[(2R,3S,4S,5R)-3,4-diacetyloxy-2-ethynyl-5-[2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]oxolan-2-yl]methyl acetate | 233266-92-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4S,5R)-3,4-diacetyloxy-2-ethynyl-5-[2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]oxolan-2-yl]methyl acetate
• CAS: 233266-92-7
• 化学式: C₁₉H₁₉N₅O₈
• 分子量: 445.389
• InChiKey: UIIPQHPSLQOOLO-IMBTUZDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R)-3,4-diacetyloxy-2-ethynyl-5-[2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]oxolan-2-yl]methyl acetate 在 ammonium hydroxide 作用下， 以 1,4-二氧六环 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-(2-O-acetyl-3,5-di-O-benzyl-4-C-ethynyl-β-D-ribo-pentofuranosyl)uracil 在 sodium hydroxide 、 Cl₂P(O)OC₆H₄Cl 、 三溴化硼 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 [(2R,3S,4S,5R)-3,4-diacetyloxy-2-ethynyl-5-[2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]oxolan-2-yl]methyl acetate
  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

文献信息

• Synthesis of 4′-<i>C</i>-Ethynyl-β-<scp>D</scp>-<i>arabino</i>- and 4′-<i>C</i>-Ethynyl-2′-deoxy-β-<scp>D</scp>-<i>ribo</i>- pentofuranosyl Pyrimidines, and Their Biological Evaluation
  作者：Satoru KOHGO、Hiroko HORIE、Hiroshi OHRUI

  DOI：10.1271/bbb.63.1146

  日期：1999.1

  4′-C-Ethynyl-β-D-arabino-pentofuranosyl thymine (14) and cytosine (16), and 4′-C-ethynyl-2′-deoxy-β-D-ribo-pentofuranosyl thymine (25) and cytosine (27) were synthesized by properly protected 4′-C-hydroxy-methyl-3,5-di-O-benzyl-α-D-ribo-pentofuranose (1) from D-glucose. Among them, 2′-deoxy derivatives 25 and 27 exhibited antiviral activity, while cytidine derivatives 16 and 27 inhibited the growth of neoplastic cells.

  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。
• 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.