5-O-benzoyl-4-C-hydroxymethyl-1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranose | 327614-69-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-O-benzoyl-4-C-hydroxymethyl-1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranose
• 英文别名: 5-O-benzoyl-4-C-hydroxymethyl-2,3-O-isopropylidene-1-O-methyl-β-D-ribofuranose；5-O-benzoyl-4-C-hydroxymethyl-1-O-methyl-2,3-O-isopropylidene-β-D-ribo-furanose；Methyl 5-O-Benzoyl-4-C-hydroxymethyl-2,3-O-isopropylidene-b-D-ribofuranoside；[(3aS,4R,6R,6aR)-4-(hydroxymethyl)-6-methoxy-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]methyl benzoate
• CAS: 327614-69-7
• 化学式: C₁₇H₂₂O₇
• 分子量: 338.357
• InChiKey: NXDFPSJPNCUXHS-IARIHHJXSA-N

物化性质

• 沸点：
  450.2±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-O-benzoyl-4-C-hydroxymethyl-1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranose 在 4-二甲氨基吡啶 、 三(三甲基硅基)硅烷 、 硫酸 、 三氟乙酸 、 1,1'-偶氮(氰基环己烷) 作用下， 以 吡啶 、 水 、 溶剂黄146 、 甲苯 、 乙腈 为溶剂， 反应 18.5h， 生成 1-O-acetyl-2,3,5-tri-O-benzoyl-4-C-methyl-β-D-ribofuranose
  参考文献：
  名称：

  Synthesis and cytotoxicity of 4′-C- and 5′-C-substituted toyocamycins

  摘要：

  Toyocamycin and some analogues have shown potent antitumor activities; however, none of them could be used clinically primarily owing to their cytotoxicity to normal human cells. In order to overcome the weakness of these nucleoside analogues, substitution of a variety of modified sugars for the ribofuranose was explored in our laboratories with expectation that certain sugar-modified toyocamycin analogues may be selectively cytotoxic to cancer cells. In this article, we report synthesis and cytotoxicity of 4'-C- and T-C-substituted toyocamycins, which were prepared via the condensations of 4-C- and 5-C-substituted ribofuranose derivatives 11, 12, 13, 20, 21, and 26 with the silylated form of 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]py (27) and subsequent debromination and debenzoylation. When compared to the parent toyocamycin, all these analogues showed much lower cytotoxicity to human prostate cancer cells (HTB-81), mouse melanoma cancer cells (B16) as well as normal human fibroblasts. Compound le showed a significant cytotoxicity to the prostate cancer cells and a moderate selectivity. The results suggested that sugar modifications, especially those that may affect phosphorylation of nucleosides, could alter cytotoxicity profile significantly. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00221-2
• 作为产物：
  描述：

  ((3aS,6R,6aR)-6-甲氧基-2,2-二甲基四氢呋喃并[3,4-d][1,3]二氧杂环戊烯-4,4-二基)二甲醇 在 吡啶 作用下， 反应 19.0h， 生成 5-O-benzoyl-4-C-hydroxymethyl-1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranose
  参考文献：
  名称：

  フラビウィルス科ウィルス感染治療用の修飾２’および３’−ヌクレオシドプロドラッグ

  摘要：

  提供用于治疗黄病毒科病毒感染的1'、2'、3'或4'-分支核苷的2'和/或3'前药。 所述前药化合物或该化合物的制药可接受的盐，由式（I）表示。 该化合物可单独使用，也可与抗病毒药物如干扰素等联合使用或交替给药，用于预防或治疗黄病毒科病毒感染及其他相关状态。【R1-R3为H等；X1和X2为H或烷基等；Y1和Y3为烷基等】。【选择图】无

  公开号：

  JP2015205885A

文献信息

• Synthesis and Antiviral Evaluation of 4′-<i>C</i>-Azidomethyl-β-D-Ribofuranosyl Purine and Pyrimidine Nucleosides
  作者：Jean-François Griffon、Audrey Dumas、Richard Storer、Jean-Pierre Sommadossi、Gilles Gosselin

