Benzoic acid (2S,5R)-5-{4-[N'-(2-hydroxy-benzoyl)-hydrazino]-2-oxo-2H-pyrimidin-1-yl}-tetrahydro-furan-2-ylmethyl ester | 379262-08-5

• 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: Benzoic acid (2S,5R)-5-{4-[N'-(2-hydroxy-benzoyl)-hydrazino]-2-oxo-2H-pyrimidin-1-yl}-tetrahydro-furan-2-ylmethyl ester
• CAS: 379262-08-5
• 化学式: C₂₃H₂₂N₄O₆
• 分子量: 450.451
• InChiKey: CZMVOHDJIFQDIV-OXJNMPFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  131.78
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2S,5R)-5-{4-[N'-(2-hydroxy-benzoyl)-hydrazino]-2-oxo-2H-pyrimidin-1-yl}-tetrahydro-furan-2-ylmethyl ester 在 氨 作用下， 以 甲醇 为溶剂， 以72%的产率得到2-hydroxy-N'-[1-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2-oxo-pyrimidin-4-yl]benzohydrazide
  参考文献：
  名称：

  SYNTHESIS AND ANTIVIRAL EVALUATION OF C-4-HYDRAZIDE DERIVATIVES OF 2′,3′-DIDEOXYCYTIDINE

  摘要：

  Syntheses of three hitherto unknown derivatives of 2',3'-dideoxycytidine, namely C-4-(salicylic hydrazide)-ddC, C-4-(N-butyloxycarbonyl-isoleucine hydrazide)-ddC and its N-unprotected chlorhydrate salt have been carried out. These compounds do not induce inhibition of HIV-1 replication in cell culture experiments. Nevertheless, the modifications on the base moiety increased in all cases the lipophilicity of the parent molecule with an acceptable water solubility compared to ddC.

  DOI：

  10.1081/ncn-100002484
• 作为产物：
  描述：

  1-(5-O-benzoyl-2,3-dideoxy-β-D-glycero-pentofuranosyl)uracil 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 Benzoic acid (2S,5R)-5-{4-[N'-(2-hydroxy-benzoyl)-hydrazino]-2-oxo-2H-pyrimidin-1-yl}-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  SYNTHESIS AND ANTIVIRAL EVALUATION OF C-4-HYDRAZIDE DERIVATIVES OF 2′,3′-DIDEOXYCYTIDINE

  摘要：

  Syntheses of three hitherto unknown derivatives of 2',3'-dideoxycytidine, namely C-4-(salicylic hydrazide)-ddC, C-4-(N-butyloxycarbonyl-isoleucine hydrazide)-ddC and its N-unprotected chlorhydrate salt have been carried out. These compounds do not induce inhibition of HIV-1 replication in cell culture experiments. Nevertheless, the modifications on the base moiety increased in all cases the lipophilicity of the parent molecule with an acceptable water solubility compared to ddC.

  DOI：

  10.1081/ncn-100002484