methyl 5-deoxy-5-(2,4-dioxo-5-iodopyrimidin-1H-1-yl)-2,3-O-isopropylidene-β-D-ribofuranoside | 151576-00-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: methyl 5-deoxy-5-(2,4-dioxo-5-iodopyrimidin-1H-1-yl)-2,3-O-isopropylidene-β-D-ribofuranoside
• 英文别名: 1-[[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl]-5-iodopyrimidine-2,4-dione
• CAS: 151576-00-0
• 化学式: C₁₃H₁₇IN₂O₆
• 分子量: 424.192
• InChiKey: MJRIRDQUUDQZQE-TURQNECASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-deoxy-5-(2,4-dioxo-5-iodopyrimidin-1H-1-yl)-2,3-O-isopropylidene-β-D-ribofuranoside 在 palladium on activated charcoal 氢气 作用下， 生成 methyl 5-deoxy-5-(2,4-dioxopyrimidin-1H-1-yl)-2,3-O-isopropylidene-β-D-ribofuranoside
  参考文献：
  名称：

  Synthesis of "Reversed" and "Double Headed" Nucleosides

  摘要：

  The synthesis of several partially and fully deprotected ''reversed'' nucleosides are described starting from ''reversed'' 5-iodouracil-1-yl nucleoside 1. The preparation of a novel purine-purine and mixed purine-pyrimidine ''double headed'' nucleosides via ''reversed'' purine nucleoside 12 is also described.

  DOI：

  10.1080/15257779508012377
• 作为产物：
  描述：

  1-甲氧基-2,3-O-异亚丙基-5-O-对甲苯磺酰基-beta-D-呋喃核糖苷 、 5-碘尿嘧啶 在 sodium hydride 作用下， 生成 methyl 5-deoxy-5-(2,4-dioxo-5-iodopyrimidin-1H-1-yl)-2,3-O-isopropylidene-β-D-ribofuranoside
  参考文献：
  名称：

  A novel synthesis of “double headed” nucleosides “reversed” nucleosides

  摘要：

  The ''double headed' nucleosides 10, 11 and 13 bearing pyrimidine or purine bases attached on C-1 and C-5 positions of single ribose unit have been synthesized following a new synthetic strategy. The strategy rests on the introduction of the first nucleo base at C-5 position of the ribose unit giving 'reversed' nucleoside and the subsequent attachment of the second base at C-1 position of the ribose, by classical glycosylation reaction. This order of the base attachments gave much better yields on the ''double headed' nucleosides then previously known C-1 then C-5 order of attachments.

  DOI：

  10.1016/s0040-4039(00)74067-6

文献信息

• Synthesis and Biological Activity of Reversed Pyrimidine Nucleosides
  作者：Nataša Župančić、Željka Ban、Josipa Matić、Dijana Saftić、Ljubica Glavaš-Obrovac、Biserka Žinić

  DOI：10.5562/cca2531

  日期：——

  An efficient approach to reversed nucleosides which enables their synthesis in gram quantities is described. N-1'-Pyrimidine reversed nucleosides were prepared by treating of the sodium salt of pyrimidine bases with protected 5-tosyl ribose. Additionally, N-1',N-3'-disubstituted reversed nucleosides were isolated in the condensation reactions with the 5-halogen pyrimidines. Using the Sonogashira coupling of 5'-iodouracil reversed nucleoside with ethynyltrimethyl silane gave 5'-ethynyl derivative which was further transformed into 5'-acetyl reversed nucleoside. Biological activity of deprotected reversed nucleosides was validated on the panel of six human carcinoma cell lines (HeLa, MIAPaCa2, Hep2, NCI-H358, CaCo-2, and HT-29). 5'-Iodouracil derivative displayed moderate growth inhibition activity against human colon carcinoma (CaCo-2) cells.