5-(2-Benzyloxy-benzyl)-pyrimidine-2,4,6-trione | 242473-64-9

• 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-(2-Benzyloxy-benzyl)-pyrimidine-2,4,6-trione
• 英文别名: 5-[[2-(Phenylmethoxy)phenyl]methyl]-2,4,6(1H,3H,5H)-pyrimidinetrione；5-[(2-phenylmethoxyphenyl)methyl]-1,3-diazinane-2,4,6-trione
• CAS: 242473-64-9
• 化学式: C₁₈H₁₆N₂O₄
• 分子量: 324.336
• InChiKey: OTOBSWXRTLRDRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-苄氧基苯甲醛 在 sodium tetrahydroborate 、 水 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 5-(2-Benzyloxy-benzyl)-pyrimidine-2,4,6-trione
  参考文献：
  名称：

  Uridine phosphorylase inhibitors: Chemical modification of benzyloxybenzyl-barbituric acid and its effects on UrdPase inhibition

  摘要：

  5-(o-Benzyloxy)benzylbarbituric acid (6) and 5-(p-benzyloxy)benzylbarbituric acid (7) were prepared and their inhibitory activities compared to 5-(m-benzyloxy)-benzylbarbituric acid (BBB) a known, potent inhibitor of uridine phosphorylase (UrdPase). Compounds 6 and 7 were 18-fold and 51-fold less active, respectively, than BBB in inhibiting UrdPase. These data provide solid evidence that the 5-benzylbarbituric acids possessing meta substituents are the most active inhibitors. In addition, 2-thioBBB (11) was synthesized and it was shown to be as active an inhibitor as BBB. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00238-3

文献信息

• [EN] PYRIMIDINE DERIVATIVES FOR USE AS ANTIBIOTICS<br/>[FR] DÉRIVÉS DE PYRIMIDINE À UTILISER EN TANT QU'ANTIBIOTIQUES
  申请人：UNIV ASTON

  公开号：WO2010136804A1

  公开（公告）日：2010-12-02

  The invention provides a compound of formula (i): wherein R1 and R2 are independently selected from hydrogen, methyl, ethyl, propyl and butyl; R3 is selected from substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted 1-naphthyl, substituted 2-naphthyl, and substituted phenyl, and X1 and X3 are independently selected from O or S, and X2 is O; and L is selected from C1 to C3 alkyl, C1 to C3 alkoxyl, C2 or C3 alkenyl, and C2 or C3 alkynyl; and the bond connecting L to the ring is a single or a double bond; wherein when the bond connecting L to the pyrimidine ring is a double bond, the substituted phenyl is not a monosubstituted 2- or 4- halobenzene; and wherein the substituted phenyl is not a toluene, anisole, phenol, dimethylaniline, guaiacol, or benzyl phenyl ether moiety; or a pharmaceutically, or veterinarily, acceptable derivative thereof. The use of such compounds as medicaments, in particular as antibiotics, specifically antibiotics for the inhibition of bacterial DHODase is also described, as are compositions (pharmaceutical and anti-infective) containing the compositions, articles or surfaces coated impregnated with the anti- infective compositions. Finally, the invention provides methods for the treatment of a disease and methods for preventing bacterial transmission including the compounds of formula 1.

  这项发明提供了一个式（i）的化合物：其中R1和R2分别选自氢、甲基、乙基、丙基和丁基；R3选自取代或未取代的蒽基、取代或未取代的芘基、取代或未取代的咔唑基、取代或未取代的咪唑基、取代或未取代的菲基、取代或未取代的芴基、取代或未取代的1-萘基、取代的2-萘基和取代的苯基，X1和X3分别选自O或S，X2为O；L选自C1到C3烷基、C1到C3烷氧基、C2或C3烯基和C2或C3炔基；连接L到环的键为单键或双键；当连接L到嘧啶环的键为双键时，取代的苯基不是单取代的2-或4-卤苯；取代的苯基不是甲苯、甲酚、二甲基苯胺、愈创木酚或苄基苯醚基团；或其药学或兽医学上可接受的衍生物。还描述了这些化合物作为药物的用途，特别是作为抗生素，特别是用于抑制细菌DHODase的抗生素，以及含有这些化合物的组合物（药用和抗感染），涂有抗感染组合物的物品或表面。最后，该发明提供了一种治疗疾病的方法和预防细菌传播的方法，包括式1的化合物。
• UPS AS MODIFIERS OF THE BETA CATENIN PATHWAY AND METHODS OF USE
  申请人：Exelixis, Inc.

  公开号：EP1651674B1

  公开（公告）日：2010-09-29
• [EN] COMPOSITIONS, METHODS AND KITS RELATING TO URIDINE PHOSPHORYLASE GENE MUTATIONS<br/>[FR] COMPOSITIONS, METHODES ET KITS CONCERNANT DES MUTATIONS DU GENE PAR L'URIDINE PHOSPHORYLASE
  申请人：UNIV YALE

  公开号：WO2001060985A2

  公开（公告）日：2001-08-23

  The present invention relates to human uridine phosphorylase nucleic acids and proteins encoded thereby. More specifically, the invention discloses that uridine phosphorylase in certain tumor tissues is resistant to inhibition by uridine phosphorylase inhibitor (UPI). The invention further relates to identification of mutations associated with uridine phosphorylase resistance to UPIs. These mutations include mutations located in exon 1 and exon 6. More specifically, the mutations include, but are not limited to, a change from a C to T at nucleotide 40, a C to T at nucleotide 135, a C to G at nucleotide 178, an A to C at nucleotide 182, a C to T at nucleotide 186, a G to A at nucleotide 713, and a G to A at nucleotide 752. The invention also relates to methods and kits relating to the nucleic and amino encoding UPase resistant to UPIs and uses therefor.
• Uridine phosphorylase inhibitors: Chemical modification of benzyloxybenzyl-barbituric acid and its effects on UrdPase inhibition
  作者：David J. Guerin、Daniel Mazeas、Manoj S. Musale、Fardos N.M. Naguib、Omar N. Al Safarjalani、Mahmoud H. el Kouni、Raymond P. Panzica

  DOI：10.1016/s0960-894x(99)00238-3

  日期：1999.6

  5-(o-Benzyloxy)benzylbarbituric acid (6) and 5-(p-benzyloxy)benzylbarbituric acid (7) were prepared and their inhibitory activities compared to 5-(m-benzyloxy)-benzylbarbituric acid (BBB) a known, potent inhibitor of uridine phosphorylase (UrdPase). Compounds 6 and 7 were 18-fold and 51-fold less active, respectively, than BBB in inhibiting UrdPase. These data provide solid evidence that the 5-benzylbarbituric acids possessing meta substituents are the most active inhibitors. In addition, 2-thioBBB (11) was synthesized and it was shown to be as active an inhibitor as BBB. (C) 1999 Elsevier Science Ltd. All rights reserved.