1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-{N-[6-(trifluoroacetylamino)-hexyl]-acrylamide}-uracil | 386747-74-6

• 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-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-{N-[6-(trifluoroacetylamino)-hexyl]-acrylamide}-uracil
• 英文别名: (E)-3-[1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-2,4-dioxo-pyrimidin-5-yl]-N-[6-[(2,2,2-trifluoroacetyl)amino]hexyl]prop-2-enamide；(E)-3-[1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-2,4-dioxopyrimidin-5-yl]-N-[6-[(2,2,2-trifluoroacetyl)amino]hexyl]prop-2-enamide
• CAS: 386747-74-6
• 化学式: C₂₀H₂₅F₃N₄O₆
• 分子量: 474.437
• InChiKey: FWHPUFBARDGGRL-ZCGHOXCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  137
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(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 24.0h， 以54%的产率得到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-(3,5-di-O-acetyl-2-bromo-2-deoxy-β-D-ribofuranosyl)-uracil 在 palladium diacetate 、 ammonium cerium(IV) nitrate 、 碘 、 sodium methylate 、 三乙胺 、 三苯基膦 、 锌 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 17.5h， 生成 1-(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

文献信息

• SYNTHESIS OF 5-ALKENYLATED D4T ANALOGUES VIA THE Pd-CATALYZED CROSS-COUPLING REACTION
  作者：A. Ciurea、C. Fossey、S. Benzaria、D. Gavriliu、Z. Delbederi、B. Lelong、D. Ladurée、A. M. Aubertin、A. Kirn

  DOI：10.1081/ncn-100105902

  日期：2001.9.30

  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.