6-chloro-9-[3-(hydroxymethyl)phenyl]purine | 469887-23-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-chloro-9-[3-(hydroxymethyl)phenyl]purine
• 英文别名: 9-[m-(hydroxymethyl)phenyl]-6-chloropurine；[3-(6-Chloropurin-9-yl)phenyl]methanol
• CAS: 469887-23-8
• 化学式: C₁₂H₉ClN₄O
• 分子量: 260.683
• InChiKey: XIWXOROFRIOOKB-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：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-chloro-9-[3-(hydroxymethyl)phenyl]purine 在 氨 作用下， 以 甲醇 为溶剂， 生成 9-[m-(hydroxymethyl)phenyl]adenine
  参考文献：
  名称：

  9-[(Hydroxymethyl)phenyl]adenines: new aryladenine substrates of adenosine deaminase

  摘要：

  New phenyl adenine compounds 5-7 were synthesized as analogues of adenosine and studied for their adenosine deaminase (ADA) substrate activity. The 9-[(o-hydroxymethyl)phenyl]methyl]adenine 5 and 9-[(m-hydroxymethyl)phenyl]adenine 7 were deaminated by ADA, and 9-[(o-hydroxyethyl)phenyl]adenine 6 was not deaminated up to 7 days. The ADA substrates 5 and 7 were deaminated quantitatively to their inosine analogues in 10 and 6 h, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00192-0
• 作为产物：
  描述：

  3-氨基苯甲醇 在 sodium thiosulfate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 6-chloro-9-[3-(hydroxymethyl)phenyl]purine
  参考文献：
  名称：

  9-[(Hydroxymethyl)phenyl]adenines: new aryladenine substrates of adenosine deaminase

  摘要：

  New phenyl adenine compounds 5-7 were synthesized as analogues of adenosine and studied for their adenosine deaminase (ADA) substrate activity. The 9-[(o-hydroxymethyl)phenyl]methyl]adenine 5 and 9-[(m-hydroxymethyl)phenyl]adenine 7 were deaminated by ADA, and 9-[(o-hydroxyethyl)phenyl]adenine 6 was not deaminated up to 7 days. The ADA substrates 5 and 7 were deaminated quantitatively to their inosine analogues in 10 and 6 h, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00192-0

文献信息

• 9-Arylpurines as a Novel Class of Enterovirus Inhibitors
  作者：Leire Aguado、Hendrik Jan Thibaut、Eva-María Priego、María-Luisa Jimeno、María-José Camarasa、Johan Neyts、María-Jesús Pérez-Pérez

  DOI：10.1021/jm901240p

  日期：2010.1.14

  Here we report on a novel class of enterovirus inhibitors that can be structurally described as 9-arylpurines. These compounds elicit activity against a variety of enteroviruses in the low μM range including Coxsackie virus A16, A21, A24, Coxsackie virus B3, and echovirus 9. Structure−activity relationship (SAR) studies indicate that a chlorine or bromine atom is required at position 6 of the purine

  在这里，我们报告了一种新型的肠道病毒抑制剂，其结构上可称为9-芳基嘌呤。这些化合物引起针对多种低μM范围内肠病毒的活性，包括柯萨奇病毒A16，A21，A24，柯萨奇病毒B3和回声病毒9。结构活性关系（SAR）研究表明，位置上需要一个氯或溴原子嘌呤环中的6个具有抗病毒活性。该系列中最具选择性的化合物以剂量依赖性方式抑制柯萨奇病毒B3复制，EC 50值约为5-8μM。在高达250μM的浓度下，未观察到对不同细胞系的毒性。此外，未检测到对TBZE-029和TTP-8307 CVB3耐药菌株的交叉耐药性。