2-(2-O,4-C-methylene-β-D-ribofuranosyl)-1-isoquinolone | 402859-75-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(2-O,4-C-methylene-β-D-ribofuranosyl)-1-isoquinolone
• 英文别名: 2-[(1S,3R,4R,7S)-7-hydroxy-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl]isoquinolin-1-one
• CAS: 402859-75-0
• 化学式: C₁₅H₁₅NO₅
• 分子量: 289.288
• InChiKey: GXZGCSCVZAWPMX-OSRDXIQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-O,4-C-methylene-β-D-ribofuranosyl)-1-isoquinolone 在 吡啶 、 二异丙基铵盐四氮唑 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 8.0h， 生成 2-[3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5-O-(4,4'-dimethoxytrityl)-2-O,4-C-methylene-β-D-ribofuranosyl]-1-isoquinolone
  参考文献：
  名称：

  Selective recognition of CG interruption by 2′,4′-BNA having 1-isoquinolone as a nucleobase in a pyrimidine motif triplex formation

  摘要：

  To develop a novel nucleoside analogue for the effective recognition of CG interruption in a homopurine-homopyrimidine tract of double-stranded DNA (dsDNA), we succeeded in the synthesis of a triplex-forming oligonucleotide (TFO) containing a novel 2',4'-BNA (Q(B)) bearing 1-isoquinolone as a nucleobase, and the triplex-forming ability and sequence-selectivity of the TFO (TFO-Q(B)) were examined. On melting temperature (T-m) measurements, it was found that the TFO-Q(B) formed a stable triplex DNA in a highly sequence-selective manner under near physiological conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00728-2
• 作为产物：
  描述：

  1-羟基异喹啉 在 palladium dihydroxide N,O-双三甲硅基乙酰胺 、 potassium carbonate 、 环己烯 作用下， 以 甲醇 、 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 13.0h， 生成 2-(2-O,4-C-methylene-β-D-ribofuranosyl)-1-isoquinolone
  参考文献：
  名称：

  Selective recognition of CG interruption by 2′,4′-BNA having 1-isoquinolone as a nucleobase in a pyrimidine motif triplex formation

  摘要：

  To develop a novel nucleoside analogue for the effective recognition of CG interruption in a homopurine-homopyrimidine tract of double-stranded DNA (dsDNA), we succeeded in the synthesis of a triplex-forming oligonucleotide (TFO) containing a novel 2',4'-BNA (Q(B)) bearing 1-isoquinolone as a nucleobase, and the triplex-forming ability and sequence-selectivity of the TFO (TFO-Q(B)) were examined. On melting temperature (T-m) measurements, it was found that the TFO-Q(B) formed a stable triplex DNA in a highly sequence-selective manner under near physiological conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00728-2

文献信息

• NOVEL NUCLEOSIDE ANALOGS AND OLIGONUCLEOTIDE DERIVATIVES CONTAINING THESE ANALOGS
  申请人：Imanishi, Takeshi

  公开号：EP1314734A1

  公开（公告）日：2003-05-28

  Nucleoside analogues expressed by the following general formula    where B represents an aromatic base having carbonyl oxygen at the 2-position, or a 2-hydroxyphenyl group, or oligonucleotide derivatives containing one or more of the nucleoside analogues are provided. The oligonucleotide derivatives are triplex-forming oligonucleotide derivatives which bind specifically to target double-stranded DNA with high affinity in the antigene method to form triplexes, and can thereby control and inhibit the expression of relevant genes efficiently, and which show high resistance to nucleases.

  提供了以下通式表达的核苷酸类似物：其中B代表具有2位羰基氧或2-羟基苯基基团的芳香碱基，或者含有一个或多个核苷酸类似物的寡核苷酸衍生物。这些寡核苷酸衍生物是三链体形成寡核苷酸衍生物，能够在抗原法中与目标双链DNA特异性结合，形成三链体，并能有效地控制和抑制相关基因的表达，同时表现出对核酸酶的高抗性。
• Novel nucleoside analogs and oligonucleotide derivatives containing these analogs
  申请人：——

  公开号：US20040192918A1

  公开（公告）日：2004-09-30

  Nucleoside analogues expressed by the following general formula 1 where B represents an aromatic base having carbonyl oxygen at the 2-position, or a 2-hydroxyphenyl group, or oligonucleotide derivatives containing one or more of the nucleoside analogues are provided. The oligonucleotide derivatives are triplex-forming oligonucleotide derivatives which bind specifically to target double-stranded DNA with high affinity in the antigene method to form triplexes, and can thereby control and inhibit the expression of relevant genes efficiently, and which show high resistance to nucleases.

  提供以下通式1所表示的核苷类似物，其中B代表具有2-位置上的羰基氧或2-羟基苯基基团的芳香基，或含有一种或多种核苷类似物的寡核苷酸衍生物。这些寡核苷酸衍生物是三链体形成寡核苷酸衍生物，通过抗基因方法与高亲和力地特异性结合目标双链DNA形成三链体，从而能够高效地控制和抑制相关基因的表达，并表现出高耐核酸酶的特性。
• US7053199B2
  申请人：——

  公开号：US7053199B2

  公开（公告）日：2006-05-30