5-amino-1,3-bis-n-propyluracil | 51038-42-7

• 物质功能分类: 医药中间体 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-amino-1,3-bis-n-propyluracil
• 英文别名: 5-amino-1,3-dipropyl-2,4-(1H,3H)-pyrimidinedione；5-Amino-1,3-dipropylpyrimidine-2,4(1H,3H)-dione；5-amino-1,3-dipropylpyrimidine-2,4-dione
• CAS: 51038-42-7
• 化学式: C₁₀H₁₇N₃O₂
• 分子量: 211.264
• InChiKey: FQYGPYPJUIUQHP-UHFFFAOYSA-N

物化性质

• 沸点：
  308.3±45.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氯吡啶 、 5-amino-1,3-bis-n-propyluracil 在 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.17h， 以67%的产率得到1,3-bis-n-propyl-5-(pyridin-3-ylamino)uracil
  参考文献：
  名称：

  Synthesis of hybrid analogues of caffeine and eudistomin D and its affinity for adenosine receptors

  摘要：

  Four bis-N-n-propyl analogues (3-6) in the uracil ring of two hybrid molecules (1 and 2) of caffeine and eudistomin D, a beta-carboline alkaloid from a marine tunicate, were synthesized, and their affinity and selectivity for adenosine receptors A(1), A(2A), and A(3) were examined. All the compounds (3-6) showed better potency as adenosine receptor ligands than caffeine. Bis-N-n-propylation (3 and 4, respectively) of the uracil ring in 1 and 2 resulted in higher affinity for A(1) and A(2A) adenosine receptors. Furthermore, it was found that a compound (5) possessing a n-propyloxy group at C-7 in compound 3 with a nitrogen at the beta-position of the pyridine ring (beta-N type) enhanced remarkably affinity for adenosine receptor A3 subtype, while n-propyloxy substitution (compound 6) at C-5 in compound 4 with a nitrogen at the delta-position of the pyridine ring (delta-N type) reduced affinity for all the adenosine receptor, A(1), A(2A), and A(3). Among all the compounds (1-6) examined, compound 5 showed the most potent affinity for adenosine receptor A(3) subtype (K-i value, 0.00382 mu M). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.036
• 作为产物：
  描述：

  5-nitro-1,3-bis-n-propyluracil 在 铁粉 、 溶剂黄146 作用下， 反应 4.0h， 以86%的产率得到5-amino-1,3-bis-n-propyluracil
  参考文献：
  名称：

  Synthesis of hybrid analogues of caffeine and eudistomin D and its affinity for adenosine receptors

  摘要：

  Four bis-N-n-propyl analogues (3-6) in the uracil ring of two hybrid molecules (1 and 2) of caffeine and eudistomin D, a beta-carboline alkaloid from a marine tunicate, were synthesized, and their affinity and selectivity for adenosine receptors A(1), A(2A), and A(3) were examined. All the compounds (3-6) showed better potency as adenosine receptor ligands than caffeine. Bis-N-n-propylation (3 and 4, respectively) of the uracil ring in 1 and 2 resulted in higher affinity for A(1) and A(2A) adenosine receptors. Furthermore, it was found that a compound (5) possessing a n-propyloxy group at C-7 in compound 3 with a nitrogen at the beta-position of the pyridine ring (beta-N type) enhanced remarkably affinity for adenosine receptor A3 subtype, while n-propyloxy substitution (compound 6) at C-5 in compound 4 with a nitrogen at the delta-position of the pyridine ring (delta-N type) reduced affinity for all the adenosine receptor, A(1), A(2A), and A(3). Among all the compounds (1-6) examined, compound 5 showed the most potent affinity for adenosine receptor A(3) subtype (K-i value, 0.00382 mu M). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.036

文献信息

• Substituted 8-phenylxanthines
  申请人：Warner-Lambert Company

  公开号：US04452788A1

  公开（公告）日：1984-06-05

  Substituted 8-phenylxanthines and their use as bronchodilators is described. Methods for their preparation and use as well as pharmaceutical compositions containing them are also described.

  本文描述了8-苯基黄嘌呤及其作为支气管扩张剂的用途。同时还描述了它们的制备和使用方法，以及含有它们的制药组合物。
• STABILISATORZUSAMMENSETZUNGEN FÜR HALOGENHALTIGE POLYMERE MIT VERBESSERTER ANFANGSFARBE UND VERBESSERTER FARBHALTUNG
  申请人：Baerlocher GmbH

  公开号：EP1996649A1

  公开（公告）日：2008-12-03
• STABILIZER COMPOSITIONS FOR HALOGENATED POLYMERS WITH IMPROVED INITIAL COLOR AND IMPROVED COLOR MAINTENANCE
  申请人：Fokken Stefan

