6-氟嘌呤 | 1480-89-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 6-氟嘌呤
• 英文名称: 6-fluoro-9H-purine
• 英文别名: 6-fluoropurine；6-fluoro-7(9)H-purine；6-Fluoropurin；6-Fluorpurin；6-fluoro-7H-purine
• CAS: 1480-89-3
• 化学式: C₅H₃FN₄
• mdl: MFCD13189430
• 分子量: 138.104
• InChiKey: LGQVOKWMIRXXDM-UHFFFAOYSA-N

物化性质

• 沸点：
  180.1±50.0 °C(Predicted)
• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-氟嘌呤 生成 腺嘌呤
  参考文献：
  名称：

  TOMINAGA, TOSHIYOSHI;SUZUKI, KAZUTOSHI;INOUE, OSAMU;IRIE, TOSHIAKI;YAMASA+, APPL. RADIAT. AND ISOTOP., 38,(1987) N 6, 437-445

  摘要：

  DOI：
• 作为产物：
  描述：

  6-氯嘌呤 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 为溶剂， 反应 348.0h， 生成 6-氟嘌呤
  参考文献：
  名称：

  The New Convenient Synthesis of 6-Fluoropurine and Its 7-/9-Unsubstituted Analogues

  摘要：

  6-Fluoropurine and its 7-/9-unsubstituted analogues have good biological activity and serve as important pharmaceutical intermediates. This paper describes a new and convenient synthesis of 6-fluoropurine and its 7-/9-unsubstituted analogues, by first replacing the chlorine atoms with trimethylammonio groups through the reaction of 6-chloropurine and its 7-/9-unsubstituted analogues with trimethylamine, and then replacing the trimethylammonio groups with fluorine atoms using safe and cheap TBAF center dot 3H(2)O as fluorinating agent at room temperature. Compared with reported methods, the new synthesis has milder conditions, shorter reaction times, simpler post-processing and higher (or similar) yields.

  DOI：

  10.3987/com-12-12583

文献信息

• Room-Temperature Nucleophilic Aromatic Fluorination: Experimental and Theoretical Studies
  作者：Haoran Sun、Stephen G. DiMagno

  DOI：10.1002/anie.200504555

  日期：2006.4.21
• Escherichia coli mediated biosynthesis and in vitro anti-HIV activity of lipophilic 6-halo-2',3'-dideoxypurine nucleosides
  作者：Kunichika Murakami、Takuma Shirasaka、Hidetoshi Yoshioka、Eiji Kojima、Shizuko Aoki、Harry Ford、John S. Driscoll、James A. Kelley、Hiroaki Mitsuya

  DOI：10.1021/jm00109a012

  日期：1991.5

  A series of 6-substituted 2',3'-dideoxypurine ribofuranosides (ddP) was enzymatically synthesized with live E. coli in an effort to enhance the lipophilicity of this class of anti-human immunodeficiency virus (HIV) compounds and thereby facilitate drug delivery into the central nervous system. All 6-halo-substituted ddPs were substantially more lipophilic, as defined by their octanol-water partition coefficient (P), than their nonhalogenated congeners 2',3'-dideoxyinosine (ddI) or 2',3'-dideoxyguanosine (ddG). For this class of compounds, log P's ranged from +0.5 to -1.2 in the following order: 6-iodo, 2-amino-6-iodo > 6-bromo, 2-amino-6-bromo > 6-chloro, 2-amino-6-chloro > 6-fluoro, 2-amino-6-fluoro >> ddG > ddI. These compounds were evaluated in vitro for ability to suppress the infectivity, replication, and cytopathic effect of HIV. 2-Amino-6-fluoro-, 2-amino-6-chloro-, and 6-fluoro-ddP exhibited a potent activity against HIV comparable to that of ddI or ddG and completely blocked the infectivity of HIV without affecting the growth of target cells. The comparative order of in vitro anti-HIV activity was 2-amino-6-fluoro, 2-amino-6-chloro, 6-fluoro > 2-amino-6-bromo > 2-amino-6-iodo, 6-chloro > 6-bromo > 6-iodo. These compounds also exhibited potent in vitro activity against HIV-2 and 3'-azido-3'-deoxythymidine-resistant HIV-1 variants. All 2-amino-6-halo-ddPs and 6-halo-ddPs were substrates for adenosine deaminase (ADA) and were converted to ddG or ddI, respectively. In the presence of the potent ADA inhibitor 2'-deoxycoformycin, 6-halo-substituted ddPs failed to exert an in vitro antiretroviral effect. These dideoxypurine nucleoside analogues represent a new class of lipophilic prodrugs of ddG and ddI that possess the potential for more effective therapy of HIV-induced neurologic disorders.
• Mitsunobu Reactions for the Synthesis of Carbocyclic Analogues of Nucleosides: Examination of the Regioselectivity¹
  作者：Akemi Toyota、Nobuya Katagiri、Chikara Kaneko

  DOI：10.1080/00397919308011216

  日期：1993.5

  In order to provide a general synthetic method for carbocyclic nucleosides, regioselectivities in Mitsunobu reaction of purine, pyrimidin-2-one and their substituted derivatives with a variety of alcohols were examined and found to depend upon both substituents of the bases and kind of the alcohols.
• Reactivity of 6-Halopurine Analogs with Glutathione as a Radiotracer for Assessing Function of Multidrug Resistance-Associated Protein 1
  作者：Toshimitsu Okamura、Tatsuya Kikuchi、Kiyoshi Fukushi、Toshiaki Irie

  DOI：10.1021/jm901332c

  日期：2009.11.26

  6-Bromo-7-[C-11]methylpurine is reported to react with glutathione via glutathione S-transferases in the brain and to be converted into a substrate for multidrug resistance-associated protein 1 (MRP1), an efflux pump. The compound with a rapid conversion rate allows quantitative assessment of MRP1 function, but this rate is probably susceptible to interspecies differences. Hence, for application to different species, including humans, it is necessary to adjust the conversion rate by modifying the chemical structure. We therefore designed 6-Halo-9-(or 7)-[C-14]methylpurine (halogen: F, Cl, Br, or I), and evaluated them in vitro with respect to enzymatic reactivity with glutathione using brain homogenates from the mouse, rat, or monkey. There was a marked difference in reactivity between these species. Changes in the position of the methyl group and halogen on N-methyl-6-halopurine provided various compounds possessing wide-ranging reactivity with glutathione. In conclusion, the adjustment of reactivity of 6-bromo-7-[C-11]methylpurine may allow assessment of MRP1 function in the brain in various species.
• MURAKAMI, KUNICHIKA;SHIRASAKA, TAKUMA;YOSHIOKA, HIDETOSHI;KOJIMA, EIJI;AO+, J. MED. CHEM., 34,(1991) N, C. 1606-1612
  作者：MURAKAMI, KUNICHIKA、SHIRASAKA, TAKUMA、YOSHIOKA, HIDETOSHI、KOJIMA, EIJI、AO+

  DOI：——

  日期：——