1-(3'-azido-3'-deoxy-β-D-ribofuranosyl)nicotinamide-5'-(butyl phosphate) | 1355216-14-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡啶核苷酸
• 英文名称: 1-(3'-azido-3'-deoxy-β-D-ribofuranosyl)nicotinamide-5'-(butyl phosphate)
• 英文别名: [(2S,3S,4R,5R)-3-azido-5-(3-carbamoylpyridin-1-ium-1-yl)-4-hydroxyoxolan-2-yl]methyl butyl phosphate
• CAS: 1355216-14-6
• 化学式: C₁₅H₂₂N₅O₇P
• 分子量: 415.343
• InChiKey: ZQIAMRXAQDUNTB-RGCMKSIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  烟酰胺 在 磷酸三甲酯 、 三氟甲磺酸三甲基硅酯 、 六甲基二硅氮烷 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 8.08h， 生成 1-(3'-azido-3'-deoxy-β-D-ribofuranosyl)nicotinamide-5'-(butyl phosphate)
  参考文献：
  名称：

  Studies on the Synthesis of Nicotinamide Nucleoside and Nucleotide Analogues and Their Inhibitions towards CD38 NADase

  摘要：

  Nicotinamide adenine dinucleotide (NAD) analogues inhibit the NADase activity of CD38. In the current study, efficient protocols for the synthesis of substituted-nicotinamide nucleosides and nucleotides were developed. The one-pot phosphorylation esterification strategy provides a convenient way of obtaining nicotinamide nucleoside phosphodiesters from the corresponding nucleosides. Structure activity relationship information revealed that replacement of 3'-hydroxy group with F or N-3 led to the considerably decrease of activity as compared with ara-F NMN. Phosphodiesterification of nicotinamide nucleosides lowers their inhibitory activities in some extent.

  DOI：

  10.3987/com-11-12361

文献信息

• Studies on the Synthesis of Nicotinamide Nucleoside and Nucleotide Analogues and Their Inhibitions towards CD38 NADase
  作者：Liangren Zhang、Anna Ka Yee Kwong、Zhenjun Yang、Zhe Chen、Hon Cheung Lee、Lihe Zhang

  DOI：10.3987/com-11-12361

  日期：——

  Nicotinamide adenine dinucleotide (NAD) analogues inhibit the NADase activity of CD38. In the current study, efficient protocols for the synthesis of substituted-nicotinamide nucleosides and nucleotides were developed. The one-pot phosphorylation esterification strategy provides a convenient way of obtaining nicotinamide nucleoside phosphodiesters from the corresponding nucleosides. Structure activity relationship information revealed that replacement of 3'-hydroxy group with F or N-3 led to the considerably decrease of activity as compared with ara-F NMN. Phosphodiesterification of nicotinamide nucleosides lowers their inhibitory activities in some extent.