3-fluoro-4-[1-(2-deoxy-β-D-ribofuranosyl)]aniline

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-fluoro-4-[1-(2-deoxy-β-D-ribofuranosyl)]aniline
• 英文别名: (2R,3S,5R)-5-(4-amino-2-fluoro-phenyl)-2-(hydroxymethyl)tetrahydrofuran-3-ol；(2R,3S,5R)-5-(4-amino-2-fluorophenyl)-2-(hydroxymethyl)oxolan-3-ol
• 化学式: C₁₁H₁₄FNO₃
• 分子量: 227.235
• InChiKey: SPHVDJFKAKVINO-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  75.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-deoxy-D-ribose 在 咪唑 、 三苯胂 、 四丁基氟化铵 、 溴 、 palladium diacetate 、 三乙酰氧基硼氢化钠 、 二异丁基氢化铝 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 170.0h， 生成 3-fluoro-4-[1-(2-deoxy-β-D-ribofuranosyl)]aniline
  参考文献：
  名称：

  Syntheses of 4-[1-(2-deo×y-β-<FONT SIZE=-1>D</FONT>-ribofuranosyl)]-derivatives of 2-substituted-5-fluoroaniline: "cytosine replacement" analogs of deo×ycytidine for evaluation as anticancer and antihuman immunodeficiency virus (anti-HIV) agents

  摘要：

  A group of 4-[1-(2-deoxy-beta-D-ribofuranosyl)]-derivatives of 5-fluoroaniline possessing a variety of aryl C-2 substituents (6a R = H, 6b R = F, 6c R = Me) were synthesized. Accordingly, a Heck-type coupling reaction of the 4-iodoaniline derivatives (13a-c) with the bis(tert-butyldimethylsilyl)glycal (11) in the presence of Pd(OAc)(2) and Ph3As, followed by removal of the tert-butyldimethylsilyl protection groups using n-Bu4N+F-, yielded the corresponding 4-(beta-D-glycero-pentofuran-3-ulos-1-yl)aniline derivatives (14a-c) having a C-3 C=O in the sugar ring. Reduction of the C-3 C=O compounds (14a-c) using NaB(OAc)(3)H afforded the target 4-[1-(2-deoxy-beta-D-ribofuranosyl)]-derivatives of the respective 2-substituted-5-fluoroaniline (6a-c). The deoxycytidine mimic, 3-fluoro-4-[1-(2-deoxy-beta-D-ribofuranosyl)]aniline (6a), in which the cytosine ring of deoxycytidine is replaced by a 4-(3-fluoroaniline) ring system, was inactive as an anticancer agent against a variety of tumor cell lines, and as an antihuman immunodeficiency virus (HIV-1, HIV-2) agent. The failure of this unnatural deoxycytidine mimic (6a) to exhibit anticancer-antiviral activity may be due to its inability to undergo phosphorylation by host cell- and virus-induced kinases.

  DOI：

  10.1139/cjc-78-8-1081

文献信息

• Syntheses of 4-[1-(2-deo×y-β-&lt;FONT SIZE=-1&gt;D&lt;/FONT&gt;-ribofuranosyl)]-derivatives of 2-substituted-5-fluoroaniline: "cytosine replacement" analogs of deo×ycytidine for evaluation as anticancer and antihuman immunodeficiency virus (anti-HIV) agents
  作者：Zhi-Xian Wang、Leonard I. Wiebe、Erik De Clercq、Jan Balzarini、Edward E. Knaus

  DOI：10.1139/cjc-78-8-1081

  日期：——

  A group of 4-[1-(2-deoxy-beta-D-ribofuranosyl)]-derivatives of 5-fluoroaniline possessing a variety of aryl C-2 substituents (6a R = H, 6b R = F, 6c R = Me) were synthesized. Accordingly, a Heck-type coupling reaction of the 4-iodoaniline derivatives (13a-c) with the bis(tert-butyldimethylsilyl)glycal (11) in the presence of Pd(OAc)(2) and Ph3As, followed by removal of the tert-butyldimethylsilyl protection groups using n-Bu4N+F-, yielded the corresponding 4-(beta-D-glycero-pentofuran-3-ulos-1-yl)aniline derivatives (14a-c) having a C-3 C=O in the sugar ring. Reduction of the C-3 C=O compounds (14a-c) using NaB(OAc)(3)H afforded the target 4-[1-(2-deoxy-beta-D-ribofuranosyl)]-derivatives of the respective 2-substituted-5-fluoroaniline (6a-c). The deoxycytidine mimic, 3-fluoro-4-[1-(2-deoxy-beta-D-ribofuranosyl)]aniline (6a), in which the cytosine ring of deoxycytidine is replaced by a 4-(3-fluoroaniline) ring system, was inactive as an anticancer agent against a variety of tumor cell lines, and as an antihuman immunodeficiency virus (HIV-1, HIV-2) agent. The failure of this unnatural deoxycytidine mimic (6a) to exhibit anticancer-antiviral activity may be due to its inability to undergo phosphorylation by host cell- and virus-induced kinases.