1,3-Diallylxanthine | 31542-64-0

• 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: 1,3-Diallylxanthine
• 英文别名: 1,3-di(2-propenyl)xanthine；1H-Purine-2,6-dione, 3,9-dihydro-1,3-di-2-propen-1-yl-；1,3-bis(prop-2-enyl)-7H-purine-2,6-dione
• CAS: 31542-64-0
• 化学式: C₁₁H₁₂N₄O₂
• 分子量: 232.242
• InChiKey: NUZFZZOVBJUJQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-Diallylxanthine 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以68%的产率得到1,3-二烯丙基-7-甲基黄嘌呤
  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：

  1,3-二烯丙基-5,6-二氨基尿苷盐酸 在 sodium hydroxide 作用下， 反应 1.5h， 生成 1,3-Diallylxanthine
  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

• DENDRIMER CONJUGATES OF AGONISTS AND ANTAGONISTS OF THE GPCR SUPERFAMILY
  申请人：Jacobson Kenneth A.

  公开号：US20090012035A1

  公开（公告）日：2009-01-08

  Disclosed are conjugates comprising a dendrimer and a ligand, which is a functionalized congener of an agonist or antagonist of a receptor of the G-protein coupled receptor (GPCR) superfamily, for example, wherein the functionalized congener is an A 1 adenosine receptor agonist having a purine nucleoside moiety and a functional group at the N 6 position of the purine nucleoside moiety, wherein the functional group has the formula (I): N 6 H—Ar 1 —CH 2 —C(═O)NH—R 1 (I), wherein Ar 1 and R 1 as defined herein. Also disclosed are pharmaceutical compositions, methods of treating various diseases, and a diagnostic method employing such conjugates.

  本文披露了包含树状聚合物和配体的共轭物，其中配体是G-蛋白偶联受体（GPCR）超家族受体的激动剂或拮抗剂的官能化同系物，例如，其中官能化同系物是具有嘌呤核苷酸基团和在嘌呤核苷酸基团的N6位置上具有官能基的A1腺苷受体激动剂，其中官能基具有以下结构式（I）：N6H—Ar1—CH2—C(═O)NH—R1（I），其中Ar1和R1如本文所定义。还披露了包括制药组合物、治疗各种疾病的方法以及使用这种共轭物的诊断方法。
• Use of xanthine derivatives for reducing the pathological hyperreactivity of eosinophilic granulocytes, novel xanthine compounds and process for their preparation
  申请人：Hoechst Aktiengesellschaft

  公开号：US20020010333A1

  公开（公告）日：2002-01-24

  Use of xanthine derivatives for reducing the pathological hyperreactivity of eosinophilic granulocytes, novel xanthine compounds and process for their preparation. Tertiary 1-(hydroxyalkyl)-4-alkylxanthines are suitable for the production of pharmaceuticals for the treatment of disorders which is associated with a pathologically increased reactivity of eosinophilic granulocytes. Novel xanthine derivatives and process for their preparation are described.

  黄嘌呤衍生物的使用可降低嗜酸性粒细胞的病理性高反应性，新型黄嘌呤化合物及其制备方法。三级1-(羟基烷基)-4-烷基黄嘌呤适用于生产用于治疗与嗜酸性粒细胞病理性增强反应性相关的疾病的药物。描述了新型黄嘌呤衍生物及其制备方法。
• [EN] NOVEL A1 ADENOSINE RECEPTOR AGONISTS AND ANTIAGONISTS<br/>[FR] NOUVEAUX AGONISTES ET ANTAGONISTES DE RECEPTEURS DE L'ADENOSINE A1
  申请人：UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INC.

  公开号：WO1995011904A1

  公开（公告）日：1995-05-04

  (EN) Adenosine and xanthine derivatives, and compositions comprising those compounds, are potent selective agonists and antagonists of adenosine receptors. The derivatives and compositions are used to treat conditions, including certain cardiac arrhythmias.(FR) On décrit des dérivés d'adénosines et de xanthines, qui sont de puissants agonistes et antagonistes sélectifs de récepteurs d'une adénosine, ainsi que des compositions contenant ces composés. On utilise ces dérivés et compositions pour traiter des pathologies telles que certaines arythmies cardiaques.