  公开号：US20090048374A1

  公开（公告）日：2009-02-19

  A stabilizer composition for halogenated polymers includes at least one compound from group A) and at least one compound from group B), group A) being composed of semicarbazides, carbazides, carbazones, and carbodiazones, and their salts, and group B) of guanidines and melamines, superacids and salts of superacids, epoxy and glycidyl compounds, 1,3-dicarbonyl compounds, polyols, sterically hindered amines, hydrotalcites, zeolites, and alkali metal aluminocarbonates, hydrocalumites, metal hydroxides, metal oxides, metal hydrogen carbonates, and metal carbonates, metal soaps, organotin compounds, organic phosphite esters, amino alcohols and hydroxyl-containing isocyanurates, α,β-unsaturated β-aminocarbonyl compounds, aminouracil compounds and aminothiouracil compounds, and compounds having at least one mercapto-functional, sp 2 -hybridized C atom. Polymers stabilized in accordance with the invention are notable in particular for improved initial color and also for improved color maintenance.
• US4452788A
  申请人：——

  公开号：US4452788A

  公开（公告）日：1984-06-05
• [DE] STABILISATORZUSAMMENSETZUNGEN FÜR HALOGENHALTIGE POLYMERE MIT VERBESSERTER ANFANGSFARBE UND VERBESSERTER FARBHALTUNG<br/>[EN] STABILIZER COMPOSITIONS FOR HALOGENATED POLYMERS WITH IMPROVED INITIAL COLOR AND IMPROVED COLOR MAINTENANCE<br/>[FR] COMPOSITIONS STABILISANTES POUR POLYMERES CONTENANT DES HALOGENES PRESENTANT UNE COULEUR DE DEPART AMELIOREE ET UNE MEILLEURE TENUE DES COULEURS
  申请人：BAERLOCHER GMBH

  公开号：WO2007104379A1

  公开（公告）日：2007-09-20

  [EN] The present invention relates to a stabilizer composition for halogenated polymers, comprising at least one compound from group A) and at least one compound from group B), group A) consisting of semicarbazides, carbazides, carbazones and carbodiazones and salts thereof, and group B) of guanidines and melamines, superacids and salts of the superacids, epoxy and glycidyl compounds, 1,3-dicarbonyl compounds, polyols, sterically hindered amines, hydrotalcites, zeolites and alkali metal aluminocarbonates, hydrocalumites, metal hydroxides, metal oxides, metal hydrogencarbonates and metal carbonates, metal soaps, organotin compounds, organic phosphite esters, amino alcohols and hydroxyl-containing isocyanurates, a,b-unsaturated b-aminocarbonyl compounds, aminouracil compounds and aminothiouracil compounds and compounds having at least one mercapto-functional sp²-hybridized carbon atom. Polymers stabilized in accordance with the invention feature especially improved initial color and improved color maintenance.
  [FR] La présente invention concerne une composition stabilisante pour polymères contenant des halogènes, comprenant au moins un composé du groupe A) et au moins un composé du groupe B), le groupe A) comprenant les semi-carbazides, les carbazides, les carbazones et les carbodiazones et leurs sels et le groupe B) comprenant les guanidines et mélamines, les superacides et les sels des superacides, les composés d'époxy et de glycidyle, les composés de 1,3-dicarbonyle, les polyols, les amines encombrées stériquement, les hydrotalcites, les zéolites et les carbonates d'alcalis, les hydrocalumites, les hydroxydes métalliques, les oxydes métalliques, les hydrogénocarbonates métalliques et les carbonates métalliques, les carboxylates métalliques, les composés d'organoétain, les esters de phosphite organiques, les aminoalcools et les isocyanurates contenant des groupements hydroxyle, les composés ß-aminocarbonyle a,ß-insaturés, les composés aminouracile et les composés aminothiouracile et les composés ayant au moins un atome de carbone à hybridation sp² et fonction mercapto. Selon l'invention, les polymères stabilisés présentent notamment une couleur de départ améliorée et une meilleure tenue des couleurs.
  [DE] Die vorliegende Erfindung betrifft eine Stabilisatorzusammensetzung für halogenhaltige Polymere umfassend mindestens eine Verbindung aus der Gruppe A) und mindestens eine Verbindung aus der Gruppe B), wobei die Gruppe A) aus Semicarbaziden, Carbaziden, Carbazonen und Carbodiazonen und deren Salzen und die Gruppe B) aus Guanidinen und Melaminen, Supersäuren und Salzen der Supersäuren, Epoxy- und Glycidylverbingungen, 1,3-Dicarbonylverbindungen, Polyolen, sterisch gehinderten Aminen, Hydrotalciten, Zeolithen und Alkalialumocarbonaten, Hydrocalumiten, Metallhydroxiden, Metalloxiden, Metallhydrogencarbonaten und Metallcarbonaten, Metallseifen, Organozinnverbindungen, organischen Phosphitestern, Aminoalkoholen und hydroxylgruppenhaltigen Isocyanuraten, a,ß-ungesättigten ß-Aminocarbonylverbindungen, Aminouracilverbindungen und Aminothiouracilverbindungen und Verbindungen mit mindestens einem mercaptofunktionellen, sp²-hybridisierten C-Atom besteht. Erfindungsgemäß stabilisierte Polymere zeichnen sich insbesondere durch eine verbesserte Anfangsfarbe sowie eine verbesserte Farbhaltung aus.