1-(4-C-ethynyl-2,3,5-tri-O-acetyl-β-D-arabino-pentofuranosyl)uracil | 233266-88-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-C-ethynyl-2,3,5-tri-O-acetyl-β-D-arabino-pentofuranosyl)uracil
• 英文别名: [(2R,3S,4S,5R)-3,4-diacetyloxy-5-(2,4-dioxopyrimidin-1-yl)-2-ethynyloxolan-2-yl]methyl acetate
• CAS: 233266-88-1
• 化学式: C₁₇H₁₈N₂O₉
• 分子量: 394.338
• InChiKey: YFSDHPUCOGAGRW-LJIGWXMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(4-C-ethynyl-2,3,5-tri-O-acetyl-β-D-arabino-pentofuranosyl)uracil 在 ammonium hydroxide 、 Cl₂P(O)OC₆H₄Cl 作用下， 以 1,4-二氧六环 、 吡啶 为溶剂， 生成 4'-C-ethynyl-β-D-arabino-pentofuranosyl cytosine
  参考文献：
  名称：

  Synthesis of 4′-C-Ethynyl-β-D-arabino- and 4′-C-Ethynyl-2′-deoxy-β-D-ribo- pentofuranosyl Pyrimidines, and Their Biological Evaluation

  摘要：

  4′-C-乙炔基-β-D-阿拉伯五碳呋喃糖胸腺嘧啶（14）和细胞嘧啶（16），以及4′-C-乙炔基-2′-脱氧-β-D-核糖五碳呋喃糖胸腺嘧啶（25）和细胞嘧啶（27）是通过适当保护的4′-C-羟甲基-3,5-二-O-苄基-α-D-核糖五碳呋喃糖（1）从D-葡萄糖合成的。其中，2′-脱氧衍生物25和27表现出了抗病毒活性，而胞苷衍生物16和27抑制了肿瘤细胞的生长。

  DOI：

  10.1271/bbb.63.1146
• 作为产物：
  描述：

  1-(4-C-ethynyl-2-O-acetyl-3,5-di-O-benzyl-β-D-arabino-pentofuranosyl)uracil 在 乙酸酐 、 三溴化硼 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 生成 1-(4-C-ethynyl-2,3,5-tri-O-acetyl-β-D-arabino-pentofuranosyl)uracil
  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。
• Syntheses of 4<i>‘</i><i>-</i><i>C</i>-Ethynyl-β-<scp>d</scp>-<i>arabino- </i>and 4‘-<i>C-</i>Ethynyl-2<i>‘</i>-deoxy-β-<scp>d</scp>-<i>ribo-</i>pentofuranosylpyrimidines and -purines and Evaluation of Their Anti-HIV Activity
  作者：Hiroshi Ohrui、Satoru Kohgo、Kenji Kitano、Shinji Sakata、Eiichi Kodama、Kazuhisa Yoshimura、Masao Matsuoka、Shiro Shigeta、Hiroaki Mitsuya

  DOI：10.1021/jm000209n

  日期：2000.11.1

  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.
• 4'-C-ETHYNYL PYRIMIDINE NUCLEOSIDES
  申请人：YAMASA CORPORATION

  公开号：EP1177201B1

  公开（公告）日：2003-09-24
• 4'-C-ETHYNYL PURINE NUCLEOSIDES
  申请人：YAMASA CORPORATION

  公开号：EP1177202B1

  公开（公告）日：2003-09-24
• US6291670B1
  申请人：——

  公开号：US6291670B1

  公开（公告）日：2001-09-18