1,3-dipropyl-8-(3-hydroxycyclopentyl)xanthine | 133058-47-6

• 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-(3-hydroxycyclopentyl)xanthine
• 英文别名: 8-(3-hydroxycyclopentyl)-1,3-dipropylxanthine；1,3-Dipropyl-8-[3-hydroxycyclopentyl]xanthine；1,3-Dipropyl-8-(1-hydroxycyclopent-3-yl)xanthine；8-(3-hydroxycyclopentyl)-1,3-dipropyl-7H-purine-2,6-dione
• CAS: 133058-47-6
• 化学式: C₁₆H₂₄N₄O₃
• 分子量: 320.392
• InChiKey: NRECPLZNMXAXRH-UHFFFAOYSA-N

物化性质

• 熔点：
  174-176 °C
• 沸点：
  583.3±60.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  89.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(氟磺酰基)苯甲酰氯 、 1,3-dipropyl-8-(3-hydroxycyclopentyl)xanthine 在 二甲基十二/十四烷基叔胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以58%的产率得到3-Fluorosulfonyl-benzoic acid 3-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-cyclopentyl ester
  参考文献：
  名称：

  Substituted 1,3-Dipropylxanthines as Irreversible Antagonists of A1 Adenosine Receptors

  摘要：

  This report describes the synthesis of 29 xanthines containing a chemoreactive chloroaryl beta-chloroethylamino, alpha,beta-unsaturated carbonyl bromoacetyl, 3-(fluorosulfonyl)benzoyl, or 4-(fluorosulfonyl)benzoyl group as part of an exocyclic 1-, 3-, or 8-substituent. The xanthines inhibited the binding of [H-3]-8-cyclopentyl-1,3-dipropylxanthine ([H-3]CPX) to the A(1) adenosine receptor (A(1)AR) of DDT1 MF2 cells at IC(50)s in the low-nanomolar to low-micromolar range. Seven of the 29 analogues irreversibly inhibited the binding of [H-3]CPX without changing the K-D of that ligand; five were 1,3-dipropylxantines having the following reactive groups as 8-substituents: (bromoacetamido)methyl (24), (bromoacetamido)ethyl (25), (bromoacetamido)propyl (26), [4-(fluorosulfonyl)benzamido]methyl (33) or 3-[[4-(fluorosulfonyl)benzoyl]oxy]cyclopentyl (42). Both 8-cyclopentyl-3-[3-[[4-(fluorosulfonyl)benzoyl]oxy]propyl]-1-propylxanthine (53) and 8-cyclopentyl-3-bis[3-[[4-(fluorosulfonyl)benzoyl]oxy]propyl]xanthine (55) inhibited [H-3]CPX binding irreversibly. Five of the ligands, including 26, 33 (IC50 = 49 mu M), and 53 (IC50 = 9 mu M), antagonized the binding of [H-3]NECA to the A(2a)AR of PC12 cells, but unlike binding to the A(1)AR, binding to the A(2a)AR was completely reversible. The potency of 33 (IC50 = 2 mu M, 72% loss of CPX binding at 1 mu M) and 53 (IC50 - 0.01 mu M, 74% loss of CPX binding at 0.05 mu M) and their seletivity for the A(1)AR suggest that those two ligands may be useful in studies of the structure and function of that receptor.

  DOI：

  10.1021/jm00043a010
• 作为产物：
  描述：

  8-(3-cyclopenten-1-yl)-1,3-dipropylxanthine 在 sodium hydroxide 、 硼烷四氢呋喃络合物 、 双氧水 作用下， 生成 1,3-dipropyl-8-(3-hydroxycyclopentyl)xanthine
  参考文献：
  名称：

  Substituted 1,3-Dipropylxanthines as Irreversible Antagonists of A1 Adenosine Receptors

  摘要：

  This report describes the synthesis of 29 xanthines containing a chemoreactive chloroaryl beta-chloroethylamino, alpha,beta-unsaturated carbonyl bromoacetyl, 3-(fluorosulfonyl)benzoyl, or 4-(fluorosulfonyl)benzoyl group as part of an exocyclic 1-, 3-, or 8-substituent. The xanthines inhibited the binding of [H-3]-8-cyclopentyl-1,3-dipropylxanthine ([H-3]CPX) to the A(1) adenosine receptor (A(1)AR) of DDT1 MF2 cells at IC(50)s in the low-nanomolar to low-micromolar range. Seven of the 29 analogues irreversibly inhibited the binding of [H-3]CPX without changing the K-D of that ligand; five were 1,3-dipropylxantines having the following reactive groups as 8-substituents: (bromoacetamido)methyl (24), (bromoacetamido)ethyl (25), (bromoacetamido)propyl (26), [4-(fluorosulfonyl)benzamido]methyl (33) or 3-[[4-(fluorosulfonyl)benzoyl]oxy]cyclopentyl (42). Both 8-cyclopentyl-3-[3-[[4-(fluorosulfonyl)benzoyl]oxy]propyl]-1-propylxanthine (53) and 8-cyclopentyl-3-bis[3-[[4-(fluorosulfonyl)benzoyl]oxy]propyl]xanthine (55) inhibited [H-3]CPX binding irreversibly. Five of the ligands, including 26, 33 (IC50 = 49 mu M), and 53 (IC50 = 9 mu M), antagonized the binding of [H-3]NECA to the A(2a)AR of PC12 cells, but unlike binding to the A(1)AR, binding to the A(2a)AR was completely reversible. The potency of 33 (IC50 = 2 mu M, 72% loss of CPX binding at 1 mu M) and 53 (IC50 - 0.01 mu M, 74% loss of CPX binding at 0.05 mu M) and their seletivity for the A(1)AR suggest that those two ligands may be useful in studies of the structure and function of that receptor.