  DOI：10.1080/15257770903044531

  日期：2009.8.11

  the replication of RNA viruses, including hepatitis C virus (HCV), the hitherto unknown 4′-C-azidomethyl-β-D-ribofuranosyl nucleosides of the five naturally occurring nucleic acid bases have been synthesized and their antiviral properties examined. These 4′-C-branched nucleosides were stereospecifically prepared by glycosylation of purine and pyrimidine aglycons with a suitable peracylated 4-C-azido

  在寻找包括丙型肝炎病毒 (HCV) 在内的 RNA 病毒复制抑制剂的过程中，迄今为止未知的 5 种天然核酸碱基的 4'-C-叠氮甲基-β-D-呋喃核糖核苷已被合成并具有抗病毒作用。属性检查。这些 4'-C-分支的核苷是通过嘌呤和嘧啶苷元与合适的过酰化 4-C-叠氮甲基-D-戊呋喃糖进行糖基化，然后去除保护基团而立体定向制备的。测试了制备的化合物对几种病毒的活性，但它们没有显示出抗病毒作用。
• Methods and compositions for treating hepatitis C virus using 4'-modified nucleosides
  申请人：——

  公开号：US20040006007A1

  公开（公告）日：2004-01-08

  A compound, method and composition for treating a host infected with a hepatitis C viral comprising administering an effective hepatitis C treatment amount of a described 4′-disubstituted nucleoside or a pharmaceutically acceptable salt or prodrug thereof, is provided.

  提供一种用于治疗感染丙型肝炎病毒的宿主的化合物、方法和组合物，包括给予描述的4'-二取代核苷或其药用可接受的盐或前药的有效丙型肝炎治疗量。
• 2' and 3'-nucleoside prodrugs for treating Flaviviridae infections
  申请人：LaColla Paola

  公开号：US20070015905A1

  公开（公告）日：2007-01-18

  2′ and 3′-Prodrugs of 1′, 2′, 3′ or 4′-branched β-D or β-L nucleosides, or their pharmaceutically acceptable salts and derivatives are described, which are useful in the prevention and treatment of Flaviviridae infections and other related conditions. These modified nucleosides provide superior results against flaviviruses and pestiviruses, including hepatitis C virus and viruses generally that replicate through an RNA dependent RNA reverse transcriptase. Compounds, compositions, methods and uses are provided for the treatment of Flaviviridae infection, including HCV infection, that include the administration of an effective amount of the prodrugs of the present invention, or their pharmaceutically acceptable salts or derivatives. These drugs may optionally be administered in combination or alteration with further anti-viral agents to prevent or treat Flaviviridae infections and other related conditions.

  本文描述了1′、2′、3′或4′-支链β-D或β-L核苷的2′和3′-前药，或其药学上可接受的盐和衍生物，这些前药对于预防和治疗黄病毒科感染和其他相关疾病非常有用。这些改良核苷对黄病毒和猪瘟病毒，包括丙型肝炎病毒和一般通过RNA依赖性RNA逆转录酶复制的病毒，提供了优越的效果。本发明提供了化合物、组合物、方法和用于治疗黄病毒科感染，包括HCV感染的用于管理本发明的前药或其药学上可接受的盐或衍生物的有效量的用途。这些药物可以选择与其他抗病毒药物组合或交替使用，以预防或治疗黄病毒科感染和其他相关疾病。
• 一种核糖环修饰的mRNA帽类似物及其制备方法和应用
  申请人：江苏申基生物科技有限公司

  公开号：CN116143854A

  公开（公告）日：2023-05-23

  本发明提供了一种核糖环修饰的mRNA帽类似物及其制备方法和应用，该mRNA帽类似物结构中的五元糖环上与碳原子连接的氢原子选择性的独立的被OH、烷基、O‑烷基、CH2‑O‑烷基、CH2‑N‑烷基、CH2‑S‑烷基、卤素取代修饰，被修饰后的五元糖环分子构象优势，elF4E蛋白活性口袋结合能力更强，同时该结构不容易被脱帽酶识别，使得帽子结构更加稳定，最终表现出更好的mRNA翻译效果。
• US7138376B2
  申请人：——

  公开号：US7138376B2

  公开（公告）日：2006-11-21