1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-{N-[6-(trifluoroacetylamino)-hexyl]-acrylamide}-uracil | 386747-72-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-{N-[6-(trifluoroacetylamino)-hexyl]-acrylamide}-uracil
• 英文别名: [(2S,5R)-5-[2,4-dioxo-5-[(E)-3-oxo-3-[6-[(2,2,2-trifluoroacetyl)amino]hexylamino]prop-1-enyl]pyrimidin-1-yl]-2,5-dihydrofuran-2-yl]methyl acetate
• CAS: 386747-72-4
• 化学式: C₂₂H₂₇F₃N₄O₇
• 分子量: 516.474
• InChiKey: OGDLYGKOMRXYRG-BZSJAIEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  36.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  148.59
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-{N-[6-(trifluoroacetylamino)-hexyl]-acrylamide}-uracil 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 25.0h， 生成 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-[N-(6-aminohexyl)acrylamide]-uracil
  参考文献：
  名称：

  SYNTHESIS OF 5-ALKENYLATED D4T ANALOGUES VIA THE Pd-CATALYZED CROSS-COUPLING REACTION

  摘要：

  The target compounds 5-[N-(6-amino-hexyl)-acrylamide]-2 ' ,3 ' -didehydro-2 ' ,3 ' -dideoxy-uridine (12) and 5-{N-[5-(methoxycarbonyl)-pentyl]acrylamide}-2 ' ,3 ' -didehydro-2',3 ' -dideoxy-uridine (15) were prepared by the palladium acetate-triphenylphosphine-catalyzed reaction of the 5 ' -O-acetyl-5-iodo-d4T analogue (3). These compounds 12 and 15 can be used to prepare nucleotide probes carrying fluorescent labels and were nevertheless screened for their anti-HIV activity. The biological data demonstrated that none of them were active against HIV-1.

  DOI：

  10.1081/ncn-100105902
• 作为产物：
  描述：

  1,6-己二胺 在 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 86.0h， 生成 1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-{N-[6-(trifluoroacetylamino)-hexyl]-acrylamide}-uracil
  参考文献：
  名称：

  SYNTHESIS OF 5-ALKENYLATED D4T ANALOGUES VIA THE Pd-CATALYZED CROSS-COUPLING REACTION

  摘要：

  The target compounds 5-[N-(6-amino-hexyl)-acrylamide]-2 ' ,3 ' -didehydro-2 ' ,3 ' -dideoxy-uridine (12) and 5-{N-[5-(methoxycarbonyl)-pentyl]acrylamide}-2 ' ,3 ' -didehydro-2',3 ' -dideoxy-uridine (15) were prepared by the palladium acetate-triphenylphosphine-catalyzed reaction of the 5 ' -O-acetyl-5-iodo-d4T analogue (3). These compounds 12 and 15 can be used to prepare nucleotide probes carrying fluorescent labels and were nevertheless screened for their anti-HIV activity. The biological data demonstrated that none of them were active against HIV-1.

  DOI：

  10.1081/ncn-100105902