1,3-二乙基-8-苯基黄嘌呤 | 75922-48-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 1,3-二乙基-8-苯基黄嘌呤
• 英文名称: 1,3-diethyl-8-phenylxanthine
• 英文别名: 8-phenyl-1,3-diethylxanthine；DPX；1,3-diethyl-8-phenyl-1H-purine-2,6(3H,7H)-dione；8-phenyl-1,3,-diethylxanthine；1,3-diethyl-8-phenyl-7H-purine-2,6-dione
• CAS: 75922-48-4
• 化学式: C₁₅H₁₆N₄O₂
• mdl: MFCD00043206
• 分子量: 284.318
• InChiKey: LVSWNSHUTPWCNF-UHFFFAOYSA-N

物化性质

• 熔点：
  298-300°C
• 沸点：
  426.81°C (rough estimate)
• 密度：
  1.1455 (rough estimate)
• 溶解度：
  H2O：极微溶

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.266
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  1,3-二乙基-8-苯基黄嘌呤 在 tetraphosphorus decasulfide 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以72%的产率得到1,3-Diethyl-8-phenyl-6-thioxo-1,3,6,7-tetrahydro-purin-2-one
  参考文献：
  名称：

  Sulfur-containing 1,3-dialkylxanthine derivatives as selective antagonists at A1-adenosine receptors

  摘要：

  Sulfur-containing analogues of 8-substituted xanthines were prepared in an effort to increase selectivity or potency as antagonists at adenosine receptors. Either cyclopentyl or various aryl substituents were utilized at the 8-position, because of the association of these groups with high potency at A1-adenosine receptors. Sulfur was incorporated on the purine ring at positions 2 and/or 6, in the 8-position substituent in the form of 2- or 3-thienyl groups, or via thienyl groups separated from an 8-aryl substituent through an amide-containing chain. The feasibility of using the thienyl group as a prosthetic group for selective iodination via its Hg2+ derivative was explored. Receptor selectivity was determined in binding assays using membrane homogenates from rat cortex [( 3H]-N6-(phenylisopropyl)adenosine as radioligand] or striatum [3H]-5'-(N-ethylcarbamoyl)adenosine as radioligand] for A1- and A2-adenosine receptors, respectively. Generally, 2-thio-8-cycloalkylxanthines were at least as A1 selective as the corresponding oxygen analogue. 2-Thio-8-aryl derivatives tended to be more potent at A2 receptors than the oxygen analogue. 8-[4-[(Carboxy-methyl)oxyl] phenyl]-1,3-dipropyl-2-thioxanthine ethyl ester was greater than 740-fold A1 selective.

  DOI：

  10.1021/jm00128a031
• 作为产物：
  描述：

  1,3-二乙基-5,6-二氨基尿嘧啶 、 苯甲醛 在 溴化二甲基溴化锍 作用下， 以 乙腈 为溶剂， 以70%的产率得到1,3-二乙基-8-苯基黄嘌呤
  参考文献：
  名称：

  通过5，6-二氨基尿嘧啶合成8取代的黄嘌呤：一种有效的途径到A 2A腺苷受体拮抗剂

  摘要：

  由5，6-二氨基尿嘧啶和羧醛开发了一种一锅法制备8-取代的黄嘌呤的方法。由（溴二甲基）溴化promote促进的该方法温和有效，并且不需要外部氧化剂。收率良好，并且该方法适用于多种底物，包括A 2A腺苷受体拮抗剂家族。介绍了拮抗剂KW-6002的新类似物的制备，并证明了芳基取代产物的原位溴化。

  DOI：

  10.1016/j.tetlet.2008.05.071

文献信息

• Synthesis of 8-substituted xanthines via 5,6-diaminouracils: an efficient route to A2A adenosine receptor antagonists
  作者：Ma Dong、Mikhail Sitkovsky、Amy E. Kallmerten、Graham B. Jones

  DOI：10.1016/j.tetlet.2008.05.071

  日期：2008.7

  A one-pot route to 8-substituted xanthines has been developed from 5,6-diaminouracils and carboxaldehydes. The process, promoted by (bromodimethyl)sulfonium bromide, is mild and efficient and eliminates the need for external oxidants. Yields are good and the process is applicable to a range of substrates including a family of A2A adenosine receptor antagonists. Preparation of a new analog of the antagonist

