1-(2,3,5-tri-O-benzyl-4-thio-α-D-arabinofuranosyl)cytosine

• 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-(2,3,5-tri-O-benzyl-4-thio-α-D-arabinofuranosyl)cytosine
• 英文别名: 4-amino-1-[(2S,3S,4S,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)thiolan-2-yl]pyrimidin-2-one
• 化学式: C₃₀H₃₁N₃O₄S
• 分子量: 529.66
• InChiKey: DEZPSBMONSHGFT-RXIOLPMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  胞嘧啶 、 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-D-arabinofuranose 在 三甲基氯硅烷 、 六甲基二硅氮烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 1-(2,3,5-tri-O-benzyl-4-thio-α-D-arabinofuranosyl)cytosine 、 1-(2,3,5-tri-O-benzyl-4-thio-β-D-arabinofuranosyl)cytosine
  参考文献：
  名称：

  Synthesis of 4′-Thio-β-D-arabinofuranosylcytosine (4′-Thio-ara-C) and Comparison of Its Anticancer Activity with That of Ara-C

  摘要：

  4'-thio-beta-D-arabinofuranosylcytosine was synthesized by a facile route in high yields. It was evaluated for antitumor activity against a panel of human tumors, both in vitro and in vivo.

  DOI：

  10.1080/15257770008033012

文献信息

• Use of thioarabinofuranosyl compounds
  申请人：Southern Research Institute

  公开号：EP2332551A1

  公开（公告）日：2011-06-15

  Patients suffering from cancer are treated by being administered a compound represented by formula: (1), wherein each R individually is H or an aliphatic or aromatic acyl group; A is selected from the group consisting of formulae (IIa, IIb, IIc, IId), wherein X is selected from the group consisting of hydrogen, fluorine, alkoxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, amino, monoalkylamino, dialkylamino, cyano and nitro. The above compounds also inhibit DNA replication in mammalian cells.

  癌症患者可通过服用由式表示的化合物进行治疗：(1)，其中每个 R 单独为 H 或脂肪族或芳香族酰基；A 选自由式（IIa、IIb、IIc、IId）组成的组，其中 X 选自由氢、氟、烷氧基、烷基、卤代烷基、烯基、卤代烯基、炔基、氨基、单烷基氨基、二烷基氨基、氰基和硝基组成的组。上述化合物还能抑制哺乳动物细胞中 DNA 的复制。
• Synthesis of 4′-Thio-β-D-arabinofuranosylcytosine (4′-Thio-ara-C) and Comparison of Its Anticancer Activity with That of Ara-C
  作者：Kamal N. Tiwari、Anita T. Shortnacy-fowler、Loredana Cappellacci、William B. Parker、William R. Waud、John A. Montgomery、John A. Secrist

  DOI：10.1080/15257770008033012

  日期：2000.1

  4'-thio-beta-D-arabinofuranosylcytosine was synthesized by a facile route in high yields. It was evaluated for antitumor activity against a panel of human tumors, both in vitro and in vivo.