1-hydroxy-2-(2'-deoxy-β-D-ribofuranosyl)benzene | 479582-28-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-hydroxy-2-(2'-deoxy-β-D-ribofuranosyl)benzene
• 英文别名: (2R,3S,5R)-2-(hydroxymethyl)-5-(2-hydroxyphenyl)oxolan-3-ol
• CAS: 479582-28-0
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: GQMYTXRJNFBXRU-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-hydroxy-2-(2'-deoxy-β-D-ribofuranosyl)benzene 在 磷酸三甲酯 、 1,8-双二甲氨基萘 、 三氯氧磷 、 三正丁胺 、 三丁基焦磷酸铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.02h， 生成 1-hydroxy-2-(2'-deoxy-β-D-ribofuranosyl)benzene 5'-triphosphate
  参考文献：
  名称：

  Syntheses and Structure−Activity Relationships of Nonnatural β-C-Nucleoside 5‘-Triphosphates Bearing an Aromatic Nucleobase with Phenolic Hydroxy Groups:  Inhibitory Activities against DNA Polymerases

  摘要：

  Five normatural beta-C-nucleoside 5'-triphosphates bearing a 3,4-dihydroxyphenyl (1TP), a 2-hydroxyphenyl (2TP), a 3-hydroxyphenyl (3TP), a 4-hydroxyphenyl (4TP), or a phenyl (5TP) group were synthesized, and their structure-activity relationships were examined for a series of DNA polymerase reactions in vitro under typical polymerase chain reaction conditions. We found that the 5'-triphosphates (1TP-5TP) are not incorporated into DNA strands but inhibit the DNA polymerase reactions in the presence of natural nucleoside 5'-triphosphates (dNTPs). 1TP having two phenolic hydroxy groups at the nucleobase moiety showed the most potent inhibitory effect against DNA synthesis by Ex Taq polymerase (IC50 = 30 muM). The competition assay indicated that 1TP and dNTPs are most likely to affect DNA polymerase reactions competitively. This finding may raise the appealing possibility that artificial nucleoside 5'-triphosphates having phenolic hydroxy groups could exhibit potent inhibitory activity against DNA-directed enzymatic reactions.

  DOI：

  10.1021/jm020193w
• 作为产物：
  描述：

  1-hydroxy-2-(3',5'-di-O-acetyl-2'-deoxy-β-D-ribofuranosyl)benzene 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以76%的产率得到1-hydroxy-2-(2'-deoxy-β-D-ribofuranosyl)benzene
  参考文献：
  名称：

  Syntheses and Structure−Activity Relationships of Nonnatural β-C-Nucleoside 5‘-Triphosphates Bearing an Aromatic Nucleobase with Phenolic Hydroxy Groups:  Inhibitory Activities against DNA Polymerases

  摘要：

  Five normatural beta-C-nucleoside 5'-triphosphates bearing a 3,4-dihydroxyphenyl (1TP), a 2-hydroxyphenyl (2TP), a 3-hydroxyphenyl (3TP), a 4-hydroxyphenyl (4TP), or a phenyl (5TP) group were synthesized, and their structure-activity relationships were examined for a series of DNA polymerase reactions in vitro under typical polymerase chain reaction conditions. We found that the 5'-triphosphates (1TP-5TP) are not incorporated into DNA strands but inhibit the DNA polymerase reactions in the presence of natural nucleoside 5'-triphosphates (dNTPs). 1TP having two phenolic hydroxy groups at the nucleobase moiety showed the most potent inhibitory effect against DNA synthesis by Ex Taq polymerase (IC50 = 30 muM). The competition assay indicated that 1TP and dNTPs are most likely to affect DNA polymerase reactions competitively. This finding may raise the appealing possibility that artificial nucleoside 5'-triphosphates having phenolic hydroxy groups could exhibit potent inhibitory activity against DNA-directed enzymatic reactions.

  DOI：

  10.1021/jm020193w

文献信息

• Syntheses and Structure−Activity Relationships of Nonnatural β-<i>C</i>-Nucleoside 5‘-Triphosphates Bearing an Aromatic Nucleobase with Phenolic Hydroxy Groups:  Inhibitory Activities against DNA Polymerases
  作者：Saeko Aketani、Kentaro Tanaka、Kaneyoshi Yamamoto、Akira Ishihama、Honghua Cao、Atsushi Tengeiji、Shuichi Hiraoka、Motoo Shiro、Mitsuhiko Shionoya

  DOI：10.1021/jm020193w

  日期：2002.12.1

  Five normatural beta-C-nucleoside 5'-triphosphates bearing a 3,4-dihydroxyphenyl (1TP), a 2-hydroxyphenyl (2TP), a 3-hydroxyphenyl (3TP), a 4-hydroxyphenyl (4TP), or a phenyl (5TP) group were synthesized, and their structure-activity relationships were examined for a series of DNA polymerase reactions in vitro under typical polymerase chain reaction conditions. We found that the 5'-triphosphates (1TP-5TP) are not incorporated into DNA strands but inhibit the DNA polymerase reactions in the presence of natural nucleoside 5'-triphosphates (dNTPs). 1TP having two phenolic hydroxy groups at the nucleobase moiety showed the most potent inhibitory effect against DNA synthesis by Ex Taq polymerase (IC50 = 30 muM). The competition assay indicated that 1TP and dNTPs are most likely to affect DNA polymerase reactions competitively. This finding may raise the appealing possibility that artificial nucleoside 5'-triphosphates having phenolic hydroxy groups could exhibit potent inhibitory activity against DNA-directed enzymatic reactions.