1-[3,5-bis(hydroxymethyl)phenyl]-4-(dimethylamino)naphthalene | 1261237-69-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[3,5-bis(hydroxymethyl)phenyl]-4-(dimethylamino)naphthalene
• CAS: 1261237-69-7
• 化学式: C₂₀H₂₁NO₂
• 分子量: 307.392
• InChiKey: RXWOKPWPAQDUBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.7
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-[3,5-bis(hydroxymethyl)phenyl]-4-(dimethylamino)naphthalene 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 作用下， 反应 12.0h， 以44%的产率得到1-[3-(4,4'-dimethoxytrityloxymethyl)-5-(hydroxymethyl)phenyl]-4-(dimethylamino)naphthalene
  参考文献：
  名称：

  Biaryl modification of the 5′-terminus of one strand of a microRNA duplex induces strand specificity

  摘要：

  MicroRNAs (miRNAs) are single-stranded non-coding RNAs composed of 20-23 nucleotides. They are initially transcribed in the nucleus as pri-miRNAs. After processing, one strand from the miRNA duplex (miR-5p/miR-3p duplex) is loaded onto the RNA-induced silencing complex (RISC) to produce a functional, mature miRNA that inhibits the expression of multiple target genes. In the case of some miRNAs, both strands can be equally incorporated into the RISC as single strands, and both strands can function as mature miRNAs. Thus, a technique for selective expression of miR-5p and miR-3p strands is required to identify distinct targets of miRNAs. In this Letter, we report the synthesis and properties of miRNA duplexes carrying biaryl units at the 5'-terminus of one strand. We found that incorporation of biaryl units at the 5'-terminus of one strand of miRNA duplexes induced strand specificity in these duplexes. Further, we succeeded in identifying endogenous mRNA targets for each strand of the duplex by using the biaryl-modified miRNA duplexes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.077
• 作为产物：
  描述：

  1-[3,5-bis(tert-butyldimethylsilyloxymethyl)phenyl]-4-(dimethylamino)naphthalene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以66%的产率得到1-[3,5-bis(hydroxymethyl)phenyl]-4-(dimethylamino)naphthalene
  参考文献：
  名称：

  Biaryl modification of the 5′-terminus of one strand of a microRNA duplex induces strand specificity

  摘要：

  MicroRNAs (miRNAs) are single-stranded non-coding RNAs composed of 20-23 nucleotides. They are initially transcribed in the nucleus as pri-miRNAs. After processing, one strand from the miRNA duplex (miR-5p/miR-3p duplex) is loaded onto the RNA-induced silencing complex (RISC) to produce a functional, mature miRNA that inhibits the expression of multiple target genes. In the case of some miRNAs, both strands can be equally incorporated into the RISC as single strands, and both strands can function as mature miRNAs. Thus, a technique for selective expression of miR-5p and miR-3p strands is required to identify distinct targets of miRNAs. In this Letter, we report the synthesis and properties of miRNA duplexes carrying biaryl units at the 5'-terminus of one strand. We found that incorporation of biaryl units at the 5'-terminus of one strand of miRNA duplexes induced strand specificity in these duplexes. Further, we succeeded in identifying endogenous mRNA targets for each strand of the duplex by using the biaryl-modified miRNA duplexes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.077