7-[(3S,4S,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)thiolan-2-yl]purin-6-amine | 191794-52-2

• 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: 7-[(3S,4S,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)thiolan-2-yl]purin-6-amine
• CAS: 191794-52-2
• 化学式: C₃₁H₃₁N₅O₃S
• 分子量: 553.685
• InChiKey: IVMNQZQSGDARRF-MEXHRCSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  7-[(3S,4S,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)thiolan-2-yl]purin-6-amine 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3S,4S,5R)-2-(6-aminopurin-7-yl)-5-(hydroxymethyl)thiolane-3,4-diol 、 (2S,3S,4S,5R)-2-(6-aminopurin-7-yl)-5-(hydroxymethyl)thiolane-3,4-diol
  参考文献：
  名称：

  A Facile, Alternative Synthesis of 4‘-Thioarabinonucleosides and Their Biological Activities

  摘要：

  4'-Thioarabinonucleosides, which are potential antiviral agents, were synthesized from D-glucose. 1,4-Anhydro-4-thioarabitol (8), which can be derived from diacetone glucose in nine steps, was subjected to Pummerer rearrangement after protection of the hydroxyl groups to give 1-O-acetyl-4-thioarabinose (II), which was condensed with nucleobases to give 4'-thioarabinonucleosides. The 5-substituted-4'-thioaraU (6a-e) derivatives showed anti-HSV-1 activity (ED50 = 0.43-3.50 mu g/mL). 4'-ThioaraG (6h) and 2,6-diaminopurine 4'-thioarabinonucleoside (4'-thioaraDAP, 6g) showed antiviral activity against several herpes viruses and were particularly potent against human cytomegalovirus (0.010 and 0.022 mu g/mL, respectively).

  DOI：

  10.1021/jm9701536
• 作为产物：
  描述：

  3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose 在 ammonium sulfate 、 三氟甲磺酸三甲基硅酯 、 sodium hydride 、 间氯过氧苯甲酸 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 7-[(3S,4S,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)thiolan-2-yl]purin-6-amine
  参考文献：
  名称：

  A Facile, Alternative Synthesis of 4‘-Thioarabinonucleosides and Their Biological Activities

  摘要：

  4'-Thioarabinonucleosides, which are potential antiviral agents, were synthesized from D-glucose. 1,4-Anhydro-4-thioarabitol (8), which can be derived from diacetone glucose in nine steps, was subjected to Pummerer rearrangement after protection of the hydroxyl groups to give 1-O-acetyl-4-thioarabinose (II), which was condensed with nucleobases to give 4'-thioarabinonucleosides. The 5-substituted-4'-thioaraU (6a-e) derivatives showed anti-HSV-1 activity (ED50 = 0.43-3.50 mu g/mL). 4'-ThioaraG (6h) and 2,6-diaminopurine 4'-thioarabinonucleoside (4'-thioaraDAP, 6g) showed antiviral activity against several herpes viruses and were particularly potent against human cytomegalovirus (0.010 and 0.022 mu g/mL, respectively).

  DOI：

  10.1021/jm9701536

文献信息

• A Facile, Alternative Synthesis of 4‘-Thioarabinonucleosides and Their Biological Activities
  作者：Yuichi Yoshimura、Mikari Watanabe、Hiroshi Satoh、Noriyuki Ashida、Katsushi Ijichi、Shinji Sakata、Haruhiko Machida、Akira Matsuda

  DOI：10.1021/jm9701536

  日期：1997.7.1

  4'-Thioarabinonucleosides, which are potential antiviral agents, were synthesized from D-glucose. 1,4-Anhydro-4-thioarabitol (8), which can be derived from diacetone glucose in nine steps, was subjected to Pummerer rearrangement after protection of the hydroxyl groups to give 1-O-acetyl-4-thioarabinose (II), which was condensed with nucleobases to give 4'-thioarabinonucleosides. The 5-substituted-4'-thioaraU (6a-e) derivatives showed anti-HSV-1 activity (ED50 = 0.43-3.50 mu g/mL). 4'-ThioaraG (6h) and 2,6-diaminopurine 4'-thioarabinonucleoside (4'-thioaraDAP, 6g) showed antiviral activity against several herpes viruses and were particularly potent against human cytomegalovirus (0.010 and 0.022 mu g/mL, respectively).