6-(2-furyl)-9-(4-methoxyphenylmethyl)-2-nitro-9H-purine | 917480-02-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 6-(2-furyl)-9-(4-methoxyphenylmethyl)-2-nitro-9H-purine
• 英文别名: 6-(2-Furyl)-9-[(4-methoxyphenyl)methyl]-2-nitro-purine；6-(furan-2-yl)-9-[(4-methoxyphenyl)methyl]-2-nitropurine
• CAS: 917480-02-5
• 化学式: C₁₇H₁₃N₅O₄
• 分子量: 351.321
• InChiKey: UXADUMZAUQBNTP-UHFFFAOYSA-N

物化性质

• 熔点：
  182-183 °C
• 沸点：
  650.2±65.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-(2-furyl)-9-(4-methoxyphenylmethyl)-2-nitro-9H-purine 在 四丁基氢氧化铵 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 48.02h， 以68%的产率得到6-(2-Furyl)-9-[(4-methoxyphenyl)methyl]purin-2-ol
  参考文献：
  名称：

  Purine compounds

  摘要：

  这项发明提供了一种抗分枝杆菌的6-芳基-9-(m-或p-取代苄基)嘌呤和嘌呤类似化合物。

  公开号：

  US20070203159A1
• 作为产物：
  描述：

  6-chloro-9-(4-methoxybenzyl)-9H-purine 在 bis-triphenylphosphine-palladium(II) chloride 四丁基硝酸铵 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 6-(2-furyl)-9-(4-methoxyphenylmethyl)-2-nitro-9H-purine
  参考文献：
  名称：

  A Novel Method for the Introduction of Fluorine into the Purine 2-Position: Synthesis of 2-Fluoroadenosine and a Formal Synthesis of the Antileukemic Drug Fludarabine

  摘要：

  文中描述并应用了一种新颖的方法，将氟引入嘌呤的2位，用于合成一种具有潜在抗分枝杆菌活性的化合物。此外，首次通过以过苯甲酰化的2-硝基腺苷为关键中间体，从腺苷合成了2-氟腺苷。该方法采用温和的反应条件，所需合成步骤较少。这种新颖的氟腺苷合成可视为抗白血病药物氟达拉滨磷酸盐的形式合成。

  DOI：

  10.1055/s-2006-942544

文献信息

• Purine compounds
  申请人：Gundersen Lise-Lotte

  公开号：US20070203159A1

  公开（公告）日：2007-08-30

  The invention provides an antimycobacterial 6-aryl-9-(m- or p-substituted-benzyl) purine and purine analog compounds.

  这项发明提供了一种抗分枝杆菌的6-芳基-9-(m-或p-取代苄基)嘌呤和嘌呤类似化合物。
• Synthesis and biological evaluation of pyrimidine analogs of antimycobacterial purines
  作者：Matthew L. Read、Morten Brændvang、Pedro O. Miranda、Lise-Lotte Gundersen

  DOI：10.1016/j.bmc.2010.04.035

  日期：2010.6.1

  Pyrimidine analogs of antimycobacterial 6-aryl-9-benzylpurines have been synthesized and screened for antibacterial activity against Mycobacterium tuberculosis H(37)Rv in vitro. Several active compounds were identified and the best results were observed for 5-formamidopyrimidines. These compounds generally displayed IC(90) values <= 1 mu g/mL, and they exhibited low toxicity towards mammalian cells. Imidazolylpyrimidines, which may be regarded as fleximer analogs of the parent purines, were also synthesized and one of them was found to be quite a potent inhibitor of M. tuberculosis (IC(90) 14 mu g/mL). (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and antimycobacterial activity of 5-formylaminopyrimidines; analogs of antibacterial purines
  作者：Morten Brændvang、Colin Charnock、Lise-Lotte Gundersen

  DOI：10.1016/j.bmcl.2009.04.082

  日期：2009.6

  Pyrimidine analogs of antimycobacterial purines have been synthesized and their biological activities evaluated. Several 5-formamidopyrimidines exhibited profound activity against Mycobacterium tuberculosis in vitro (IC90 <= 1.5 mu g/mL), and they were essentially inactive against other bacteria. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis, biological activity, and SAR of antimycobacterial 2- and 8-substituted 6-(2-furyl)-9-(p-methoxybenzyl)purines
  作者：Morten Brændvang、Lise-Lotte Gundersen

  DOI：10.1016/j.bmc.2007.07.034

  日期：2007.11

  A Number of 6-(2-furyl)-9-(p-methoxybenzyl)purines carrying a variety of substituents in the 2- or 8-position have been synthesized and their ability to inhibit growth of mycobacterium tuberculosis in vitro has been determined. It is demonstrated that sterical hindrance in the purine 8-position reduces activity and that C-8 should be unsubstituted. In the purine 2-position small, hydrophobic substituents are beneficial. The electronic properties of the 2-substituents appear to have only a minor influence on bioactivity. The compounds studied exhibit low toxicity toward mammalian cells (VERO cells) and are essentially inactive toward Staphylococcus aureus and Escherichia coli. The most active and selective antimycobacterial in the series detected to date is the novel 2-methyl-6-furyl-9-(p-methoxybenzyl)purine with MIC = 0.20 ug/mL- against M. tuberculosis and IC50 against VERO cells >62.5 mu g/ mL. Also the novel 2-fluoro analog and the previously known 2-chloro compound, both with MIC = 0.39 mu g/mL, are highly interestinq drug candidates. (C) 2007 Elsevier Ltd. All rights reserved.
• A Novel Method for the Introduction of Fluorine into the Purine 2-Position: Synthesis of 2-Fluoroadenosine and a Formal Synthesis of the Antileukemic Drug Fludarabine
  作者：Lise-Lotte Gundersen、Morten Brændvang

  DOI：10.1055/s-2006-942544

  日期：——

  A novel method for the introduction of fluorine in the purine 2-position is described and employed in the synthesis of a potential antimycobacterial compound. Also 2-fluoroadenosine has been synthesized for the first time from adenosine with perbenzo­ylated 2-nitroadenosine as a key intermediate. Mild reaction conditions are employed and few synthetic steps are required. The novel synthesis of fluoroadenosine can be regarded as a formal synthesis of the antileukemic drug fludarabine phosphate.

  文中描述并应用了一种新颖的方法，将氟引入嘌呤的2位，用于合成一种具有潜在抗分枝杆菌活性的化合物。此外，首次通过以过苯甲酰化的2-硝基腺苷为关键中间体，从腺苷合成了2-氟腺苷。该方法采用温和的反应条件，所需合成步骤较少。这种新颖的氟腺苷合成可视为抗白血病药物氟达拉滨磷酸盐的形式合成。