1-(β-D-Ribofuranosyl)imidazol-4,5-dicarboxamid | 66678-51-1

• 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-Ribofuranosyl)imidazol-4,5-dicarboxamid
• 英文别名: 1-β-D-ribofuranosyl-1H-imidazole-4,5-dicarboxylic acid diamide；1-β-D-Ribofuranosyl-1H-imidazol-4,5-dicarbonsaeure-diamid；1-β-D-ribofuranosyl-imidazole-4,5-dicarboxamide；1-(β-D-Ribofuranosyl)-imidazol-4,5-dicarboxamid；1-beta-D-ribofuranosyl-imidazole-4,5-dicarboxamide；1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4,5-dicarboxamide
• CAS: 66678-51-1
• 化学式: C₁₀H₁₄N₄O₆
• 分子量: 286.244
• InChiKey: NLRZTUDUQPHELG-KAFVXXCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  174
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(β-D-Ribofuranosyl)imidazol-4,5-dicarboxamid 生成 1-Desoxy-1-(4,5-dicarbamoyl-imidazol-1-yl)-β-D-ribofuranuronsaeure
  参考文献：
  名称：

  FISCHER, U.;WYSS, P. -C.

  摘要：

  DOI：
• 作为产物：
  描述：

  4,5-二甲酰胺咪唑 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 16.08h， 生成 1-(β-D-Ribofuranosyl)imidazol-4,5-dicarboxamid
  参考文献：
  名称：

  High-Throughput Five Minute Microwave Accelerated Glycosylation Approach to the Synthesis of Nucleoside Libraries

  摘要：

  [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.

  DOI：

  10.1021/jo061885l

文献信息

• Ribofuranosyl-imidazole derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US04115641A1

  公开（公告）日：1978-09-19

  Ribofuranoysl-imidazole derivatives of the formula ##STR1## wherein R, X, Y and Z have one of the meanings set forth hereinafter, are described. The ribofuranosyl-imidazole derivatives have cardiac and circulatory-dynamic properties and are useful in the treatment of angina pectoris.

  描述了具有以下含义的化学式的核糖嘌呤-咪唑衍生物：##STR1## 这些核糖嘌呤-咪唑衍生物具有心脏和循环动力学特性，并可用于治疗心绞痛。
• Monocyclic L-nucleosides, analogs and uses thereof
  申请人：ICN Pharmaceuticals, Inc.

  公开号：EP1254911A1

  公开（公告）日：2002-11-06

  Novel monocyclic L- nucleoside compounds have general formula (I). Embodiments of these compounds are contemplated to be useful in treating a wide variety of diseases including infections, infestations, neoplasms, and autoimmune diseases. Viewed in terms of mechanism, embodiments of the novel compounds show immunomodulatory activity, and are expected to be useful in modulating the cytokine pattern, including modulation of Th 1 and Th 2 response.

  新型单环L-核苷化合物的一般化学式为（I）。这些化合物的实施形式被认为在治疗包括感染、寄生虫感染、肿瘤和自身免疫性疾病在内的各种疾病中是有用的。从机制上看，这些新型化合物的实施形式显示出免疫调节活性，并有望在调节细胞因子模式方面发挥作用，包括调节Th1和Th2反应。
• Howard et al., Journal of the Chemical Society, 1949, p. 232,233
  作者：Howard et al.

  DOI：——

  日期：——
• FISCHER, U.;WYSS, P. -C.
  作者：FISCHER, U.、WYSS, P. -C.

  DOI：——

  日期：——
• US4115641A
  申请人：——

  公开号：US4115641A

  公开（公告）日：1978-09-19