2-氨基-6-((4-氯苯基)硫烷基)嘌呤 | 158665-15-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 2-氨基-6-((4-氯苯基)硫烷基)嘌呤
• 英文名称: 2-amino-6-[(4-chlorophenyl)sulfanyl]purine
• 英文别名: 2-amino-6-(4chlorophenylthio)-9H-purine；2-amino-6-<(4-chlorophenyl)sulfanyl>purine；6-(4-chlorophenylthio)-9H-purin-2-amine；2-amino-6-[(4-chlorophenyl)thio]purine；2-Amino-6-(4-chlorophenylthio)purine；6-(4-chlorophenyl)sulfanyl-7H-purin-2-amine
• CAS: 158665-15-7
• 化学式: C₁₁H₈ClN₅S
• 分子量: 277.737
• InChiKey: MHTZJBADMFHCCW-UHFFFAOYSA-N

物化性质

• 沸点：
  432.0±55.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氨基-6-((4-氯苯基)硫烷基)嘌呤 在 吡啶 、 sodium tetrahydroborate 、 镍 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 二乙二醇二甲醚 、 水 、 二甲基亚砜 为溶剂， 反应 37.5h， 生成 泛昔洛韦
  参考文献：
  名称：

  Convenient syntheses of 9-[4-hydroxy-3-(hydroxymethyl)butyl]guanine (penciclovir) and 9-[4-acetoxy-3-(acetoxymethyl)butyl]-2-amino-9H-purine (famciclovir)

  摘要：

  Guanine 11 was converted, in a one pot reaction, into 2-amino-6-[(4-chlorophenyl)sulfanyl]purine 9a in 88% isolated yield. 4-Acetoxy-3-(acetoxymethyl)butanol 23 was prepared from 2-chloroethanol in five steps and in 46% overall yield. The mesylate ester of compound 23 reacted with 9a in the presence of potassium carbonate with a high degree of regioselectivity (89%) to give the N-9 alkylated product 26 which was isolated in 80% yield. Acidic hydrolysis of the latter compound 26 gave penciclovir 4 in virtually quantitative yield. Penciclovir 4 and famciclovir 5 were prepared from 2-amino-6-[(4-chlorophenyl)sulfanyl]puri 9a in four and five steps, respectively, by procedures involving initial alkylation with 1,2-dibromoethane. The overall yields obtained were 65 and ca. 60%, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00169-6
• 作为产物：
  描述：

  2',3',5'-三乙酰鸟苷 在 三氟化硼乙醚 、 四乙基氯化铵 、 N,N-二甲基苯胺 、 三乙胺 、 三氯氧磷 、 苯酚 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.17h， 生成 2-氨基-6-((4-氯苯基)硫烷基)嘌呤
  参考文献：
  名称：

  鸟苷转化为阿昔洛韦及其6-脱氧衍生物

  摘要：

  2-氨基-6-（4-氯苯硫基）-（2,3,5-三-O-乙酰基-β-D-呋喃呋喃糖基）嘌呤11，可以通过允许相应的6-氯化合物10容易地制备在室温下与4-氯（硫酚）和三乙胺在甲醇溶液中反应，与三氟化硼二乙醚在沸腾的二氯甲烷溶液中反应，得到2-氨基-6-（4-氯苯基-硫代）-9 H-嘌呤12。高分离产率。9 - [（2-乙酰氧基乙氧基）甲基] -2-氨基-6-（4-氯苯硫基）-9 ħ嘌呤13，从后者苷元制备12以良好的收率，通过四个步骤转化成阿昔洛韦1然后分两步合成6-脱氧阿昔洛韦2。

  DOI：

  10.1016/s0040-4020(01)85386-2

文献信息

• Pd/PTABS: Low-Temperature Thioetherification of Chloro(hetero)arenes
  作者：Siva Sankar Murthy Bandaru、Shatrughn Bhilare、Jesvita Cardozo、Nicolas Chrysochos、Carola Schulzke、Yogesh S. Sanghvi、Krishna Chaitanya Gunturu、Anant R. Kapdi

  DOI：10.1021/acs.joc.9b00840

  日期：2019.7.19

  Heteroarenes of commercial relevance such as purines and pyrimidines were also found to be useful substrates for the reported transformation. The commercial drug Imuran (azathioprine) was synthesized as an example, and its preparation could be optimized. DFT studies were performed to understand the electronic effects of the tested ligands on the catalytic reaction.

