4-acetyl-1-(2-azido-2-deoxy-3,5-di-O-benzoyl-4-thio-α-D-arabino-pentofuranosyl)cytosine | 237406-90-5

• 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: 4-acetyl-1-(2-azido-2-deoxy-3,5-di-O-benzoyl-4-thio-α-D-arabino-pentofuranosyl)cytosine
• 英文别名: [(2R,3S,4S,5S)-5-(4-acetamido-2-oxopyrimidin-1-yl)-4-azido-3-benzoyloxythiolan-2-yl]methyl benzoate
• CAS: 237406-90-5
• 化学式: C₂₅H₂₂N₆O₆S
• 分子量: 534.552
• InChiKey: KBCSVRBIWMCTHX-ZDFPQIBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  154
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-acetyl-1-(2-azido-2-deoxy-3,5-di-O-benzoyl-4-thio-α-D-arabino-pentofuranosyl)cytosine 在 氨 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以93%的产率得到1-(2-azido-2-deoxy-4-thio-α-D-arabino-pentofuranosyl)cytosine
  参考文献：
  名称：

  An Alternative Synthesis of the Antineoplastic Nucleoside 4‘-ThioFAC and Its Application to the Synthesis of 4‘-ThioFAG and 4‘-Thiocytarazid

  摘要：

  Previously, we synthesized 4'-thioFAC, a novel antineoplastic cytosine nucleoside, by developing an original method. However, several problems remained. To overcome these problems, we have developed an alternative method far the synthesis of 4'-thionucleosides. In the original synthesis, carbons from C1 to C5 of D-glucose were used. The new method also starts from D-glucose but uses carbons closer to the tail (C2-C6). A dibenzoyl derivative obtained by this approach was brominated at the anomeric position to give a 1-bromide derivative. Fusion of the I-bromide and persilylated acetylcytosine, followed by deprotection, predominantly gave a beta-anomer of 4'-thioFAC. The reaction of 2,6-diaminopurine with the I-bromide in the presence of TMS triflate gave a glycosylated product in good yield. After deprotection, the resulting 1:1 anomeric mixture of free nucleosides was treated with adenosine deaminase to give a beta-anomer of 4'-thioFAG, a guanine congener of 4'-thioFAC, selectively. Using a similar approach, we synthesized 4'-thiocytarazid, which was not possible using the original method.

  DOI：

  10.1021/jo990958g
• 作为产物：
  描述：

  3-azido-3-deoxy-5,6-di-O,S-acetyl-1,2-O-isopropylidene-5-thio-α-D-gluco-pentofuranose 在 sodium periodate 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 三氟乙酸 作用下， 以 水 为溶剂， 生成 4-acetyl-1-(2-azido-2-deoxy-3,5-di-O-benzoyl-4-thio-α-D-arabino-pentofuranosyl)cytosine
  参考文献：
  名称：

  Synthetic Studies on 2′-Substituted-4′-thiocytidine Derivatives as Antineoplastic Agents

  摘要：

  As potential antineoplastic agents, we have synthesized 4'-thioFAC and 4'-thiocytarazid by developing an alternative synthetic method. 4'-ThioFAC showed potent antineoplastic activities in vivo as well as in vitro.

  DOI：

  10.1080/15257779908041569

文献信息

• Synthetic Studies on 2′-Substituted-4′-thiocytidine Derivatives as Antineoplastic Agents
  作者：Yuichi Yoshimura、Mikari Endo、Kenji Kitano、Kohei Yamada、Shinji Sakata、Shinji Miura、Haruhiko Machida

  DOI：10.1080/15257779908041569

  日期：1999.4

  As potential antineoplastic agents, we have synthesized 4'-thioFAC and 4'-thiocytarazid by developing an alternative synthetic method. 4'-ThioFAC showed potent antineoplastic activities in vivo as well as in vitro.
• An Alternative Synthesis of the Antineoplastic Nucleoside 4‘-ThioFAC and Its Application to the Synthesis of 4‘-ThioFAG and 4‘-Thiocytarazid
  作者：Yuichi Yoshimura、Mikari Endo、Shinji Miura、Shinji Sakata

  DOI：10.1021/jo990958g

  日期：1999.10.1

  Previously, we synthesized 4'-thioFAC, a novel antineoplastic cytosine nucleoside, by developing an original method. However, several problems remained. To overcome these problems, we have developed an alternative method far the synthesis of 4'-thionucleosides. In the original synthesis, carbons from C1 to C5 of D-glucose were used. The new method also starts from D-glucose but uses carbons closer to the tail (C2-C6). A dibenzoyl derivative obtained by this approach was brominated at the anomeric position to give a 1-bromide derivative. Fusion of the I-bromide and persilylated acetylcytosine, followed by deprotection, predominantly gave a beta-anomer of 4'-thioFAC. The reaction of 2,6-diaminopurine with the I-bromide in the presence of TMS triflate gave a glycosylated product in good yield. After deprotection, the resulting 1:1 anomeric mixture of free nucleosides was treated with adenosine deaminase to give a beta-anomer of 4'-thioFAG, a guanine congener of 4'-thioFAC, selectively. Using a similar approach, we synthesized 4'-thiocytarazid, which was not possible using the original method.