1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-iodo-uracil | 386747-70-2

• 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-iodo-uracil
• 英文别名: [(2S,5R)-5-(5-iodo-2,4-dioxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methyl acetate
• CAS: 386747-70-2
• 化学式: C₁₁H₁₁IN₂O₅
• 分子量: 378.123
• InChiKey: ZJSUDTRUMDELFH-IONNQARKSA-N

物化性质

• 熔点：
  167 °C
• 密度：
  1.90±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

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-iodo-uracil 在 palladium diacetate 、 sodium methylate 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 50.0h， 生成 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-{N-[5-(methoxycarbonyl)pentyl]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：

  5'-O-acetyl-2',3'-didehydro-2',3'-dideoxyuridine 在 ammonium cerium(IV) nitrate 、 碘 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-iodo-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 fluorescent nucleoside analogs as probes for 2′-deoxyribonucleoside kinases
  作者：Yongfeng Li、Priti B. Soni、Lingfeng Liu、Xiao Zhang、Dennis C. Liotta、Stefan Lutz

  DOI：10.1016/j.bmcl.2009.12.097

  日期：2010.2

  fluorescent nucleoside analogs with modified sugar moieties (e.g., sugars other than ribose and 2′-deoxyribose). Four novel derivatives of the fluorescent thymidine analog 6-methyl-3-(β-D-2′-deoxyribofuranosyl) furano-[2,3-d]pyrimidin-2-one were synthesized via Sonogashira reaction and subsequent copper-catalyzed cycloaddition. These compounds represent promising tools for studying nucleoside metabolism

  我们正在报告具有修饰的糖部分（例如，除核糖和 2'-脱氧核糖以外的糖）的荧光核苷类似物的合成。通过 Sonogashira 反应和随后的铜催化环加成反应合成了荧光胸苷类似物 6-methyl-3-(β-D-2'-deoxyribofuranosyl) furano-[2,3 - d ]pyrimidin-2-one 的四种新型衍生物。这些化合物代表了用于研究活细胞内核苷代谢以及筛选具有新的和改进的相应核苷类似物活性的 2'-脱氧核糖核苷激酶的定向进化文库的有前途的工具。
• Synthesis of Novel C-5 Substituted d4t Analogues Bearing Linker Arms as Potential Anti-HIV Agents
  作者：D. Ladurée、C. Fossey、M. Renoud-grappin、G. Fontaine、F. Camara、D. Gavriliu、A. Ciurea、A. M. Aubertin、A. Kirn

  DOI：10.1080/15257779908041592

  日期：1999.4

  This work reports the synthesis of 2',3'-didehydro-2',3'-dideoxy-thymidine analogues bearing several kinds of amino-linker arms at the C-5 position of the pyrimidine moiety. C-5 is an attractive position since a flexible chain may permit the triphosphates to be generated. The beta-D- and beta-L-d4T analogues were synthesized following a multi-step reaction from D-ribose and D-xylose, from D- and L-arabinose (towards an oxazoline ring) or from uridine and then were reacted with alkylene diamines.