7,9-二氢-9-beta-D-呋喃核糖基-1H-嘌呤-2,6,8(3H)-三酮 | 21082-30-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 7,9-二氢-9-beta-D-呋喃核糖基-1H-嘌呤-2,6,8(3H)-三酮
• 英文名称: 9-β-(D-ribofuranosyl)-1H-purine-2,6,8(3H,7H,9H)-trione
• 英文别名: 9-<β-D-Ribofuranosyl-(1)>-harnsaeure；3-Ribosyl-harnsaeure；9β-D-Ribofuranosyl-harnsaeure；9-β-D-ribofuranosyl uric acid；9-β-D-ribofuranosyl-7,9-dihydro-3H-purine-2,6,8-trione；9-(β-D-ribofuranosyl)purine-2,6,8(1H,3H,7H)-trione；9-ribofuranosyl-β-D-uric acid；9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,7-dihydropurine-2,6,8-trione
• CAS: 21082-30-4
• 化学式: C₁₀H₁₂N₄O₇
• 分子量: 300.228
• InChiKey: XRFDFDQNRIGZOW-UMMCILCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  161
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7,9-二氢-9-beta-D-呋喃核糖基-1H-嘌呤-2,6,8(3H)-三酮 生成 鸟苷
  参考文献：
  名称：

  Anti-HCV nucleoside derivatives

  摘要：

  本发明涉及新颖和已知的嘌呤和嘧啶核苷衍生物，已发现这些衍生物对丙型肝炎病毒（HCV）具有活性。本发明声明利用这些衍生物治疗HCV感染，以及本文所披露的新颖核苷衍生物。

  公开号：

  US20030008841A1
• 作为产物：
  描述：

  鸟苷 在 银 bromination reagent 、 氨 、 sodium acetate 、 亚硝酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 吡啶 、 水 、 溶剂黄146 、 丙酮 为溶剂， 生成 7,9-二氢-9-beta-D-呋喃核糖基-1H-嘌呤-2,6,8(3H)-三酮
  参考文献：
  名称：

  9-β-D-呋喃核糖基磺酸及其5'-单磷酸酯的新合成

  摘要：

  描述了从鸟苷开始并通过应用对硝基苯乙基保护基合成9-β-D-呋喃呋喃基葡萄糖酸（16）及其5'-单磷酸酯14的方法。

  DOI：

  10.1016/s0040-4039(00)98224-8

文献信息

• Nucleotides. Part XXVI.. A new synthesis of 9-(?-D-ribofuranosyl)uric acid and its 5?-monophosphate
  作者：Bernd S. Schulz、Wolfgang Pfleiderer

  DOI：10.1002/hlca.19870700126

  日期：1987.2.4

  Syntheses for 9-(β-D-ribofuranosyl)uric acid (16) and its 5′-monophosphate 14 have been achieved starting from guanosine and applying the 2-(p-nitrophenyl)ethyl group for protection of the aglycon moiety as well as the phosphate function. A more efficient and direct approach to 14 uses O6, O8-dibenzyl protection and phosphorylation by the Yoshikawa procedure. The various protected intermediates have

  9-（β-D-呋喃呋喃糖基）尿酸（16）及其5'-单磷酸酯14的合成已从鸟苷开始，并应用2-（对硝基苯基）乙基来保护糖苷配基以及磷酸盐功能。一种更有效的和直接的方法14层的用途Õ 6，直径：8二苄由保护和磷酸化吉川过程。各种受保护的中间体已通过光谱学方法和元素分析进行​​了表征。
• Oxidation of 9-β-d-ribofuranosyl uric acid by one-electron oxidants versus singlet oxygen and its implications for the oxidation of 8-oxo-7,8-dihydroguanosine
  作者：Khiem V. Nguyen、James G. Muller、Cynthia J. Burrows

  DOI：10.1016/j.tetlet.2010.11.123

  日期：2011.4

  Uric acid, a cellular antioxidant, undergoes oxidation in the presence of one-electron oxidants as well as singlet oxygen. In the present work, the oxidation pathways and products formed from oxidation of the uric acid nucleoside are compared to the more commonly studied uric acid free base. A wider distribution of products, including allantoin, urea, caffolide, and 5-carboxamido-5-hydroxyhydantoin nucleosides, are formed when the N9 position of uric acid is glycosylated. The oxidation pathways share some features in common with the oxidation of 8-oxo-7,8-dihydroguanosine, but the additional spectrum of products implies that the combination of oxidative and deaminative damage to guanosine may lead to a more complex set of DNA lesions than originally described. (C) 2010 Elsevier Ltd. All rights reserved.
• Purine and 8-substituted purine arabinofuranosyl and ribofuranosyl nucleoside derivatives as potential inducers of the differentiation of the Friend erythroleukemia
  作者：Tai Shun Lin、Jia Chong Cheng、Kimiko Ishiguro、Alan C. Sartorelli

  DOI：10.1021/jm00148a018

  日期：1985.10

  Several antimetabolites have been demonstrated to have the capacity to initiate differentiation in vitro of a variety of leukemic cell lines. To explore the structural requirements for this activity, a series of purine and 8-substituted purine arabinofuranosyl and ribofuranosyl nucleoside derivatives were synthesized and tested as inducers of the differentiation of Friend murine erythroleukemia cells. 9-(beta-D-Arabinofuranosyl)hypoxanthine and 6-(hydroxyamino)-9-(beta-D-arabinofuranosyl)purine were effective inducers of maturation, producing 82% and 74% benzidine-positive cells, a measure of the number of cells synthesizing hemoglobin. 6-Mercapto-9-(beta-D-ribofuranosyl)purine and 6-(methylmercapto)-9-(beta-D-ribofuranosyl)purine and their corresponding beta-D-arabinofuranosyl derivatives were also effective initiators of maturation, causing approximately 50% of the cell population to assume a differentiated phenotype.
• Pathway Analysis of Cell Culture Phenotypes and Uses Thereof
  申请人：Melville Mark

  公开号：US20090186358A1

  公开（公告）日：2009-07-23

  The present invention provides methods for systematically identifying genes, proteins and/or related pathways that regulate or indicative of cell phenotypes. The present invention further provides methods for manipulating the identified genes, proteins and/or pathways to engineer improved cell lines and/or to evaluate or select cell lines with desirable phenotypes.