2-amino-6-(2-furyl)-9-(4-methoxyphenylmethyl)-9H-purine | 442685-21-4

• 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: 2-amino-6-(2-furyl)-9-(4-methoxyphenylmethyl)-9H-purine
• 英文别名: 6-(2-Furyl)-9-[(4-methoxyphenyl)methyl]purin-2-amine；6-(furan-2-yl)-9-[(4-methoxyphenyl)methyl]purin-2-amine
• CAS: 442685-21-4
• 化学式: C₁₇H₁₅N₅O₂
• 分子量: 321.338
• InChiKey: LCUMBBXSKKIJQK-UHFFFAOYSA-N

物化性质

• 熔点：
  235-237 °C (decomp)
• 沸点：
  619.2±65.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 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：
  92
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-6-(2-furyl)-9-(4-methoxyphenylmethyl)-9H-purine 在 二碘甲烷 、 亚硝酸异戊酯 作用下， 反应 1.25h， 以40%的产率得到6-(2-furyl)-2-iodo-9-(4-methoxyphenylmethyl)-9H-purine
  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：

  2-氨基-6-溴嘌呤 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-amino-6-(2-furyl)-9-(4-methoxyphenylmethyl)-9H-purine
  参考文献：
  名称：

  6-(2-Furanyl)-9H-purin-2-amine derivatives as A2A adenosine antagonists

  摘要：

  Structure-activity relationships have been investigated through substitutions at the 9-position of the 2-amino-6-(2-furanyl) purine (5) to identify novel and selective A(2A) adenosine receptor antagonists. Several potent and selective antagonists were identified. In particular, compounds 20, 25, and 26 show very high affinity with excellent selectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.031

文献信息

• Purine derivatives as purinergic receptor antagonists
  申请人：Gillespie John Roger

  公开号：US20060270691A1

  公开（公告）日：2006-11-30

  Use of a compound of formula (I) wherein R 1 is selected from alkyl, aryl, alkoxy, aryloxy, 0thioalkyl, thioaryl, CN, halo, NR 5 R 6 , NR 4 COR 5 , NR 4 CONR 5 R 6 , NR 4 CO 2 R 7 and NR 4 SO 2 R 7 ; R 2 is selected from N, O or S-containing heteroaryl groups, wherein the heteroaryl group is attached via an unsaturated carbon atom which is adjacent to one or two N, O or S-heteroatom(s), other than ortho, ortho-disubstituted heteroaryl groups; R 3 is selected from H, alkyl, COR 8 , CONR 9 R 10 , CONR 8 NR 9 R 10 , CO 2 R 11 and SO 2 R 11 ; R 4 , R 5 and R 6 are independently selected from H, alkyl and aryl or where R 5 and R 6 are in an (NR 5 R 6 ) group then R 5 and R 6 may be linked to form a heterocyclic ring; R 7 is selected from alkyl and aryl; R 8 , R 9 and R 10 are independently selected from H, alkyl and aryl, or R 9 and R 10 may be linked to form a heterocyclic ring, or where R 8 , R 9 and R 10 are in a (CONR 8 NR 9 R 10 ) group, R 8 and R 9 may be linked to form a heterocyclic group; and R 1 is selected from alkyl and aryl, or a pharmaceutically acceptable salt thereof or prodrug thereof, in the treatment or prevention of a disorder in which the blocking of purine receptors, particularly adenosine receptors and more particularly A 2A receptors, may be beneficial, particularly wherein said disorder is a movement disorder such as Parkinson's disease or said disorder is depression, cognitive or memory impairment, acute or chronic pain, ADHD or narcolepsy, or for neuroprotection in a subject; compounds of formula (I) for use in therapy; and novel compounds of formula (I) per se.

  使用公式（I）的化合物，其中R1选自烷基，芳基，烷氧基，芳氧基，0硫代烷基，硫代芳基，CN，卤素，NR5R6，NR4COR5，NR4CONR5R6，NR4CO2R7和NR4SO2R7; R2选自含N，O或S的杂环芳基基团，其中杂环芳基基团通过与一个或两个N，O或S杂原子相邻的不饱和碳原子连接，但不包括邻位或邻位二取代的杂环芳基基团; R3选自H，烷基，COR8，CONR9R10，CONR8NR9R10，CO2R11和SO2R11; R4，R5和R6独立地选自H，烷基和芳基，或者当R5和R6在（NR5R6）组中时，R5和R6可以连接形成杂环环; R7选自烷基和芳基; R8，R9和R10独立地选自H，烷基和芳基，或者R9和R10可以连接形成杂环环，或者当R8，R9和R10在（CONR8NR9R10）组中时，R8和R9可以连接形成杂环基团; R1选自烷基和芳基，或其药学上可接受的盐或前药，在治疗或预防封闭嘌呤受体（特别是腺苷受体，尤其是A2A受体）可能有益的疾病中，特别是其中所述疾病是运动障碍，如帕金森病，或所述疾病是抑郁症，认知或记忆障碍，急性或慢性疼痛，ADHD或嗜睡症，或用于对受试者进行神经保护; 公式（I）的化合物用于治疗; 以及公式（I）的新化合物本身。
• 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.
• PURINE DERIVATIVES AS PURINERGIC RECEPTOR ANTAGONISTS
  申请人：VERNALIS RESEARCH LIMITED

  公开号：EP1349857B1

  公开（公告）日：2010-06-16
• US7452894B2
  申请人：——

  公开号：US7452894B2

  公开（公告）日：2008-11-18
• 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。