(S)-5-amino-6-cyano-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]imidazo[4,5-b]pyridine | 1187577-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: (S)-5-amino-6-cyano-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]imidazo[4,5-b]pyridine
• 英文别名: 5-amino-3-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]imidazo[4,5-b]pyridine-6-carbonitrile
• CAS: 1187577-38-3
• 化学式: C₁₃H₁₅N₅O₂
• 分子量: 273.294
• InChiKey: VMYDWHLVINJNGN-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  99
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-5-amino-6-cyano-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]imidazo[4,5-b]pyridine 在 吡啶 、 咪唑 、 四丁基氟化铵 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 113.5h， 生成 8-benzoylamino-3-[(2S)-3-(4,4'-dimethoxytrityloxy)-2-[[(2-cyanoethoxy)(N,N-diisopropylamino)phosphanyl]oxy]-propyl]imidazo[4',5':5,6]pyrido[2,3-d]pyrimidine
  参考文献：
  名称：

  Nucleic acid probe containing fluorescent tricyclic base-linked acyclonucleoside for detection of single nucleotide polymorphisms

  摘要：

  The development of a reliable and simple method for detecting single nucleotide polymorphisms (SNPs), common genetic variations in the human genome, is currently an important research area because SNPs are important for identifying disease-causing genes and for pharmacogenetic studies. Here, we developed a novel method for SNP detection. We designed and synthesized DNA probes containing a fluorescent tricyclic base-linked acyclonucleoside P. The type of nucleobases involved in the SNP sites in the DNA and RNA targets could be determined using four DNA probes containing P. Thus, this system would provide a novel and simple method for detecting SNPs in DNA and RNA targets. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.045
• 作为产物：
  描述：

  (9ci)-5-氨基-1H-咪唑并[4,5-b]吡啶-6-甲腈 、 (R)-(-)-对甲基苯磺酸-2,2-二甲基-1,3-二氧戊环基-4-甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 70.0h， 以54%的产率得到(S)-5-amino-6-cyano-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]imidazo[4,5-b]pyridine
  参考文献：
  名称：

  Nucleic acid probe containing fluorescent tricyclic base-linked acyclonucleoside for detection of single nucleotide polymorphisms

  摘要：

  The development of a reliable and simple method for detecting single nucleotide polymorphisms (SNPs), common genetic variations in the human genome, is currently an important research area because SNPs are important for identifying disease-causing genes and for pharmacogenetic studies. Here, we developed a novel method for SNP detection. We designed and synthesized DNA probes containing a fluorescent tricyclic base-linked acyclonucleoside P. The type of nucleobases involved in the SNP sites in the DNA and RNA targets could be determined using four DNA probes containing P. Thus, this system would provide a novel and simple method for detecting SNPs in DNA and RNA targets. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.045

文献信息

• RNA-SELECTIVE HYBRIDIZATION REAGENT AND USE OF THE SAME
  申请人：Ueno Yoshihito

  公开号：US20110033863A1

  公开（公告）日：2011-02-10

  Provided is a nucleoside derivative which has a high affinity for RNA. Use is made of a nucleoside derivative represented by either formula (1) or formula (2). (In formulae (1) and (2), Z represents a carbon atom or a nitrogen atom; R 1 represents a hydrogen atom or a hydroxyl-protecting group; and R 2 represents a hydrogen atom or a phosphodiester group).

  提供了一种对RNA具有高亲和力的核苷衍生物。使用的是由公式(1)或公式(2)所表示的核苷衍生物。（在公式(1)和(2)中，Z代表碳原子或氮原子；R1代表氢原子或羟基保护基；R2代表氢原子或磷酸二酯基团）。
• Development of a Probe Containing Novel Fluorescent Tricyclic-Nucleoside Analogs for Detecting Single Nucleotide Polymorphisms
  作者：Yoshihito Ueno、Ayako Moriya、Tokimitsu Ohki、Aya Hayai

  DOI：10.3987/com-14-13152

  日期：——

  Here we report the synthesis of nucleoside analogs containing several aryl groups at the 6-position of the fluorescent tricyclic base, 8-amino-3-(2,3-dihydroxypropyl)imidazo[4',5':5,6]pyrido[2,3-d]pyrimidine (1), to expand the fluorescence color range of single nucleotide polymorphism (SNP)-detecting probes. The identity of the RNA target bases could be determined using probes containing an analog with a phenyl group at the 6-position of 1.
• Fluorescence detection of single nucleotide polymorphisms using nucleic acid probe containing tricyclic base-linked acyclonucleoside
  作者：Mayumi Hattori、Tokimitsu Ohki、Emiko Yanase、Yoshihito Ueno

  DOI：10.1016/j.bmcl.2011.11.022

  日期：2012.1

  A reliable and simple method for detecting nucleobase mutations is very important clinically because sequence variations in human DNA cause genetic diseases and genetically influenced traits. A majority of sequence variations are attributed to single nucleotide polymorphisms (SNPs). Here, we developed a method for SNP detection using DNA probes that contained a fluorescent tricyclic base-linked acyclonucleoside N. The type of nucleobases involved in the SNP sites in an RNA target could be determined using four DNA probes containing N. Further, we found that the SNP in the RNA target could be detected by a visible color. Thus, this system would provide a novel and simple method for detecting SNPs in an RNA target. (C) 2011 Elsevier Ltd. All rights reserved.
• [EN] RNA-SELECTIVE HYBRIDIZATION REAGENT AND UTILIZATION OF THE SAME<br/>[FR] RÉACTIF D'HYBRIDATION SÉLECTIF DE L'ARN ET SON UTILISATION
  申请人：JAPAN SCIENCE & TECH AGENCY

  公开号：WO2009113580A1

  公开（公告）日：2009-09-17

  【課題】、ＲＮＡに対して高い親和性を有するヌクレオシド誘導体を提供する。 【解決手段】以下の式（１）及び式（２）のいずれかで表されるヌクレオシド誘導体を用いる。 （ただし、式（１）及び式（２）中、Ｚは、炭素原子又は窒素原子を表し、Ｒ1は、水素原子又は水酸基保護基を表し、Ｒ2は、水素原子又はホスホジエステル基を表す。）
• Nucleic acid probe containing fluorescent tricyclic base-linked acyclonucleoside for detection of single nucleotide polymorphisms
  作者：Kinji Furukawa、Mayumi Hattori、Tokimitsu Ohki、Yoshiaki Kitamura、Yukio Kitade、Yoshihito Ueno

  DOI：10.1016/j.bmc.2011.11.045

  日期：2012.1

  The development of a reliable and simple method for detecting single nucleotide polymorphisms (SNPs), common genetic variations in the human genome, is currently an important research area because SNPs are important for identifying disease-causing genes and for pharmacogenetic studies. Here, we developed a novel method for SNP detection. We designed and synthesized DNA probes containing a fluorescent tricyclic base-linked acyclonucleoside P. The type of nucleobases involved in the SNP sites in the DNA and RNA targets could be determined using four DNA probes containing P. Thus, this system would provide a novel and simple method for detecting SNPs in DNA and RNA targets. (C) 2011 Elsevier Ltd. All rights reserved.