6-Chlor-9-benzyl-7,9-dihydro-8-purinon | 21266-37-5

• 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-Chlor-9-benzyl-7,9-dihydro-8-purinon
• 英文别名: 9-benzyl-6-chloro-7H-purin-8(9H)-one；9-benzyl-6-chloro-7,9-dihydro-purin-8-one；9-benzyl-6-chloro-7H-purin-8-one
• CAS: 21266-37-5
• 化学式: C₁₂H₉ClN₄O
• 分子量: 260.683
• InChiKey: URBCXJFWJSOASL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  58.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Chlor-9-benzyl-7,9-dihydro-8-purinon 、 苯胺 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.67h， 以90%的产率得到9-benzyl-6-(phenylamino)-7H-purin-8(9H)-one
  参考文献：
  名称：

  An efficient synthesis of 6,9-disubstituted purin-8-ones via copper-catalyzed coupling/cyclization

  摘要：

  An efficient and novel synthesis of 6,9-disubstituted purin-8-ones has been developed. Starting from dichloropyrimidin-5-ylcarbamate, CuCl/amino acid catalyzed coupling/cyclization reaction with amines was achieved to afford 9-substituted 6-chloropurin-8-ones. Then a microwave-assisted amination procedure was carried out for the synthesis of 6,9-disubstituted purin-8-ones in moderate to good yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.106
• 作为产物：
  描述：

  methyl (4,6-dichloropyrimidin-5-yl) carbamate 、 苄胺 在 potassium carbonate 、 copper(l) chloride 、 L-羟基脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以81%的产率得到6-Chlor-9-benzyl-7,9-dihydro-8-purinon
  参考文献：
  名称：

  An efficient synthesis of 6,9-disubstituted purin-8-ones via copper-catalyzed coupling/cyclization

  摘要：

  An efficient and novel synthesis of 6,9-disubstituted purin-8-ones has been developed. Starting from dichloropyrimidin-5-ylcarbamate, CuCl/amino acid catalyzed coupling/cyclization reaction with amines was achieved to afford 9-substituted 6-chloropurin-8-ones. Then a microwave-assisted amination procedure was carried out for the synthesis of 6,9-disubstituted purin-8-ones in moderate to good yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.106

文献信息

• Synthesis of 6-Substituted 9-Benzyl-8-hydroxypurines with Potential Interferon-Inducing Activity
  作者：Kazunori Kazaoka、Hironao Sajiki、Kosaku Hirota

  DOI：10.1248/cpb.51.608

  日期：——

  Various 6-substituted 9-benzyl-8-hydroxypurines were synthesized in order to investigate the structure–activity relationship at the 6-position of 9-benzyl-8-hydroxyadenine (1), which is a lead compound for the screening of interferon (IFN)-inducing activity. 6-Unsubstituted, mercapto-, methylthio- and hydroxy-9-benzyl-8-hydroxypurines (2—5) were prepared from 5-amino-1-benzyl-4-cyano-2-hydroxyimidazole (9). Synthesis of a 6-methoxy analog (6) was conducted from 5-amino-4-benzylamino-6-chloropyrimidine (13). 6-Alkylamino and acylaminopurines (7 and 8) were also prepared by alkylation and acylation of 1, respectively. Since these compounds (2—8) indicated no activity, it was found that a free amino group of 1 is required for the expression of IFN-inducing activity.

  为了研究 9-苄基-8-羟基腺嘌呤（1）6-位的结构-活性关系，合成了多种 6-取代的 9-苄基-8-羟基嘌呤，而 9-苄基-8-羟基腺嘌呤是筛选干扰素（IFN）诱导活性的先导化合物。由 5-氨基-1-苄基-4-氰基-2-羟基咪唑（9）制备了 6-未取代、巯基、甲硫基和羟基-9-苄基-8-羟基嘌呤（2-5）。由 5-氨基-4-苄基氨基-6-氯嘧啶（13）合成了 6-甲氧基类似物（6）。通过 1 的烷基化和酰基化，还分别制备了 6-烷基氨基和酰基氨基嘌呤（7 和 8）。由于这些化合物（2-8）没有活性，因此发现 1 的游离氨基是表达 IFN 诱导活性的必要条件。

表征谱图