2-amino-5-<(3S,4R,5S)-4,5-dihydroxycyclopent-1-en-3-ylaminomethyl>-4-(methylthio)pyrrolo<2,3-d>pyrimidine dihydrochloride | 102977-29-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-amino-5-<(3S,4R,5S)-4,5-dihydroxycyclopent-1-en-3-ylaminomethyl>-4-(methylthio)pyrrolo<2,3-d>pyrimidine dihydrochloride
• CAS: 102977-29-7
• 化学式: C₁₃H₁₇N₅O₂S*2ClH
• 分子量: 380.298
• InChiKey: IVEDVFRSQJRSEH-ANYFZDTESA-N

反应信息

• 作为产物：
  描述：

  5-[((3aR,4S,6aS)-2,2-Dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ylamino)-methyl]-4-methylsulfanyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamine 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 2-amino-5-<(3S,4R,5S)-4,5-dihydroxycyclopent-1-en-3-ylaminomethyl>-4-(methylthio)pyrrolo<2,3-d>pyrimidine dihydrochloride
  参考文献：
  名称：

  Queuine analogs. Their synthesis and inhibition of growth of mouse L5178Y cells in vitro

  摘要：

  A variety of analogues of queuine (7-[(3S,4R,5S)-4,5-dihydroxycyclopent-1-en-3-ylaminomethyl]- 7 -deazaguanine), i.e., those with 7-N-substituted aminomethyl side chains and those in which the oxygen function at the 6 position of the 7-deazaguanine ring was replaced by sulfur, were synthesized and tested for ability to act as substrates for tRNA-guanine transglycosylase and for inhibitory effects on growth of mouse L5178Y leukemic cells in vitro. Of the compounds tested, analogues with sulfur at the 6 position of the 7-deazaguanine ring in place of oxygen or with an N-o-hydroxyphenyl, N-m-hydroxyphenyl, or iodoacetyl group in the 7-aminomethyl side chain in place of the naturally occurring cyclopentene diol moiety markedly inhibited the growth of cells at concentrations of 1-10 micrograms/mL, although queuine itself had practically no effect at a concentration of 100 micrograms/mL.

  DOI：

  10.1021/jm00159a031