9-(2-O-acetyl-3,5-di-O-benzyl-4-C-triethylsilylethynyl-β-D-ribo-pentofuranosyl)adenine | 306305-04-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-(2-O-acetyl-3,5-di-O-benzyl-4-C-triethylsilylethynyl-β-D-ribo-pentofuranosyl)adenine
• 英文别名: 2'-O-acetyl-3',5'-di-O-benzyl-4'-C-triethylsilylethynyl adenosine；2'-O-acetyl-3',5'-di-O-benzyl-4'-C-triethylsilylethynyladenosine；[(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-4-phenylmethoxy-5-(phenylmethoxymethyl)-5-(2-triethylsilylethynyl)oxolan-3-yl] acetate
• CAS: 306305-04-4
• 化学式: C₃₄H₄₁N₅O₅Si
• 分子量: 627.816
• InChiKey: DJMRYOWZCLIQKK-GBWWDHKLSA-N

物化性质

• 沸点：
  733.6±70.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  9-(2-O-acetyl-3,5-di-O-benzyl-4-C-triethylsilylethynyl-β-D-ribo-pentofuranosyl)adenine 在 甲醇 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 26.5h， 生成 9-[(2R,4S,5R)-5-ethynyl-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-2-yl]purin-6-amine
  参考文献：
  名称：

  Syntheses of 4‘-C-Ethynyl-β-d-arabino- and 4‘-C-Ethynyl-2‘-deoxy-β-d-ribo-pentofuranosylpyrimidines and -purines and Evaluation of Their Anti-HIV Activity

  摘要：

  4'-C-Ethynyl-beta -D-arabino- and 4'-C-ethynyl-2'-deoxy-beta -D-ribo-pentofuranosylpyrine and -purine nucleosides were synthesized and evaluated for their in vitro anti-HIV activity. The key intermediate, 4-C-ethynyl- or 4-C-triethylsilylethynyl-D-ribo-pentofuranose, was prepared from D-glucose and glycosidated with various pyrimidine or purine bases. The arabino pyrimidine derivatives were prepared from the corresponding ribo derivatives via O-2,2'-anhydro nucleosides. The 2'-deoxy-ribo derivatives were synthesized by radical reduction of 2'-bromo or 2'- phenoxythiocarbonyloxy nucleosides. Among these 4'-C-ethynyl nucleosides, seven analogues proved to be potent against HIV-1 in vitro with EC50 values ranging from 0.0003 to 0.03 muM. These compounds also exerted activity against clinical and multi-dideoxy-nucleoside-resistant HIV-1 strains with comparable EC50 values. Three such 4'-C-ethynyl-2'-deoxypurine analogues including 4'-C-ethynyl-2'-deoxyadenosine and 4'-C-ethynyl-2,6-diamino-2'-deoxy-purine were less cytotoxic [selectivity indices (SIs): 975-2733] than three 4'-C-ethynyl-2-deoxycytidine analogues (SIs: 63-363). 4'-C-Ethynyl-5-fluoro-2'-deoxycytidine was least toxic (SI: >3333) and potent against all HIV strains tested.

  DOI：

  10.1021/jm000209n
• 作为产物：
  描述：

  腺嘌呤 、 (3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-2,3-diyl diacetate 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 碳酸氢钠 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 9-(2-O-acetyl-3,5-di-O-benzyl-4-C-triethylsilylethynyl-β-D-ribo-pentofuranosyl)adenine
  参考文献：
  名称：

  4′-C-ethynyl pyrimidine nucleoside compounds and pharmaceutical compositions

  摘要：

  该发明提供了由公式[I]表示的4'-C-乙炔嘧啶核苷（除了4'-C-乙炔胸腺嘧啶）：其中B代表从嘧啶及其衍生物组成的基；X代表氢原子或羟基；R代表氢原子或磷酸酯基团；以及含有任一化合物和药学上可接受的载体的药物组合物。最好，该组合物用作抗HIV药剂或治疗艾滋病的药物。

  公开号：

  US06291670B1

文献信息

• 4'-C-ethynyl pyrimidine nucleoside compounds
  申请人：——

  公开号：US20020022722A1

  公开（公告）日：2002-02-21

  The invention provides 4′-C-ethynyl pyrimidine nucleosides (other than 4′-C-ethynylthymidine) represented by formula [I]: 1 wherein B represents a base selected from the group consisting of pyrimidine and derivatives thereof; X represents a hydrogen atom or a hydroxyl group; and R represents a hydrogen atom or a phosphate residue; and a pharmaceutical composition containing any one of the compounds and a pharmaceutically acceptable carrier. Preferably, the composition is used as an anti-HIV agent or a drug for treating AIDS.

  本发明提供了4'-C-乙炔基嘧啶核苷（不包括4'-C-乙炔基胸腺嘧啶）的化合物，其化学式为[I]：其中B代表从嘧啶和其衍生物中选择的碱基；X代表氢原子或羟基；R代表氢原子或磷酸残基；以及含有上述任一化合物和药学上可接受的载体的制药组合物。优选地，该组合物用作抗HIV剂或治疗艾滋病的药物。
• 4′-C-ethynyl pyrimidine nucleosides and pharmaceutical compositions thereof
  申请人：Yamasa Corporation

  公开号：US06403568B1

  公开（公告）日：2002-06-11

  The invention provides 4′-C-ethynyl pyrimidine nucleosides (other than 4′-C-ethynylthymidine) represented by formula [I]: wherein B represents a base selected from the group consisting of pyrimidine and derivatives thereof; X represents a hydrogen atom or a hydroxyl group; and R represents a hydrogen atom or a phosphate residue; and a pharmaceutical composition containing any one of the compounds and a pharmaceutically acceptable carrier. Preferably, the composition is used as an anti-HIV agent or a drug for treating AIDS.

  本发明提供了4'-C-乙炔基嘧啶核苷（不包括4'-C-乙炔基胸腺嘧啶）的化合物，其化学式表示为[I]：其中B代表从嘧啶和其衍生物中选择的碱基；X代表氢原子或羟基；R代表氢原子或磷酸残基；以及含有任何一种化合物和药学上可接受的载体的制药组合物。优选地，该组合物用作抗HIV剂或治疗艾滋病的药物。
• 4′-C-ethynyl purine nucleoside compounds
  申请人：Yamasa Corporation

  公开号：US06333315B1

  公开（公告）日：2001-12-25

  The invention provides 4′-C-ethynyl purine nucleosides represented by formula [I]: wherein B represents a base selected from the group consisting of purine and derivatives thereof; X represents a hydrogen atom or a hydroxyl group; and R represents a hydrogen atom or a phosphate residue; and a pharmaceutical composition containing any one of the compounds and a pharmaceutically acceptable carrier. Preferably, the composition is used as an anti-HIV agent or a drug for treating AIDS.

  该发明提供了由公式[I]所表示的4'-C-乙炔基嘌呤核苷，其中B代表从嘌呤及其衍生物组成的基；X代表氢原子或羟基；R代表氢原子或磷酸残基；以及含有任何一种化合物和药学上可接受的载体的制药组合物。优选地，该组合物用作抗HIV剂或治疗艾滋病的药物。