3'-O-benzoyl-2'-deoxy-5-(8-N-trifluoroacetamido-oct-1-ynyl)-uridine | 249286-83-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3'-O-benzoyl-2'-deoxy-5-(8-N-trifluoroacetamido-oct-1-ynyl)-uridine
• 英文别名: [(2R,3S,5R)-5-[2,4-dioxo-5-[8-[(2,2,2-trifluoroacetyl)amino]oct-1-ynyl]pyrimidin-1-yl]-2-(hydroxymethyl)oxolan-3-yl] benzoate
• CAS: 249286-83-7
• 化学式: C₂₆H₂₈F₃N₃O₇
• 分子量: 551.519
• InChiKey: CSTREAQHTHNBAD-PWRODBHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3'-O-benzoyl-2'-deoxy-5-(8-N-trifluoroacetamido-oct-1-ynyl)-uridine 在 四氮唑 、 叔丁基过氧化氢 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 3'-O-benzoyl-2'-deoxy-5-(8-trifluoracetamidooct-1-ynyl)uridine 5'-(2-cyanoethoxy)-methoxycarbonylmethyl phosphate
  参考文献：
  名称：

  Syntheses of inhibitors for the enzyme thymidine 5′-diphosphate-glucose-4,6-dehydratase (EC 4.2.1.46)

  摘要：

  Inhibitors of the enzyme thymidine 5'-diphosphate-glucose-4,6-dehydratase (EC 4.2.1.46) were synthesised starting from thymidine, 2-deoxy-uridine and -cytidine. The diphosphate moieties have either been replaced by methylene diphosphonate or phosphoryl hydroxyacetic acid to yield inhibitors in a similar range to thymidine 5'-diphosphate itself. Spacers were attached to various positions, of which those at C-5 of the nucleobase were suitable analogues and showed a mixed type of inhibition characteristics, whereas attachment at other sites led to marginally active or inactive inhibitors. These investigations will prepare the ground for developing a purification procedure based on affinity chromatography. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00074-9
• 作为产物：
  描述：

  2'-脱氧-5'-O-[(叔丁基)二甲基硅烷基]-5-碘尿苷 在 吡啶 、 copper(l) iodide 、 tris(triphenylphosphine)-palladium(II) dichloride 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 三乙胺 为溶剂， 反应 10.0h， 生成 3'-O-benzoyl-2'-deoxy-5-(8-N-trifluoroacetamido-oct-1-ynyl)-uridine
  参考文献：
  名称：

  Syntheses of inhibitors for the enzyme thymidine 5′-diphosphate-glucose-4,6-dehydratase (EC 4.2.1.46)

  摘要：

  Inhibitors of the enzyme thymidine 5'-diphosphate-glucose-4,6-dehydratase (EC 4.2.1.46) were synthesised starting from thymidine, 2-deoxy-uridine and -cytidine. The diphosphate moieties have either been replaced by methylene diphosphonate or phosphoryl hydroxyacetic acid to yield inhibitors in a similar range to thymidine 5'-diphosphate itself. Spacers were attached to various positions, of which those at C-5 of the nucleobase were suitable analogues and showed a mixed type of inhibition characteristics, whereas attachment at other sites led to marginally active or inactive inhibitors. These investigations will prepare the ground for developing a purification procedure based on affinity chromatography. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00074-9

文献信息

• Syntheses of inhibitors for the enzyme thymidine 5′-diphosphate-glucose-4,6-dehydratase (EC 4.2.1.46)
  作者：Andreas Naundorf、Werner Klaffke

  DOI：10.1016/s0008-6215(99)00074-9

  日期：1999.5

  Inhibitors of the enzyme thymidine 5'-diphosphate-glucose-4,6-dehydratase (EC 4.2.1.46) were synthesised starting from thymidine, 2-deoxy-uridine and -cytidine. The diphosphate moieties have either been replaced by methylene diphosphonate or phosphoryl hydroxyacetic acid to yield inhibitors in a similar range to thymidine 5'-diphosphate itself. Spacers were attached to various positions, of which those at C-5 of the nucleobase were suitable analogues and showed a mixed type of inhibition characteristics, whereas attachment at other sites led to marginally active or inactive inhibitors. These investigations will prepare the ground for developing a purification procedure based on affinity chromatography. (C) 1999 Elsevier Science Ltd. All rights reserved.