  杂芳基氯化物的硫醚化是必不可少的合成方法，可用于获得生物活性药物和农药。由于它们的（实际或潜在的）工业重要性，出于经济和生态方面的原因，需要开发一种有效的低温协议来获取这些化合物。因此，开发了一种仅在50°C下使用Pd / PTABS系统的高效催化方案。高效率地进行了氯杂芳烃与各种反应性较低的芳基硫醇和烷基硫醇之间的偶联。还发现具有商业意义的杂芳烃，例如嘌呤和嘧啶，是报道的转化的有用底物。以合成的商品药物Imuran（硫唑嘌呤）为例，可以优化其制备方法。
• Synthesis and antiviral evaluation of novel open-chain analogues of neplanocin A
  作者：Joon Hee Hong、So-Young Kim、Chang-Hyun Oh、Kyung Ho Yoo、Jung-Hyuck Cho

  DOI：10.1080/15257770500544578

  日期：2006.4.1

  Novel acyclic nucleoside analogues were designed and synthesized as open-chain analogues of neplanocin A. The coupling of the allylic bromide with purine bases using cesium carbonate afforded a series of novel acyclic nucleosides. The synthesized compounds Ia – II were evaluated for their antiviral activity against various viruses such as HIV, HSV-1, HSV-2, and ECMV.

  新的无环核苷类似物被设计和合成为 neplanocin A 的开链类似物。烯丙基溴与嘌呤碱使用碳酸铯的偶联提供了一系列新的无环核苷。评估了合成的化合物 Ia-II 对各种病毒（如 HIV、HSV-1、HSV-2 和 ECMV）的抗病毒活性。
• AN IMPROVED PROCESS FOR THE PREPARATION OF PURINES
  申请人：Joshi Anna Ramesh

  公开号：US20050215787A1

  公开（公告）日：2005-09-29

  The present invention relates to a process for the preparation of Purines. More particularly it relates to the preparation of Purines of formula (1) wherein X is hydrogen, thioaryl; R 1 and R 2 are hydrogen or acetyl.

  本发明涉及一种制备嘌呤的方法。更具体地，它涉及制备公式（1）中的嘌呤，其中X是氢、硫芳基；R1和R2是氢或乙酰基。
• Production of nucleoside analogues
  申请人：Reese, Colin

  公开号：EP0664294A1

  公开（公告）日：1995-07-26

  A process for the preparation of a purine derivative corresponding to the following general formula: characterised in that it comprises: protecting the hydroxyl groups of the sugar moiety of a starting material corresponding to the following general formula: activating the 6-position of the purine ring; introducing the substituent B at this position; and removing the sugar moiety; wherein    A represents NH₂ or H;    B represents a substituent which has the effect of favouring subsequent substitution at the 9-position of the purine ring and which will withstand removal of the sugar moiety, but which may later be removed or converted; and    Z represents: is disclosed. The present purine derivatives obtainable by the above process may be used in a disclosed process for the preparation of a nucleoside analogue characterised in that it comprises; introducing a side chain at the 9-position of the purine derivative; and removing or converting the substituent B at the 6-position of the purine derivative.

  一种制备通式如下的嘌呤衍生物的工艺： 其特征在于，该工艺包括： 保护与下式通式相对应的起始原料中糖分子的羟基： 活化嘌呤环的 6 位；在该位上引入取代基 B； 去除糖基； 其中 A 代表 NH₂ 或 H； B 代表一种取代基，其作用是有利于随后在嘌呤环的 9 位进行取代，并能承受糖基的移除，但随后可能被移除或转化； 以及 Z 代表 已公开。 通过上述工艺获得的本嘌呤衍生物可用于已公开的制备核苷类似物的工艺中，其特征在于该工艺包括：在嘌呤衍生物的 9 位上引入侧链；以及去除或转化嘌呤衍生物 6 位上的取代基 B。
• Convenient syntheses of 9-[4-hydroxy-3-(hydroxymethyl)butyl]guanine (penciclovir) and 9-[4-acetoxy-3-(acetoxymethyl)butyl]-2-amino-9H-purine (famciclovir)
  作者：Briony Brand、Colin B Reese、Quanlai Song、Cristina Visintin

  DOI：10.1016/s0040-4020(99)00169-6

  日期：1999.4

  Guanine 11 was converted, in a one pot reaction, into 2-amino-6-[(4-chlorophenyl)sulfanyl]purine 9a in 88% isolated yield. 4-Acetoxy-3-(acetoxymethyl)butanol 23 was prepared from 2-chloroethanol in five steps and in 46% overall yield. The mesylate ester of compound 23 reacted with 9a in the presence of potassium carbonate with a high degree of regioselectivity (89%) to give the N-9 alkylated product 26 which was isolated in 80% yield. Acidic hydrolysis of the latter compound 26 gave penciclovir 4 in virtually quantitative yield. Penciclovir 4 and famciclovir 5 were prepared from 2-amino-6-[(4-chlorophenyl)sulfanyl]puri 9a in four and five steps, respectively, by procedures involving initial alkylation with 1,2-dibromoethane. The overall yields obtained were 65 and ca. 60%, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.