N-[3-(4,4'-dimethoxytrityloxymethyl)benzyl]-N'-[(6-tert-butyldimethylsilyloxymethylpyridine-2-yl)methyl]urea | 1311298-59-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-[3-(4,4'-dimethoxytrityloxymethyl)benzyl]-N'-[(6-tert-butyldimethylsilyloxymethylpyridine-2-yl)methyl]urea
• 英文别名: N-[3-(4,4'-dimethoxytrityloxymethyl)benzyl]-N'-{[6-(tert-butyldimethylsilyloxy)methylpyridin-2-yl]methyl}urea；1-[[3-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]phenyl]methyl]-3-[[6-[[tert-butyl(dimethyl)silyl]oxymethyl]pyridin-2-yl]methyl]urea
• CAS: 1311298-59-5
• 化学式: C₄₃H₅₁N₃O₅Si
• 分子量: 717.981
• InChiKey: ZNBCFVUKBPJFSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.13
• 重原子数：
  52
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  90.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[3-(4,4'-dimethoxytrityloxymethyl)benzyl]-N'-[(6-tert-butyldimethylsilyloxymethylpyridine-2-yl)methyl]urea 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以98%的产率得到N-[3-(4,4'-dimethoxytrityloxymethyl)benzyl]-N'-[(6-hydroxymethylpyridine-2-yl)methyl]urea
  参考文献：
  名称：

  AROMATIC COMPOUND, MODIFICATION CARRIER THAT USES SAME AND IS USED FOR SYNTHESIZING AN OLIGONUCLEOTIDE DERIVATIVE, OLIGONUCLEOTIDE DERIVATIVE, AND OLIGONUCLEOTIDE CONSTRUCT

  摘要：

  公开号：

  EP2511260B1
• 作为产物：
  描述：

  吡啶-2.6-二羧酸二甲酯 在 5%-palladium/activated carbon 锂硼氢 、 sodium azide 、 四溴化碳 、 氢气 、 sodium hydride 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 131.0h， 生成 N-[3-(4,4'-dimethoxytrityloxymethyl)benzyl]-N'-[(6-tert-butyldimethylsilyloxymethylpyridine-2-yl)methyl]urea
  参考文献：
  名称：

  AROMATIC COMPOUND, MODIFICATION CARRIER THAT USES SAME AND IS USED FOR SYNTHESIZING AN OLIGONUCLEOTIDE DERIVATIVE, OLIGONUCLEOTIDE DERIVATIVE, AND OLIGONUCLEOTIDE CONSTRUCT

  摘要：

  公开号：

  EP2511260B1

文献信息

• AROMATIC COMPOUND, MODIFICATION CARRIER THAT USES SAME AND IS USED FOR SYNTHESIZING AN OLIGONUCLEOTIDE DERIVATIVE, OLIGONUCLEOTIDE DERIVATIVE, AND OLIGONUCLEOTIDE CONSTRUCT
  申请人：Kitade Yukio

  公开号：US20120245341A1

  公开（公告）日：2012-09-27

  The present invention provides an oligonucleotide derivative that enables to easily synthesize an oligonucleotide derivative chemically modified at the 3′-end with two moieties each having a benzene or pyridine structure with a few steps, an aromatic compound serving as a precursor for preparing the modification carrier for synthesizing oligonucleotide derivative, and the oligonucleotide derivative and the oligonucleotide construct using the same, that is chemically modified at the 3′-end with two moieties each having a benzene or pyridine structure, and has good permeability through a cell membrane and excellent nuclease resistance. The modification carrier for synthesizing oligonucleotide derivative, comprising a unit and a carrier carrying the unit directly or via a linker, wherein the unit is represented by the formula (a): wherein, R 1 to R 6 each independently represent hydrogen or a substituent other than hydrogen; Z 1 and Z 2 each independently represent CH or nitrogen; and X represents oxygen or sulfur.