  (中文) 腺苷和黄嘌呤衍生物，以及含有这些化合物的组合物，是腺苷受体的强效选择性激动剂和拮抗剂。这些衍生物和组合物用于治疗包括某些心律失常在内的疾病。
• Low glycemic response compositions
  申请人：The Procter & Gamble Co.

  公开号：US20020187219A1

  公开（公告）日：2002-12-12

  The present disclosure is related to compositions useful in the field of foods and beverages. In particular, the present invention relates to those compositions that reduce the postprandial rise in blood glucose (described as low Glycemic Index) that synergistically provide enhanced metabolism in the mammalian system and inhibit the storage of systemic fat. In particular, the present invention relates to compositions comprising: a) one or more flavanols; b) one or more bracers; and c) vitamin B; wherein the composition exhibits a Glycemic Index of about 55 or less. As disclosed, the unique combination of ingredients, which provide the defined, low Glycemic Index, work synergistically together to enhance perception of energy and/or improve physiological energy via metabolism enhancement over a long duration of time, without resulting in sudden peaks of glucose in the mammalian system. Thus, the present compositions effectively modulate glucose in the system, thereby providing energy to the system without resulting in the storage of systemic fat.

  本公开涉及在食品和饮料领域有用的组合物。特别是，本发明涉及那些能够减少餐后血糖上升（描述为低升糖指数）的组合物，这些组合物在哺乳动物系统中协同作用，提供增强的代谢作用并抑制系统性脂肪的储存。特别是，本发明涉及包括：a）一种或多种黄烷醇；b）一种或多种支链氨基酸；和c）维生素B的组合物；其中该组合物表现出约55或更低的升糖指数。如本文所述，这些独特的成分组合，以定义的低升糖指数为特征，协同作用，能够提高能量感知和/或通过代谢增强长时间改善生理能量，而不会导致哺乳动物系统中的血糖突然峰值。因此，本组合物有效地调节系统中的葡萄糖，从而为系统提供能量而不导致系统性脂肪的储存。
• Compositions, kits, and methods for promoting defined health benefits
  申请人：——

  公开号：US20030069202A1

  公开（公告）日：2003-04-10

  The present invention is directed to compositions comprising: (a) a first component selected from the group consisting of gelatin, cartilage, aminosugars, glycosaminoglycans, methylsulfonylmethane, precursors of methylsulfonylmethane, S-adenosylmethionine, salts thereof, and mixtures thereof; and (b) a second component comprising: (i) a cation source selected from the group consisting of calcium, potassium, magnesium, and mixtures thereof; and (ii) an edible acid source. The present invention is further directed to food, beverage, pharmaceutical, over-the- counter, and dietary supplement products, which comprise the present compositions. The invention also relates to kits comprising the present compositions and information that use of the composition promotes one or more of the presently defined health benefits, including joint health, bone health, cardiac health, and anti-inflammation. The present invention additionally relates to methods of treating joint function, bone function, cardiac function, or inflammation comprising administering to a mammal a composition as defined herein.

  本发明涉及包括以下组分的组合物：(a)从明胶、软骨、氨基糖、糖胶质、甲基磺酰甲烷、甲基磺酰甲烷的前体、S-腺苷甲硫氨酸、其盐和其混合物中选择的第一组分; 和(b)包括：(i)从钙、钾、镁和其混合物中选择的阳离子源; 和(ii)可食用的酸源的第二组分。本发明还涉及包含本组合物的食品、饮料、制药、非处方药和膳食补充剂产品。本发明还涉及包含本组合物和使用该组合物促进当前定义的健康益处之一或多个的信息的套件。本发明还涉及治疗关节功能、骨功能、心脏功能或炎症的方法，包括向哺乳动物投与本文所定义的组合物。