  DOI：

  10.1021/jm00043a010
• 作为试剂：
  描述：

  8-(3-氧代环戊基)-1,3-二丙基-7H-嘌呤-2,6-二酮 、 在 水 、 二氯甲烷 、 silica gel 、 1,3-dipropyl-8-(3-hydroxycyclopentyl)xanthine 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以From the 1st fraction, 0.4 g of the title compound are obtained in the form of white crystals (39% of theory), m.p. 174°-176° C. and from the 2nd fraction 0.4 g of the title compound的产率得到1,3-dipropyl-8-(3-hydroxycyclopentyl)xanthine
  参考文献：
  名称：

  Xanthine derivatives with adenosine-antagonistic activity

  摘要：

  本发明涉及一种新的黄嘌呤衍生物，其通式为I，以及制备它们和将它们用作药物组成物的方法。

  公开号：

  US05696124A1

文献信息

• 8-(oxo-substituted cycloalkyl)xanthines
  申请人：Marion Merrell Dow Inc.

  公开号：US05175290A1

  公开（公告）日：1992-12-29

  1,3-Substituted-8-(oxo-substituted cycloalkyl)xanthines and pharmaceutically acceptable salts of such compounds are disclosed. Preferred compounds include the cis and trans isomers of 1,3-dipropyl-8-(3-hydroxycyclopentyl)xanthine and the cis and trans isomers of 1,3-dipropyl-8-(4-hydroxycyclohexyl)xanthine. The compounds are potent and selective bronchodilators and/or cardiotonic agents.

  本文介绍了1,3-取代-8-(氧代取代环烷基)黄嘌呤及其药物可接受的盐。首选化合物包括1,3-二丙基-8-(3-羟基环戊基)黄嘌呤的顺反异构体和1,3-二丙基-8-(4-羟基环己基)黄嘌呤的顺反异构体。这些化合物是有效且选择性的支气管扩张剂和/或心力增强剂。
• Process for preparing 1,3-dipropyl-8-(3-oxocyclopentyl)-xanthine
  申请人：Boehringer Ingelheim KG

  公开号：US05175291A1

  公开（公告）日：1992-12-29

  A process for preparing 1,3-dipropyl-8-(3-oxocyclopentyl)-xanthine.

  一种制备1,3-二丙基-8-(3-氧代环戊基)-黄嘌呤的过程。
• Bornyl xanthine derivatives with adenosine-antagonistic activity
  申请人：Boehringer Ingelheim KG

  公开号：US05688802A1

  公开（公告）日：1997-11-18

  The invention relates to new xanthine derivatives of general formula I, processes for preparing them and their use as pharmaceutical compositions.

  本发明涉及一种新的黄嘌呤衍生物，其通式为I，以及制备它们和将它们用作药物组成物的方法。
• 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。
• [DE] XANTHINDERIVATE ALS DIURETISCHES MITTEL<br/>[EN] XANTHINE DERIVATIVES FOR USE AS DIURETICS<br/>[FR] DERIVES DE XANTHINE UTILISES COMME DIURETIQUES
  申请人：BOEHRINGER INGELHEIM KG

  公开号：WO1994011000A1

  公开（公告）日：1994-05-26

  (DE) Die vorliegende Erfindung betrifft die Verwendung von 8-(3-Oxocyclopentyl)-1,3-dipropyl-7H-purin-2,6-dion als Diuretikum.(EN) The invention concerns the use of 8-(3-oxocyclopentyl)-1,3-dipropyl-7H-purin-2,6-dione as a diuretic.(FR) L'invention concerne l'utilisation de 8-(3-oxocyclopentyl)-1,3-dipropyl-7H-purine-2,6-dione comme diurétique.

  本发明涉及使用8-（3-氧基环戊yl）-1,3-二丙基-7H-吡啶-2,6-酮作为利尿剂。