1-(α-L-ribofuranosyl)cytosine | 179239-81-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(α-L-ribofuranosyl)cytosine
• 英文别名: 4-amino-1-α-L-ribofuranosyl-1H-pyrimidin-2-one；1-alpha-L-Ribofuranosylcytosine；4-amino-1-[(2R,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• CAS: 179239-81-7
• 化学式: C₉H₁₃N₃O₅
• 分子量: 243.219
• InChiKey: UHDGCWIWMRVCDJ-YDLFOAGRSA-N

物化性质

• 沸点：
  545.7±60.0 °C(Predicted)
• 密度：
  1.89±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(α-L-ribofuranosyl)cytosine 在 吡啶 、 咪唑 、 ammonium hydroxide 作用下， 反应 42.25h， 生成 4-N-benzoyl-1-(3-O-tert-butyldimethylsilyl-5-O-(4,4'-dimethoxytrityl)-α-L-ribofuranosyl)cytosine
  参考文献：
  名称：

  Synthesis and RNA-selective hybridization of α-l-ribo- and β-d-lyxo-configured oligonucleotides

  摘要：

  Three alpha-L-ribofuranosyl analogues of RNA nucleotides (alpha-L-RNA analogues) have been synthesized and incorporated into oligonucleotides using the phosphoramide approach on an automated DNA synthesizer. The 4'-C-hydroxymethyl-alpha-L-ribofuranosyl thymine monomer was furthermore synthesized. Relative to the unmodified duplexes, incorporation of a single a-L-RNA monomer into a DNA strand leads to reduced thermal stability of duplexes with DNA complements but unchanged thermal stability of duplexes with RNA complements, whereas incorporation of more than one alpha-L-RNA monomer lead to moderately decreased thermal stability also of duplexes with RNA complements. Efficient hybridization with an RNA complement and no melting transition with a DNA complement were observed with stereoregular chimeric oligonucleotides composed of a mixture of alpha-L-RNA and affinity enhancing alpha-L-LNA monomers (alpha-L-ribo-configured locked nucleic acid). Furthermore, duplexes formed between oligodeoxynucleotides containing an alpha-L-RNA monomer and complementary RNA were good substrates for Escherichia coli RNase H. RNA-selective hybridization was also achieved by the incorporation of 1-(4-C-hydroxymethyl-beta-D-lyxofuranosyl)thymine monomers into a DNA strand, whereas stable duplexes were formed with both complementary DNA and RNA when these monomers were incorporated into an RNA strand. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.007
• 作为产物：
  描述：

  L-核糖 在 劳森试剂 、 吡啶 、 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 1-(α-L-ribofuranosyl)cytosine
  参考文献：
  名称：

  Synthesis and RNA-selective hybridization of α-l-ribo- and β-d-lyxo-configured oligonucleotides

  摘要：

  Three alpha-L-ribofuranosyl analogues of RNA nucleotides (alpha-L-RNA analogues) have been synthesized and incorporated into oligonucleotides using the phosphoramide approach on an automated DNA synthesizer. The 4'-C-hydroxymethyl-alpha-L-ribofuranosyl thymine monomer was furthermore synthesized. Relative to the unmodified duplexes, incorporation of a single a-L-RNA monomer into a DNA strand leads to reduced thermal stability of duplexes with DNA complements but unchanged thermal stability of duplexes with RNA complements, whereas incorporation of more than one alpha-L-RNA monomer lead to moderately decreased thermal stability also of duplexes with RNA complements. Efficient hybridization with an RNA complement and no melting transition with a DNA complement were observed with stereoregular chimeric oligonucleotides composed of a mixture of alpha-L-RNA and affinity enhancing alpha-L-LNA monomers (alpha-L-ribo-configured locked nucleic acid). Furthermore, duplexes formed between oligodeoxynucleotides containing an alpha-L-RNA monomer and complementary RNA were good substrates for Escherichia coli RNase H. RNA-selective hybridization was also achieved by the incorporation of 1-(4-C-hydroxymethyl-beta-D-lyxofuranosyl)thymine monomers into a DNA strand, whereas stable duplexes were formed with both complementary DNA and RNA when these monomers were incorporated into an RNA strand. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.007

文献信息

• Macrocyclic compounds as inhibitors of viral replication
  申请人：Blatt M. Lawrence

  公开号：US20050267018A1

  公开（公告）日：2005-12-01

  The embodiments provide compounds of the general formulas I-XIX, as well as compositions, including pharmaceutical compositions, comprising a subject compound. The embodiments further provide treatment methods, including methods of treating flaviviral infection, including hepatitis C virus infection and methods of treating liver fibrosis, the methods generally involving administering to an individual in need thereof an effective amount of a subject compound or composition.

