N-[9-((1S,3R,4R,7S)-7-Benzyloxy-1-benzyloxymethyl-2,5-dioxa-bicyclo[2.2.1]hept-3-yl)-9H-purin-6-yl]-benzamide | 206055-66-5

• 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: N-[9-((1S,3R,4R,7S)-7-Benzyloxy-1-benzyloxymethyl-2,5-dioxa-bicyclo[2.2.1]hept-3-yl)-9H-purin-6-yl]-benzamide
• 英文别名: (1S,3R,4R,7S)-7-Benzyloxy-1-benzyloxymethyl-3-(6-N-benzoyladenin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane；N-[9-[(1S,3R,4R,7S)-7-phenylmethoxy-1-(phenylmethoxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl]purin-6-yl]benzamide
• CAS: 206055-66-5
• 化学式: C₃₂H₂₉N₅O₅
• 分子量: 563.613
• InChiKey: HIELKETXMJQMNI-KTIYVQITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-[9-((1S,3R,4R,7S)-7-Benzyloxy-1-benzyloxymethyl-2,5-dioxa-bicyclo[2.2.1]hept-3-yl)-9H-purin-6-yl]-benzamide 在 吡啶 、 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 N-[9-[(1R,4R,6R,7S)-4-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptan-6-yl]purin-6-yl]benzamide
  参考文献：
  名称：

  WO2020016782A5

  摘要：

  公开号：

  WO2020016782A5
• 作为产物：
  描述：

  N6-苯甲酰基腺嘌呤 在 N,O-双三甲硅基乙酰胺 、 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 为溶剂， 反应 22.0h， 生成 N-[9-((1S,3R,4R,7S)-7-Benzyloxy-1-benzyloxymethyl-2,5-dioxa-bicyclo[2.2.1]hept-3-yl)-9H-purin-6-yl]-benzamide
  参考文献：
  名称：

  WO2020016782A5

  摘要：

  公开号：

  WO2020016782A5

文献信息

• LNA (Locked Nucleic Acids): Synthesis of the adenine, cytosine, guanine, 5-methylcytosine, thymine and uracil bicyclonucleoside monomers, oligomerisation, and unprecedented nucleic acid recognition
  作者：Alexei A. Koshkin、Sanjay K. Singh、Poul Nielsen、Vivek K. Rajwanshi、Ravindra Kumar、Michael Meldgaard、Carl Erik Olsen、Jesper Wengel

  DOI：10.1016/s0040-4020(98)00094-5

  日期：1998.4

  LNA (Locked Nucleic Acids), consisting of 2′-O,4′-C-methylene bicyclonucleoside monomers, is efficiently synthesized and its nucleic acid recognition potential evaluated for six different nucleobases, namely adenine, cytosine, guanine, 5-methylcytosine, thymine and uracil. Unprecedented increases (+3 to +8 °C per modification) in the thermal stability of duplexes towards both DNA and RNA were obtained

  由2'- O，4'- C-亚甲基双环核苷单体组成的LNA（锁定核酸）被有效合成，并评估了其对六种不同核碱基（腺嘌呤，胞嘧啶，鸟嘌呤，5-甲基胞嘧啶，胸腺嘧啶）的核酸识别潜力和尿嘧啶。当评估部分或完全修饰的LNA的混合序列时，双链体对DNA和RNA的热稳定性出现了前所未有的提高（每个修饰+3至+8°C）。错配序列的研究表明，与相应的未修饰参考链相比，LNA遵循具有普遍提高的选择性的Watson-Crick碱基配对规则。
• Oligonucleotide analogues
  申请人：Wengel Jesper

  公开号：US20050287566A1

  公开（公告）日：2005-12-29

  The present invention relates to novel bicyclic and tricyclic nucleoside and nucleotide analogues as well as to oligonucleotides comprising such elements. The nucleotide analogues, LNAs (Locked Nucleoside Analogues), are able to provide valuable improvements to oligonucleotides with respect to affinity and specificity towards complementary RNA and DNA oligomers. The novel type of LNA modified oligonucleotides, as well as the LNAs as such, are useful in a wide range of diagnostic applications as well as therapeutic applications. Among these can be mentioned antisense applications, PCR applications, strand displacement oligomers, as substrates for nucleic acid polymerases, as nucleotide based drugs, etc. The present invention also relates to such applications.

