗炎和抗过敏试验中，评估了具有药理活性的海洋天然产物1-甲基异鸟苷（1）的一系列类似物的生物活性。在1位上的修饰分别产生乙基，正丁基，正辛基和苯基衍生物3-6。在8位的取代提供了溴，肼和氨基化合物9-11。在5'位的修饰产生了脱氧，碘和磷酸盐衍生物15、13和16，以及环状3'，5'-磷酸盐17。C-核苷类似物19的合成由β完成-D-呋喃核糖基羧酰亚胺酯20。无环类似物29和β-D-阿拉伯呋喃糖基衍生物35都是通过异氰酸甲酯与适当保护的氨基氰咪唑前体28和32反应合成的。1-甲基黄嘌呤（12），异鸟苷（7）和2-甲氧基腺苷（18）。也被合成。在高达100 mg / kg po的剂量下，5'-磷酸16，环状3'，5'-磷酸17和O-甲基化的类似物2-甲氧基腺苷18在产生肌肉松弛和体温过低方面具有活性。这些化合物具有抗过敏活性，并且与1-乙基（3）和1-正丁基（4）类似物

  DOI：

  10.1021/jm00140a007

文献信息

• CPG-like nucleic acids and methods of use thereof
  申请人：Coley Pharmaceutical GmbH

  公开号：EP1985702A2

  公开（公告）日：2008-10-29

  Immunostimulatory compositions described as CpG-like nucleic acids are provided, including nucleic acids having immunostimulatory characteristics of CpG nucleic acid, despite certain substitutions of C, G, or C and G of the CpG dinucleotide. The substitutions can include, among others, exchange of methylated C for C, inosine for G, and ZpY for CpG, where Z is Cytosine or dSpacer and Y is inosine, 2-aminopurine, nebularine, or dSpacer. Also provided are methods for inducing an immune response in a subject using the CpG-like nucleic acids. The methods are useful in the treatment of a subject that has or is at risk of developing an infectious disease, allergy, asthma, cancer, anemia, thrombocytopenia, or nutropenia.

  提供了被描述为 CpG 样核酸的免疫刺激组合物，包括具有 CpG 核酸免疫刺激特性的核酸，尽管 CpG 二核苷酸的 C、G 或 C 和 G 有某些替换。除其他外，这些取代可包括将甲基化的 C 换成 C，将肌苷换成 G，将 ZpY 换成 CpG，其中 Z 是胞嘧啶或 dSpacer，Y 是肌苷、2-氨基嘌呤、奈伯碱或 dSpacer。还提供了使用 CpG 样核酸诱导受试者免疫应答的方法。这些方法可用于治疗患有传染病、过敏症、哮喘、癌症、贫血、血小板减少症或营养不良症的受试者。
• High-Throughput Five Minute Microwave Accelerated Glycosylation Approach to the Synthesis of Nucleoside Libraries
  作者：Brett C. Bookser、Nicholas B. Raffaele

  DOI：10.1021/jo061885l

  日期：2007.1.1

  [GRAPHICS]The Vorbruggen glycosylation reaction was adapted into a one-step 5 min/130 degrees C microwave assisted reaction. Triethanolamine in acetontrile containing 2% water was determined to be optimal for the neutralization of trimethylsilyl triflate allowing for direct MPLC purification of the reaction mixture. When coupled with a NH3/methanol deprotection reaction, a high-throughput method of nucleoside library synthesis was enabled. The method was demonstrated by examining the ribosylation of 48 nitrogen containing heteroaromatic bases that included 25 purines, four pyrazolopyrimidines, two 8-azapurines, one 2-azapurine, two imidazopyridines, two benzimidazoles, three imidazoles, three 1,2,4-triazoles, two pyrimidines, two 3-deazapyrimidines, one quinazolinedione, and one alloxazine. Of these, 32 yielded single regioisomer products, and six resulted in separable mixtures. Seven examples provided inseparable regioisomer mixtures of -two to three compounds (16 nucleosides), and three examples failed to yield isolable products. For the 45 single isomers isolated, the average two-step overall yield +/- SD was 26 +/- 16%, and the average purity +/- SD was 95 +/- 6%. A total of 58 different nucleosides were prepared of which 15 had not previously been accessed directly from glycosylation/deprotection of a readily available base.
• Synthesis and pharmacological evaluation of a series of analogs of 1-methylisoguanosine
  作者：Robert T. Bartlett、Alan F. Cook、Michael J. Holman、Warren W. McComas、Eugene F. Nowoswait、Mohindar S. Poonian、Judy A. Baird-Lambert、Brian A. Baldo、John F. Marwood

  DOI：10.1021/jm00140a007

  日期：1981.8

  Modification at the 5' position yielded the deoxy, iodo, and phosphate derivatives 15, 13, and 16, as well as the cyclic 3',5'-phosphate 17. The synthesis of the C-nucleoside analogue 19 was achieved from the beta-D-ribofuranosylcarboximidic ester 20. The acyclic analogue 29 and the beta-D-arabinofuranosyl derivative 35 were both synthesized by reaction of methyl isocyanate with the appropriately protected

  在肌肉松弛剂，心血管，抗炎和抗过敏试验中，评估了具有药理活性的海洋天然产物1-甲基异鸟苷（1）的一系列类似物的生物活性。在1位上的修饰分别产生乙基，正丁基，正辛基和苯基衍生物3-6。在8位的取代提供了溴，肼和氨基化合物9-11。在5'位的修饰产生了脱氧，碘和磷酸盐衍生物15、13和16，以及环状3'，5'-磷酸盐17。C-核苷类似物19的合成由β完成-D-呋喃核糖基羧酰亚胺酯20。无环类似物29和β-D-阿拉伯呋喃糖基衍生物35都是通过异氰酸甲酯与适当保护的氨基氰咪唑前体28和32反应合成的。1-甲基黄嘌呤（12），异鸟苷（7）和2-甲氧基腺苷（18）。也被合成。在高达100 mg / kg po的剂量下，5'-磷酸16，环状3'，5'-磷酸17和O-甲基化的类似物2-甲氧基腺苷18在产生肌肉松弛和体温过低方面具有活性。这些化合物具有抗过敏活性，并且与1-乙基（3）和1-正丁基（4）类似物