  该实施例提供了一般式I-XIX的化合物，以及包括药物组合在内的组合物，其中包括一种主体化合物。该实施例还提供了治疗方法，包括治疗黄病毒感染的方法，包括丙型肝炎病毒感染的方法和治疗肝纤维化的方法，这些方法通常涉及向需要的个体施用一种主体化合物或组合物的有效量。
• Meteorite-catalyzed intermolecular <i>trans</i>-glycosylation produces nucleosides under proton beam irradiation
  作者：Bruno Mattia Bizzarri、Angelica Fanelli、Michail Kapralov、Eugene Krasavin、Raffaele Saladino

  DOI：10.1039/d1ra02379a

  日期：——

  Di-glycosylated adenines act as glycosyl donors in the intermolecular trans-glycosylation of pyrimidine nucleobases under proton beam irradiation conditions. Formamide and chondrite meteorite NWA 1465 increased the yield and the selectivity of the reaction. The glycosyl transfer process was highly regioselective in yielding canonical N 1-pyrimidine nucleosides, the natural β-anomers prevailing in the

  在质子束照射条件下，二糖基化腺嘌呤在嘧啶核碱基的分子间反式糖基化中充当糖基供体。甲酰胺和球粒陨石 NWA 1465 提高了反应的产率和选择性。糖基转移过程在产生经典 N 1-嘧啶核苷方面具有高度区域选择性，这是在甲酰胺和 NWA 1465 存在下普遍存在的天然 β-异头物。这些数据突出了分子间反式糖基化在嘌呤和嘧啶的益生元形成中的可能作用核苷，避免出现独立的合成途径。
• L-ribofuranosyl nucleosides
  申请人：Genencor International, Inc.

  公开号：US05559101A1

  公开（公告）日：1996-09-24

  This invention relates to .alpha. and .beta. L-ribofuranosyl nucleosides, processes for their preparation, pharmaceutical compositions containing them, and methods of using them to treat various diseases in mammals.

  本发明涉及α和β L-核糖呋喃核苷，其制备过程，包含它们的制药组合物以及使用它们治疗哺乳动物的各种疾病的方法。
• Methods and compositions of treating a flaviviridae family viral infection
  申请人：Einav Shirit

  公开号：US20100015093A1

  公开（公告）日：2010-01-21

  Briefly described, embodiments of this disclosure include compounds, pharmaceutical compositions, methods of treating a host infected with a virus from the Flaviviridae family of viruses, methods of inhibiting HCV replication in a host, methods of inhibiting the binding of NS4B polypeptide to the 3′UTR of HCV negative strand RNA in a host, methods of treating liver fibrosis in a host, and the like.

  简要概述，本公开的实施例包括化合物、药物组合物、治疗感染黄病毒科病毒的宿主的方法、抑制宿主中HCV复制的方法、抑制NS4B多肽与HCV负链RNA的3′UTR结合的方法、治疗宿主肝纤维化的方法等。
• MACROCYCLIC COMPOUNDS AS INHIBITORS OF VIRAL REPLICATION
  申请人：BLATT LAWRENCE M.

  公开号：US20090286843A1

  公开（公告）日：2009-11-19

  The embodiments provide compounds of the general formulas I-XIX, as well as compositions, including pharmaceutical compositions, comprising a subject compound. The embodiments further provide treatment methods, including methods of treating flaviviral infection, including hepatitis C virus infection and methods of treating liver fibrosis, the methods generally involving administering to an individual in need thereof an effective amount of a subject compound or composition.

  该实施例提供了一般式I-XIX的化合物，以及包括药物组合物在内的组合物。该实施例还提供了治疗方法，包括治疗黄热病毒感染的方法，包括丙型肝炎病毒感染的方法和治疗肝纤维化的方法，通常涉及向需要治疗的个体施用所述化合物或组合物的有效量。