5-((E)-2-Chloro-vinyl)-2,4-bis-trimethylsilanyloxy-pyrimidine | 87782-42-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-((E)-2-Chloro-vinyl)-2,4-bis-trimethylsilanyloxy-pyrimidine
• 英文别名: [5-[(E)-2-chloroethenyl]-2-trimethylsilyloxypyrimidin-4-yl]oxy-trimethylsilane
• CAS: 87782-42-1
• 化学式: C₁₂H₂₁ClN₂O₂Si₂
• 分子量: 316.935
• InChiKey: IQLRLOPMWVVVBB-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.24
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-((E)-2-Chloro-vinyl)-2,4-bis-trimethylsilanyloxy-pyrimidine 在 三氟甲磺酸三甲基硅酯 、 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (E)-5-(2-chlorovinyl)-1-(4-thio-α-D-arabinofuranosyl)uracil
  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：

  六甲基二硅氮烷 、 5-(2-chloro-vinyl)-1H-pyrimidine-2,4-dione 在 硫酸氢铵 作用下， 生成 5-((E)-2-Chloro-vinyl)-2,4-bis-trimethylsilanyloxy-pyrimidine
  参考文献：
  名称：

  核苷。129.抗病毒核苷的合成：5-烯基-1-（2-脱氧-2-氟-β-D-阿拉伯呋喃糖基）尿嘧啶。

  摘要：

  合成了在C-5处含有乙烯基（4a），2-卤代戊基（4b-d）或乙基取代基的1-（2-脱氧-2-氟-β-D-阿拉伯呋喃糖基）尿嘧啶。发现这些核苷对HSV-1的活性比2'-氟-5-碘-ara-C（FIAC）的对数活性低，但与FIAC相比，它们对正常人淋巴细胞的细胞毒性小得多。核苷4a和4e对HSV-1（分别为ED50 = 0.16和0.24 microM）和HSV-2（ED50 = 0.69和0.65 microM）表现出良好的活性，几乎没有细胞毒性（ID50大于100 microM）。

  DOI：

  10.1021/jm00367a020

文献信息

• Nucleosides. 129. Synthesis of antiviral nucleosides: 5-alkenyl-1-(2-deoxy-2-fluoro-.beta.-D-arabinofuranosyl)uracils
  作者：Kyoichi A. Watanabe、Tsann Long Su、Uri Reichman、Nancy Greenberg、Carlos Lopez、Jack J. Fox

  DOI：10.1021/jm00367a020

  日期：1984.1

  Synthesis of 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)uracils containing a vinyl (4a), 2-halovinyl (4b-d), or ethyl substituent at C-5 was achieved. These nucleosides were found to be about a log order less active than 2'-fluoro-5-iodo-ara-C (FIAC) against HSV-1, but they are much less cytotoxic against normal human lymphocytes than FIAC. Nucleosides 4a and 4e showed good activity against HSV-1

  合成了在C-5处含有乙烯基（4a），2-卤代戊基（4b-d）或乙基取代基的1-（2-脱氧-2-氟-β-D-阿拉伯呋喃糖基）尿嘧啶。发现这些核苷对HSV-1的活性比2'-氟-5-碘-ara-C（FIAC）的对数活性低，但与FIAC相比，它们对正常人淋巴细胞的细胞毒性小得多。核苷4a和4e对HSV-1（分别为ED50 = 0.16和0.24 microM）和HSV-2（ED50 = 0.69和0.65 microM）表现出良好的活性，几乎没有细胞毒性（ID50大于100 microM）。
• 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).