  本发明涉及新型的双环和三环核苷酸和核苷酸类似物，以及包含这些元素的寡核苷酸。这些核苷酸类似物，即锁定核苷酸类似物（LNAs），能够为寡核苷酸提供与互补RNA和DNA寡聚物的亲和力和特异性方面的有价值的改进。这种新型的LNA修饰的寡核苷酸以及LNA本身在广泛的诊断应用和治疗应用中非常有用。其中包括反义应用、PCR应用、链置换寡聚物、作为核酸聚合酶的底物、作为基于核苷酸的药物等。本发明还涉及这些应用。
• OLIGONUCLEOTIDE ANALOGUES
  申请人：Wengel Jesper

  公开号：US20100279895A1

  公开（公告）日：2010-11-04

  The present invention relates to novel bicyclic and tricyclic nucleoside and nucleotide analogues as well as to oligonucleotides comprising such elements. The nucleotide analogues, LNAs (Locked Nucleoside Analogues), are able to provide valuable improvements to oligonucleotides with respect to affinity and specificity towards complementary RNA and DNA oligomers. The novel type of LNA modified oligonucleotides, as well as the LNAs as such, are useful in a wide range of diagnostic applications as well as therapeutic applications. Among these can be mentioned antisense applications, PCR applications, strand displacement oligomers, as substrates for nucleic acid polymerases, as nucleotide based drugs, etc. The present invention also relates to such applications.

  本发明涉及新型的双环和三环核苷酸和核苷酸类似物，以及包含这些元素的寡核苷酸。这些核苷酸类似物，即LNAs（锁定核苷酸类似物），能够为寡核苷酸提供与互补RNA和DNA寡聚物相比亲和力和特异性的有价值的改进。这种新型的LNA修饰的寡核苷酸以及LNAs本身在广泛的诊断应用和治疗应用中都有用途。其中可以提到反义应用、PCR应用、链位移寡聚物、作为核酸聚合酶底物、作为核苷酸基药物等。本发明还涉及这些应用。
• Oligonucleotide Analogues
  申请人：WENGEL Jesper

  公开号：US20110245327A1

  公开（公告）日：2011-10-06

  The present invention relates to novel bicyclic and tricyclic nucleoside and nucleotide analogues as well as to oligonucleotides comprising such elements. The nucleotide analogues, LNAs ( L ocked N ucleoside A nalogues), are able to provide valuable improvements to oligonucleotides with respect to affinity and specificity towards complementary RNA and DNA oligomers. The novel type of LNA modified oligonucleotides, as well as the LNAs as such, are useful in a wide range of diagnostic applications as well as therapeutic applications. Among these can be mentioned antisense applications, PCR applications, strand displacement oligomers, as substrates for nucleic acid polymerases, as nucleotide based drugs, etc. The present invention also relates to such applications.

  本发明涉及新型的双环和三环核苷酸和核苷酸类似物，以及包含这些元素的寡核苷酸。核苷酸类似物，即锁定核苷酸类似物（LNAs），能够为寡核苷酸提供有价值的改进，使其对互补的RNA和DNA寡聚体具有更高的亲和力和特异性。这种新型的LNA修饰的寡核苷酸以及LNAs本身在广泛的诊断应用和治疗应用中都很有用。其中包括反义应用、PCR应用、链置换寡聚体、作为核酸聚合酶的底物、作为基于核苷酸的药物等。本发明还涉及这些应用。
• Bi-cyclic nucleoside, nucleotide and oligonucleoide analogues
  申请人：Exiqon A/S

  公开号：EP1557424A1

  公开（公告）日：2005-07-27

  The present invention relates to novel bicyclic and tricyclic nucleoside analogues as well as to oligonucleotides comprising such elements. The nucleotide analogues, LNAs (Locked Nucleoside Analogues), are able to provide valuable improvements to oligonucleotides with respect to affinity and specificity towards complementary RNA and DNA oligomers. The novel type of LNA modified oligonucleotides, as well as the LNAs as such, are useful in a wide range of diagnostic applications as well as therapeutic applications. Among these can be mentioned antisense applications, PCR applications, strand displacement oligomers, as substrates for nucleic acid polymerises, as nucleotide based drugs, etc. The present invention also relates to such applications.

  本发明涉及新型双环和三环核苷类似物以及包含此类元素的寡核苷酸。这种核苷酸类似物 LNA（锁定核苷酸类似物）能够在对互补 RNA 和 DNA 寡聚体的亲和性和特异性方面对寡核苷酸进行有价值的改进。新型 LNA 修饰寡核苷酸以及 LNA 本身可用于广泛的诊断和治疗应用。其中包括反义应用、PCR 应用、链置换寡聚体、核酸聚合底物、核苷酸类药物等。本发明也涉及此类应用。