1-benzyloxy-4-(3',5'-di-O-toluoyl-2'-deoxy-β-D-ribofuranosyl)benzene | 479582-42-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-benzyloxy-4-(3',5'-di-O-toluoyl-2'-deoxy-β-D-ribofuranosyl)benzene
• CAS: 479582-42-8
• 化学式: C₃₄H₃₂O₆
• 分子量: 536.624
• InChiKey: OKWRZPHCBSOCFT-YKILCQELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-benzyloxy-4-(3',5'-di-O-toluoyl-2'-deoxy-β-D-ribofuranosyl)benzene 在 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 1.5h， 以76%的产率得到1-benzyloxy-4-(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
• 作为产物：
  描述：

  magnesium,phenylmethoxybenzene,bromide 在 硫酸 、 苯磺酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 10.0h， 生成 1-benzyloxy-4-(3',5'-di-O-toluoyl-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