3-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2,4-dioxopyrimidin-5-yl]-N-[3-(2,6-dipyridin-2-ylpyridin-4-yl)sulfanylpropyl]propanamide | 175355-08-5

• 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: 3-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2,4-dioxopyrimidin-5-yl]-N-[3-(2,6-dipyridin-2-ylpyridin-4-yl)sulfanylpropyl]propanamide
• CAS: 175355-08-5
• 化学式: C₅₁H₅₀N₆O₈S
• 分子量: 907.059
• InChiKey: ODJNOFNPLAGNIH-PBQAQGAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  66
• 可旋转键数：
  19
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  200
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 3-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2,4-dioxopyrimidin-5-yl]-N-[3-(2,6-dipyridin-2-ylpyridin-4-yl)sulfanylpropyl]propanamide 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到3-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]-2,4-dioxopyrimidin-5-yl]-N-[3-(2,6-dipyridin-2-ylpyridin-4-yl)sulfanylpropyl]propanamide
  参考文献：
  名称：

  Building Blocks for Ribozyme Mimics:  Conjugates of Terpyridine and Bipyridine with Nucleosides

  摘要：

  The incorporation of the 2,2':6',2 ''-terpyridyl (terpy) complex of Cu(II) into a deoxyoligonucleotide has led to a functional mimic of ribozymes. The resulting mimic can cleave target RNA in a sequence-directed manner by a hydrolytic mechanism. Here we describe the synthesis and characterization of four modified nucleoside phosphoramidite reagents (7, 10, 14, and 18) that contain pendant 2,2'-bipyridine or terpy ligands. The ligands are attached either to the nucleobase (7, 10) or to the sugar (14, 18). Nucleobase modification was carried out at the C-5 position of 2'-deoxyuridine (dU). One route to sugar modification was performed by synthesis of 18, a 1'-functionalized analog of dU based on 1-[3-deoxy-beta-D-psicofuranosyl]uracil. Another route to sugar functionaliztion resulted in 14, a 2'-O-alkyl derivative of adenosine. These modified nucleosides are building blocks for ribozyme mimics. They are designed to deliver hydrolytically active metal complexes across either the major groove (7, 10) or the minor groove (14, 18) of an RNA/DNA duplex.

  DOI：

  10.1021/jo9518213
• 作为产物：
  描述：

  4'-(3-aminopropylsulfanyl)-2,2':6',2"-terpyridine 在 吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 生成 3-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2,4-dioxopyrimidin-5-yl]-N-[3-(2,6-dipyridin-2-ylpyridin-4-yl)sulfanylpropyl]propanamide
  参考文献：
  名称：

  Bashkin; Frolova; Sampath, Journal of the American Chemical Society, 1994, vol. 116, # 13, p. 5981 - 5982

  摘要：

  DOI：

文献信息

• Bashkin; Frolova; Sampath, Journal of the American Chemical Society, 1994, vol. 116, # 13, p. 5981 - 5982
  作者：Bashkin、Frolova、Sampath

  DOI：——

  日期：——
• Building Blocks for Ribozyme Mimics:  Conjugates of Terpyridine and Bipyridine with Nucleosides
  作者：James K. Bashkin、Jin Xie、Andrew T. Daniher、UmaShanker Sampath、Jeffrey L.-F. Kao

  DOI：10.1021/jo9518213

  日期：1996.1.1

  The incorporation of the 2,2':6',2 ''-terpyridyl (terpy) complex of Cu(II) into a deoxyoligonucleotide has led to a functional mimic of ribozymes. The resulting mimic can cleave target RNA in a sequence-directed manner by a hydrolytic mechanism. Here we describe the synthesis and characterization of four modified nucleoside phosphoramidite reagents (7, 10, 14, and 18) that contain pendant 2,2'-bipyridine or terpy ligands. The ligands are attached either to the nucleobase (7, 10) or to the sugar (14, 18). Nucleobase modification was carried out at the C-5 position of 2'-deoxyuridine (dU). One route to sugar modification was performed by synthesis of 18, a 1'-functionalized analog of dU based on 1-[3-deoxy-beta-D-psicofuranosyl]uracil. Another route to sugar functionaliztion resulted in 14, a 2'-O-alkyl derivative of adenosine. These modified nucleosides are building blocks for ribozyme mimics. They are designed to deliver hydrolytically active metal complexes across either the major groove (7, 10) or the minor groove (14, 18) of an RNA/DNA duplex.