  由5，6-二氨基尿嘧啶和羧醛开发了一种一锅法制备8-取代的黄嘌呤的方法。由（溴二甲基）溴化promote促进的该方法温和有效，并且不需要外部氧化剂。收率良好，并且该方法适用于多种底物，包括A 2A腺苷受体拮抗剂家族。介绍了拮抗剂KW-6002的新类似物的制备，并证明了芳基取代产物的原位溴化。
• 2-Aminopyridine compounds and use thereof as drugs
  申请人：——

  公开号：US20040006082A1

  公开（公告）日：2004-01-08

  The present invention provides 2-aminopyridine compound having an excellent adenosine receptor (A 1 , A 2a , A 2b receptors) antagonism, which is represented by the following formula: 1 (wherein, R 1 represents cyano group, carboxyl group or an optionally substituted carbamoyl group; R 2 represents hydrogen atom, hydroxyl group, an optionally substituted C 1-6 alkoxy group, an optionally substituted C 6-14 aromatic hydrocarbon cyclic group or an optionally substituted 5- to 14-membered aromatic heterocyclic group; and R 3 and R 4 are the same as or different from each other and each represents a C 6-14 aromatic hydrocarbon cyclic group, a 5- to 14-membered non-aromatic heterocyclic group or a 5- to 14-membered aromatic heterocyclic group which may be substituted, respectively) or a salt thereof.

  本发明提供了一种具有优异腺苷受体（A1、A2a、A2b 受体）拮抗作用的 2-氨基吡啶化合物，其化学式如下：1（其中，R1代表氰基、羧基或可选择取代的氨基甲酰基；R2代表氢原子、羟基、可选择取代的C1-6烷氧基、可选择取代的C6-14芳香烃环基或可选择取代的 5-到 14-成员芳香杂环基；R3和 R4相同或不同，分别代表 C6-14芳香烃环基、 5-到 14-成员非芳香杂环基或可选择取代的 5-到 14-成员芳香杂环基，或其盐。
• Medicinal compositions promoting bowel movement
  申请人：——

  公开号：US20030171383A1

  公开（公告）日：2003-09-11

  The present invention provides a medicament having a gentle but strong defecation-promoting action without causing diarrhea. That is, it provides a defecation-promoting agent comprising a compound having an adenosine A 2 receptor antagonism, preferably an adenosine A 2b receptor antagonism, or a salt thereof.

  本发明提供了一种药物，具有温和而强效的促进排便作用，而不会引起腹泻。也就是说，提供了一种促进排便的药剂，包括一种具有腺苷A2受体拮抗作用的化合物，最好是腺苷A2B受体拮抗作用，或其盐。
• Dopamine analog amide
  申请人：——

  公开号：US20010056116A1

  公开（公告）日：2001-12-27

  The invention involves the formation of a prodrug from a fatty acid carrier and a neuroactive drug. The prodrug is stable in the environment of both the stomach and the bloodstream and may be delivered by ingestion. The prodrug passes readily through the blood brain barrier. Once in the central nervous system, the prodrug is hydrolyzed into the fatty acid carrier and the drug to release the drug. In a preferred embodiment, the carrier is 4, 7, 10, 13, 16, 19 docosahexa-enoic acid and the drug is dopamine. Both are normal components of the central nervous system. The covalent bond between the drug and the carrier preferably is an amide bond, which bond may survive the conditions in the stomach. Thus, the prodrug may be ingested and will not be hydrolyzed completely into the carrier molecule and drug molecule in the stomach.

  该发明涉及使用脂肪酸载体和神经活性药物形成前药。该前药在胃和血液流动环境中稳定，并可通过口服递送。该前药容易穿过血脑屏障。一旦进入中枢神经系统，前药被水解成脂肪酸载体和药物以释放药物。在首选实施方式中，载体是4,7,10,13,16,19二十二碳六烯酸，药物是多巴胺。两者都是中枢神经系统的正常成分。药物和载体之间的共价键通常是酰胺键，这种键可以在胃的条件下存活。因此，前药可以被摄入，并且不会在胃中完全水解成载体分子和药物分子。
• Pyrimidone compounds and pharmaceutical compositions containing the same
  申请人：——

  公开号：US20040259865A1

  公开（公告）日：2004-12-23

  The present invention provides a medicament having a gentle but strong defecation-promoting action without causing diarrhea. That is, it provides a defecation-promoting agent comprising a compound having an adenosine A 2 receptor antagonism, preferably an adenosine A 2b receptor antagonism, or a salt thereof.

  本发明提供了一种药物，具有温和但强效的促进排便作用，而不会引起腹泻。也就是说，它提供了一种促进排便的药剂，包括具有腺苷A2受体拮抗作用的化合物，优选为腺苷A2b受体拮抗剂或其盐。