1,3-dipropyl-8-(2-furanyl)xanthine | 117027-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 1,3-dipropyl-8-(2-furanyl)xanthine
• 英文别名: 1,3-dipropyl-8-furanylxanthine；8-(furan-2-yl)-1,3-dipropyl-7H-purine-2,6-dione
• CAS: 117027-86-8
• 化学式: C₁₅H₁₈N₄O₃
• 分子量: 302.333
• InChiKey: XJBFUWXRIXHYGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-dipropyl-8-(2-furanyl)xanthine 在 镍 氢气 作用下， 以 甲醇 为溶剂， 100.0 ℃ 、183.84 MPa 条件下， 以to yield 0.34 g of the 1,3-dipropyl-8-(2-tetrahydrofuranyl)xanthine as a white solid, mp 155°-8° C.的产率得到1,3-dipropyl-8-(2-tetrahydrofuranyl) xanthine
  参考文献：
  名称：

  Derivatives of xanthine, pharmaceutical compositions and methods of use

  摘要：

  本发明是黄嘌呤的新型双取代衍生物，以及其药物组合物和使用方法。该新型黄嘌呤的活性特别包括认知活化。

  公开号：

  US04755517A1
• 作为产物：
  描述：

  5,6-二氨基-1,3-二丙基嘧啶-2,4(1H,3H)-二酮 在 吡啶 、 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 11.0h， 生成 1,3-dipropyl-8-(2-furanyl)xanthine
  参考文献：
  名称：

  8-Polycycloalkyl-1,3-dipropylxanthines as potent and selective antagonists for A1-adenosine receptors

  摘要：

  With the aim of characterizing the hydrophobic interactions between xanthines and the A1 receptor site, 1,3-dipropyl-8-substituted xanthines were synthesized. Introduction of a quaternary carbon and the conformationally restricted cyclopentyl moiety into the 8-position of xanthines enhanced the adenosine A1 antagonism. 1,3-Dipropyl-8-(3-noradamantyl)xanthine (42) was identified to be a selective and the most potent A1 receptor antagonist reported to date. Under our structure-activity relationship, the 8-substituent of xanthine antagonists and the N6-substituent of adenosine agonists appears to bind to the same region of the A1 receptor.

  DOI：

  10.1021/jm00083a018

文献信息

• Neue Xanthinderivate mit Adenosin-antagonistischer Wirkung
  申请人：BOEHRINGER INGELHEIM KG

  公开号：EP0374808A2

  公开（公告）日：1990-06-27

  Die Erfindung betrifft neue Xanthinderivate der allgemeinen Formel I, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel.

  本发明涉及通式 I 的新黄嘌呤衍生物、其制备工艺及其作为药物的用途。
• Sulfur-containing 1,3-dialkylxanthine derivatives as selective antagonists at A1-adenosine receptors
  作者：Kenneth A. Jacobson、Leonidas Kiriasis、Suzanne Barone、Barton J. Bradbury、Udai Kammula、Jean Michel Campagne、John W. Daly、John L. Neumeyer、Wolfgang Pfleiderer、Sherrie Secunda

  DOI：10.1021/jm00128a031

  日期：1989.8

  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.
• KUFNER-MUHL, ULRIKE;WEBER, KARL-HEINZ;WALTHER, GERHARD;STRANSKY, WERNER;E+
  作者：KUFNER-MUHL, ULRIKE、WEBER, KARL-HEINZ、WALTHER, GERHARD、STRANSKY, WERNER、E+

  DOI：——

  日期：——
• BRUNS, ROBERT F.;HAMILTON, HARRIET W.
  作者：BRUNS, ROBERT F.、HAMILTON, HARRIET W.

  DOI：——

  日期：——
• US4755517A
  申请人：——

  公开号：US4755517A

  公开（公告）日：1988-07-05