3,7-二氢-1,3-二丙基-7-(2-丙炔-1-基)-1H-嘌呤-2,6-二酮 | 102284-70-8

• 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: 3,7-二氢-1,3-二丙基-7-(2-丙炔-1-基)-1H-嘌呤-2,6-二酮
• 中文别名: 7-(2-丙炔-1-基)-1,3-二丙基-1H-嘌呤-2,6(3h,7h)-二酮；1,3-N-二丙基-7-炔丙基黄嘌呤
• 英文名称: 7-propargyl-1,3-dipropylxanthine
• 英文别名: 7-(Prop-2-yn-1-yl)-1,3-dipropyl-1H-purine-2,6(3H,7H)-dione；1,3-dipropyl-7-prop-2-ynylpurine-2,6-dione
• CAS: 102284-70-8
• 化学式: C₁₄H₁₈N₄O₂
• 分子量: 274.323
• InChiKey: ZJNGTKZTSFZGPQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.19

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3,7-二氢-1,3-二丙基-7-(2-丙炔-1-基)-1H-嘌呤-2,6-二酮 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以58%的产率得到1,3,7-三丙基黄嘌呤
  参考文献：
  名称：

  Analogs of caffeine and theophylline: effect of structural alterations on affinity at adenosine receptors

  摘要：

  A variety of analogues of caffeine and theophylline in which the 1-,3-, and 7-methyl substituents have been replaced with n-propyl, allyl, propargyl, and isobutyl and, in a few cases, with chloroethyl, hydroxyethyl, or benzyl were assessed for potency and selectivity as antagonists at A1- and A2-adenosine receptors in brain tissue. Caffeine and theophylline are nonselective for these receptors. Nearly all of the 22 analogues of caffeine are more potent than caffeine itself at adenosine receptors. Replacement of the 1-methyl moiety with n-propyl, allyl, or propargyl substituent has little effect on potency at the A1 receptor while enhancing potency about 7- to 10-fold at the A2 receptor. 3,7-Di-methyl-1-propylxanthine is only slightly (1.4-fold) more potent than caffeine at the A1 receptor while being 10-fold more potent at the A2 receptor. 1,3-Di-n-propyl-7-methylxanthine is also selective for the A2 receptor, being 8-fold more potent than caffeine at the A1 receptor and 40-fold more potent at the A2 receptor. A number of other caffeine analogues including 3,7-dimethyl-1-n-propylxanthine, 7-allyl-1,3-dimethylxanthine, and 1,3-dimethyl-7-propargylxanthine are also somewhat selective for the A2 receptor. The most potent caffeine analogue was 1,3-di-n-propyl-7-propargylxanthine, which was about 100-fold more potent than caffeine at both A1 and A2 receptors. The 10 theophylline analogues were relatively nonselective except for the 1-ethyl analogue and the 1,3-diallyl analogue, which were selective for the A2 receptor, and the 1,3-di-n-propyl, 1,3-diisobutyl, and 1,3-dibenzyl analogues, which were somewhat selective for the A1 receptor. 1,3-Di-n-propylxanthine was 20-fold more potent than theophylline at the A1 receptor and 5-fold more potent at the A2 receptor.

  DOI：

  10.1021/jm00157a035
• 作为产物：
  描述：

  3,9-二氢-1,3-二丙基-1H-嘌呤-2,6-二酮 、 3-溴丙炔 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以71%的产率得到3,7-二氢-1,3-二丙基-7-(2-丙炔-1-基)-1H-嘌呤-2,6-二酮
  参考文献：
  名称：

  Analogs of caffeine and theophylline: effect of structural alterations on affinity at adenosine receptors

  摘要：

  A variety of analogues of caffeine and theophylline in which the 1-,3-, and 7-methyl substituents have been replaced with n-propyl, allyl, propargyl, and isobutyl and, in a few cases, with chloroethyl, hydroxyethyl, or benzyl were assessed for potency and selectivity as antagonists at A1- and A2-adenosine receptors in brain tissue. Caffeine and theophylline are nonselective for these receptors. Nearly all of the 22 analogues of caffeine are more potent than caffeine itself at adenosine receptors. Replacement of the 1-methyl moiety with n-propyl, allyl, or propargyl substituent has little effect on potency at the A1 receptor while enhancing potency about 7- to 10-fold at the A2 receptor. 3,7-Di-methyl-1-propylxanthine is only slightly (1.4-fold) more potent than caffeine at the A1 receptor while being 10-fold more potent at the A2 receptor. 1,3-Di-n-propyl-7-methylxanthine is also selective for the A2 receptor, being 8-fold more potent than caffeine at the A1 receptor and 40-fold more potent at the A2 receptor. A number of other caffeine analogues including 3,7-dimethyl-1-n-propylxanthine, 7-allyl-1,3-dimethylxanthine, and 1,3-dimethyl-7-propargylxanthine are also somewhat selective for the A2 receptor. The most potent caffeine analogue was 1,3-di-n-propyl-7-propargylxanthine, which was about 100-fold more potent than caffeine at both A1 and A2 receptors. The 10 theophylline analogues were relatively nonselective except for the 1-ethyl analogue and the 1,3-diallyl analogue, which were selective for the A2 receptor, and the 1,3-di-n-propyl, 1,3-diisobutyl, and 1,3-dibenzyl analogues, which were somewhat selective for the A1 receptor. 1,3-Di-n-propylxanthine was 20-fold more potent than theophylline at the A1 receptor and 5-fold more potent at the A2 receptor.

  DOI：

  10.1021/jm00157a035

文献信息

• Stable Aqueous Compositions Comprising Amide-Protected Bioactive Creatine Species and Uses Thereof
  申请人：Owoc John H.

  公开号：US20110251280A1

  公开（公告）日：2011-10-13

  The present invention provides amide-protected creatine molecules and compositions, containing one or more bioactive forms of creatine in aqueous compositions, wherein bioactive forms of creatine do not appreciably degrade into creatinine. Also provided are various beneficial effects of administering aqueous compositions having at least one amide-protected creatine molecule.

  本发明提供了酰胺保护的肌酸分子和组合物，其中含有一种或多种生物活性形式的肌酸在水性组合物中，其中生物活性形式的肌酸不会明显降解为肌酸酐。还提供了在至少含有一种酰胺保护的肌酸分子的水性组合物中施用的各种有益效果。
• SYNERGISTIC ANTI-INFLAMMATORY PHARMACEUTICAL COMPOSITIONS AND RELATED METHODS USING CURCUMINOIDS OR METHYLXANTHINES
  申请人：Metaproteomics, LLC

  公开号：EP1718312A2

  公开（公告）日：2006-11-08
• Pharmaceutical compositions comprising hops extract derivatives and caffeine
  申请人：Metaproteomics, LLC

  公开号：EP1718312B1

  公开（公告）日：2015-03-25
• EP2338481A2
  申请人：——

  公开号：EP2338481A2

  公开（公告）日：2011-06-29
• Synergistic anti-inflammatory pharmaceutical compositions and related methods using curcuminoids or methylxanthines
  申请人：Babish G. John

  公开号：US20050191375A1

  公开（公告）日：2005-09-01

  The invention provides compositions containing a fraction isolated or derived from hops and a methylxanthine. The invention additionally provides compositions containing a fraction derived from hops and a curcuminoid. The invention also provides methods of using such compositions to reduce inflammation.