2-amino-5-<1-(3,5-diiodo-4-hydroxyphenyl)-1-<((iminomethyl)amino)methyl>>pyrrolo<2,3-d>pyrimidin-4-one | 86694-44-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 2-amino-5-<1-(3,5-diiodo-4-hydroxyphenyl)-1-<((iminomethyl)amino)methyl>>pyrrolo<2,3-d>pyrimidin-4-one
• 英文别名: N'-[(2-amino-4-oxo-3,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)methyl]-4-hydroxy-3,5-diiodobenzenecarboximidamide
• CAS: 86694-44-2
• 化学式: C₁₄H₁₂I₂N₆O₂
• 分子量: 550.097
• InChiKey: TYWIYYHQSSDZGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  142
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-aminomethyl-7-deazaguanine dihydrochloride 、 methyl 3,5-diiodo-4-hydroxybenzimidate hydrochloride 在 sodium borate buffer 作用下， 以 甲醇 为溶剂， 反应 65.0h， 以133 mg的产率得到2-amino-5-<1-(3,5-diiodo-4-hydroxyphenyl)-1-<((iminomethyl)amino)methyl>>pyrrolo<2,3-d>pyrimidin-4-one
  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

文献信息

• Queuine analogs. Their synthesis and inhibition of growth of mouse L5178Y cells in vitro
  作者：Hiroshi Akimoto、Hiroaki Nomura、Mitsuzi Yoshida、Nobuko Shindo-Okada、Akio Hoshi、Susumu Nishimura

  DOI：10.1021/jm00159a031

  日期：1986.9

  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.