1-(6-氨基-9H-嘌呤-9-基)-2-丙酮 | 105970-02-3

• 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: 1-(6-氨基-9H-嘌呤-9-基)-2-丙酮
• 英文名称: 1-(6-amino-9H-purin-9-yl)propan-2-one
• 英文别名: 1-(9-adenyl)propan-2-one；9-(2-oxopropyl)adenine；1-(6-aminopurin-9-yl)propan-2-one
• CAS: 105970-02-3
• 化学式: C₈H₉N₅O
• 分子量: 191.192
• InChiKey: QVVQIXZDNRKXPV-UHFFFAOYSA-N

物化性质

• 密度：
  1.56±0.1 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  86.7
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-(6-氨基-9H-嘌呤-9-基)-2-丙酮 在 [RuCl2(benzene)]2 、 sodium formate 、 sodium hydride 、 (R)-(+)-alpha,alpha-二苯基脯氨醇 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 60.0h， 生成 替诺福韦二乙酯
  参考文献：
  名称：

  The Synthesis of Tenofovir and Its Analogues via Asymmetric Transfer Hydrogenation

  摘要：

  A series of tenofovir analogues with potential antiviral and immunobiologically active compounds were synthesized through an asymmetric transfer hydrogenation reaction from achiral purine derivatives. Up to 97% ee and good to excellent yields were achieved under mild conditions through short reaction steps. The present report suggests an efficient process to acquire tenofovir and its analogues.

  DOI：

  10.1021/ol500583d
• 作为产物：
  描述：

  乙酰氨基嘌呤 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 1-(6-氨基-9H-嘌呤-9-基)-2-丙酮
  参考文献：
  名称：

  Antitumor agents. 86. Synthesis and cytotoxicity of .alpha.-methylene-.gamma.-lactone-bearing purines

  摘要：

  alpha-Methylene-gamma-lactones covalently linked to adenine, hypoxanthine, and guanine were synthesized by using the convenient Reformatsky-type reaction between ethyl alpha-(bromomethyl)acrylate and the proper purine ketones. In vitro cytotoxicity data demonstrated that these compounds were active against L-1210 tissue culture cells with 3 being most potent (ED50 = 0.3 microgram/mL).

  DOI：

  10.1021/jm00386a025

文献信息

• Versatile synthesis of oxime-containing acyclic nucleoside phosphonates – synthetic solutions and antiviral activity
  作者：Pavel N. Solyev、Maxim V. Jasko、Alla A. Kleymenova、Marina K. Kukhanova、Sergey N. Kochetkov

  DOI：10.1039/c5ob01571e

  日期：——

  New oxime-containing acyclic nucleoside phosphonates 9-2-[(phosphonomethyl)oximino]ethyl}adenine (1), -guanine (2) and 9-2-[(phosphonomethyl)oximino]propyl}adenine (3) with wide spectrum activity against different types of viruses were synthesized. The key intermediate, diethyl aminooxymethylphosphonate, was obtained by the Mitsunobu reaction. Modified conditions for the by-product separation (without

  新的含肟的无环核苷膦酸酯9- 2-[（膦酰基甲基）肟基]乙基}腺嘌呤（1），-鸟嘌呤（2）和9- 2-[（膦酰基甲基）肟基]丙基}腺嘌呤（3）宽合成了针对不同类型病毒的光谱活性。通过Mitsunobu反应获得关键的中间体氨基乙基氧甲基膦酸二乙酯。改进的副产物分离条件（无需色谱和蒸馏）可使我们获得85％的氨氧基中间体收率。DBU和Cs 2 CO 3对N 9 / N 7的影响研究了腺嘌呤和鸟嘌呤烷基化的产物比。发现了一种方便的氨氧基检测方法。测试了合成的膦酸酯，它们似乎显示出对不同类型病毒（HIV，细胞培养中的疱疹病毒和复制子系统中的丙型肝炎病毒）的中等活性，毒性高达1000μM。
• Enzymatic approach toward the synthesis of isotopically labeled ( R )-9-(2-hydroxypropyl)adenine
  作者：Nelo R. Rivera、Jeffrey Moore、David J. Schenk、Heather Wang、David Hesk、Ingrid Mergelsberg

  DOI：10.1016/j.tetlet.2016.01.087

  日期：2016.3

  Isotopically labeled compounds have numerous applications in drug discovery and development. (R)-9-(2-Hydroxypropyl)adenine 1 is an important intermediate in the synthesis of various acyclic nucleoside phosphonates including tenofovir. We have developed a short synthetic method to prepare deuterium and tritium labeled 1 using a ketoreductase enzyme catalyzed reduction as the key step to introduce the

  同位素标记的化合物在药物发现和开发中具有许多应用。（R）-9-（2-羟丙基）腺嘌呤1是包括替诺福韦在内的各种无环核苷膦酸酯的合成中的重要中间体。我们已经开发出一种简短的合成方法，使用酮还原酶催化的还原反应制备氘和tri标记的1，这是以高效和对映选择性方式引入标记的关键步骤。
• Regioselective N9 alkylation of purine rings assisted by β-cyclodextrin
  作者：Qian Zhang、Gang Cheng、Yong-Zhen Huang、Gui-Rong Qu、Hong-Ying Niu、Hai-Ming Guo

  DOI：10.1016/j.tet.2012.07.025

  日期：2012.9

  Under the assistance of beta-cyclodextrin, purine was effectively alkylated at N9 together with up to 99% conversion and good to excellent yield using water as the solvent. High regioselectivity-N9/N7 selectivity>99:1 was attributed to the beta-cyclodextrin cavity blocked the N7 of purines ring. (c) 2012 Elsevier Ltd. All rights reserved.
• Holy, Antonin, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 1, p. 248 - 265
  作者：Holy, Antonin

  DOI：——

  日期：——
• Rosenberg, Ivan; Holy, Antonin; Masojidkova, Milena, Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 11B, p. 2753 - 2777
  作者：Rosenberg, Ivan、Holy, Antonin、Masojidkova, Milena

  DOI：——

  日期：——