  本发明提供了一种寡核苷酸衍生物，使得可以通过几个步骤轻松地合成在3'-端带有两个苯或吡啶结构的化学修饰寡核苷酸衍生物，还提供了作为制备修饰载体的前体的芳香化合物，以及使用相同的化学修饰在3'-端带有两个苯或吡啶结构的寡核苷酸衍生物和寡核苷酸构建物，具有良好的细胞膜渗透性和出色的核酸酶抵抗性。用于合成寡核苷酸衍生物的修饰载体包括一个单元和一个携带该单元的载体，直接或通过连接剂携带该单元，其中该单元由式（a）表示：其中，R1到R6各自独立地表示氢或不是氢的取代基；Z1和Z2各自独立地表示CH或氮；X表示氧或硫。
• Oligonucleotide derivative comprising an aromatic compound
  申请人：Kitade Yukio

  公开号：US08633304B2

  公开（公告）日：2014-01-21

  The present invention provides an oligonucleotide derivative that enables to easily synthesize an oligonucleotide derivative chemically modified at the 3′-end with two moieties each having a benzene or pyridine structure with a few steps, an aromatic compound serving as a precursor for preparing the modification carrier for synthesizing oligonucleotide derivative, and the oligonucleotide derivative and the oligonucleotide construct using the same, that is chemically modified at the 3′-end with two moieties each having a benzene or pyridine structure, and has good permeability through a cell membrane and excellent nuclease resistance. The modification carrier for synthesizing oligonucleotide derivative, comprising a unit and a carrier carrying the unit directly or via a linker, wherein the unit is represented by the formula (a): wherein, R1 to R6 each independently represent hydrogen or a substituent other than hydrogen; Z1 and Z2 each independently represent CH or nitrogen; and X represents oxygen or sulfur.

  本发明提供了一种寡核苷酸衍生物，使得可以通过几个步骤轻松地合成化学修饰了两个苯或吡啶结构的基团的寡核苷酸衍生物，还提供了一种用于制备修饰载体以合成寡核苷酸衍生物的前体芳香化合物，以及使用相同的化学修饰了两个苯或吡啶结构的基团的寡核苷酸衍生物和寡核苷酸构建物，具有良好的细胞膜渗透性和优异的核酸酶抵抗性。用于合成寡核苷酸衍生物的修饰载体包括一个单元和一个携带该单元的载体，直接或通过连接剂携带该单元，其中该单元由式（a）表示：其中，R1到R6各自独立地表示氢或不是氢的取代基；Z1和Z2各自独立地表示CH或氮；X表示氧或硫。
• AROMATIC COMPOUND, MODIFICATION CARRIER THAT USES SAME AND IS USED FOR SYNTHESIZING AN OLIGONUCLEOTIDE DERIVATIVE, OLIGONUCLEOTIDE DERIVATIVE, AND OLIGONUCLEOTIDE CONSTRUCT
  申请人：Gifu University

  公开号：EP2511260B1

  公开（公告）日：2015-07-29
• Chemically modified siRNAs and miRNAs bearing urea/thiourea-bridged aromatic compounds at their 3′-end for RNAi therapy
  作者：Yoshiaki Kitamura、Yuki Masegi、Shunsuke Ogawa、Remi Nakashima、Yukihiro Akao、Yoshihito Ueno、Yukio Kitade

  DOI：10.1016/j.bmc.2013.05.046

  日期：2013.8

  We have developed chemically modified siRNAs and miRNAs bearing urea/thiourea-bridged aromatic compounds at their 3'-end for RNAi therapy. Chemically modified RNAs possessing urea/thiourea-bridged aromatic compounds instead of naturally occurring dinucleotides at the 3'-overhang region were easily prepared in good yields and were more resistant to nucleolytic hydrolysis than unmodified RNA. siRNAs containing urea or thiourea derivatives showed the desired knockdown effect. Furthermore, modified miR-143 duplexes carrying the urea/thiourea compounds in the 3'-end of each strand were able to inhibit the growth of human bladder cancer T24 cells. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.