N⁴-(6-benzyloxycarbonylaminohexanoyl)-3'-O-benzoyl-2'-deoxycytidine | 249286-92-8

• 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: N⁴-(6-benzyloxycarbonylaminohexanoyl)-3'-O-benzoyl-2'-deoxycytidine
• 英文别名: [(2R,3S,5R)-2-(hydroxymethyl)-5-[2-oxo-4-[6-(phenylmethoxycarbonylamino)hexanoylamino]pyrimidin-1-yl]oxolan-3-yl] benzoate
• CAS: 249286-92-8
• 化学式: C₃₀H₃₄N₄O₈
• 分子量: 578.622
• InChiKey: LRRCRHNDAUCEPG-CLCZQPDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  156
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N⁴-(6-benzyloxycarbonylaminohexanoyl)-3'-O-benzoyl-2'-deoxycytidine 在 sodium pyrophosphate 、 N,N'-二环己基碳二亚胺 、 lithium hydroxide 、 一水合肼 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 135.0h， 以60%的产率得到(6''-benzyloxycarbonylamino-hexanoyl)-2'-deoxy-N⁴-cytidine 5'-trilithiumdiphosphate
  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 The diphosphate moieties have either been replaced by methylene diphosphonate or phosphoryl hydroxyacetic acid to yield inhibitors in a similar range to thymidine 5'-diphosphate itself.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'-脱氧胞苷盐酸盐 在 吡啶 、 咪唑 、 四丁基氟化铵 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 63.0h， 生成 N⁴-(6-benzyloxycarbonylaminohexanoyl)-3'-O-benzoyl-2'-deoxycytidine
  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 The diphosphate moieties have either been replaced by methylene diphosphonate or phosphoryl hydroxyacetic acid to yield inhibitors in a similar range to thymidine 5'-diphosphate itself.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.