5-[[3-(苯基甲氧基)苯基]甲基]-1,3-二嗪农-2,4,6-三酮 | 138660-08-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-[[3-(苯基甲氧基)苯基]甲基]-1,3-二嗪农-2,4,6-三酮
• 中文别名: 2-氨基丙基(9Z,12Z)-十八碳-9,12-二烯酸酯
• 英文名称: 5-(m-benzyloxy)benzylbarbituric acid
• 英文别名: 5-Benzyloxybenzylbarbituric acid；5-[(3-phenylmethoxyphenyl)methyl]-1,3-diazinane-2,4,6-trione
• CAS: 138660-08-9
• 化学式: C₁₈H₁₆N₂O₄
• 分子量: 324.336
• InChiKey: LHGZUAAZPCYFIW-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

• 作为反应物：
  描述：

  5-[[3-(苯基甲氧基)苯基]甲基]-1,3-二嗪农-2,4,6-三酮 在 三氯化铝 、 六甲基二硅氮烷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 48.0h， 生成 1-<(2-acetoxyethoxy)methyl>-5-(m-benzyloxy)benzylbarbituric acid
  参考文献：
  名称：

  Tzeng, Cherng-Chyi; Panzica, Raymond P.; Naguib, Fardos N.M., Journal of Heterocyclic Chemistry, 1993, vol. 30, # 5, p. 1399 - 1404

  摘要：

  DOI：
• 作为产物：
  描述：

  3-苄氧基苯甲醛 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 5-[[3-(苯基甲氧基)苯基]甲基]-1,3-二嗪农-2,4,6-三酮
  参考文献：
  名称：

  Tzeng, Cherng-Chyi; Panzica, Raymond P.; Naguib, Fardos N.M., Journal of Heterocyclic Chemistry, 1993, vol. 30, # 5, p. 1399 - 1404

  摘要：

  DOI：

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。
• Compositions and methods for treatment of mitochondrial diseases
  申请人：——

  公开号：US20020049182A1

  公开（公告）日：2002-04-25

  Compounds, compositions, and methods are provided for treatment of disorders related to mitochondrial dysfunction. The methods comprise administering to a mammal a composition containing pyrimidine nucleotide precursors in amounts sufficient to treat symptoms resulting from mitochondrial respiratory chain deficiencies.

  本发明提供了用于治疗与线粒体功能障碍有关的疾病的化合物、组合物和方法。该方法包括向哺乳动物投与含有嘧啶核苷酸前体的组合物，其量足以治疗因线粒体呼吸链缺陷而导致的症状。
• Compositions and the use thereof the treatment of mitochondrial diseases
  申请人：32 Mott Street Acquisitions I, LLC d/b/a Wellstat Vaccines

  公开号：EP2295063A2

  公开（公告）日：2011-03-16

  There is provided a method for treating or preventing pathophysiological consequences of mitochondrial respiratory chain dysfunction in a mammal comprising administering to said mammal in need of such treatment or prevention an effective amount of a pyrimidine nucleotide. There is also provided a method for reducing side effects of cytotoxic cancer chemotherapy agents by administering a pyrimidine nucleotide precursor, where said cytotoxic chemotherapy agent is not a pyrimidine nucleoside analog.

  提供了一种治疗或预防哺乳动物线粒体呼吸链功能障碍的病理生理后果的方法，该方法包括向需要这种治疗或预防的哺乳动物施用有效量的嘧啶核苷酸。还提供了一种通过施用嘧啶核苷酸前体减少细胞毒性癌症化疗剂副作用的方法，其中所述细胞毒性化疗剂不是嘧啶核苷类似物。
• Combating side-effects
  申请人：——

  公开号：US20040138157A1

  公开（公告）日：2004-07-15

  The invention relates to the use of active ingredients, which increase the concentration of pyrimidine-based elements for nucleic acid biosynthesis in the body, in particular to the use of pyrimidine nucleosides and/or prodrugs produced therefrom, for reducing the side-effects of inhibitors of nucleic acid biosynthesis or their precursors, in particular by activating the biosynthesis of mitochondrial DNA (mtDNA). The invention also relates to the use of said active ingredients, in particular pyrimidine nucleosides and/or prodrugs for producing pharmaceutical preparations for reducing the aforementioned side-effects and to combinations or products for administering active ingredients of this type, in particular pyrimidine nucleosides and/or prodrugs produced therefrom, comprising inhibitors of nucleic acid biosynthesis or their precursors. The invention further relates to methods for treating the side-effects of inhibitors of nucleic acid biosynthesis or their precursors using the aforementioned active ingredients, in particular pyrimidine nucleosides and/or prodrugs produced therefrom, or the aforementioned combinations or products and to corresponding pharmaceutical preparations. Side-effects of HAART (Highly Active Anti-Retroviral Therapy) and side-effects of other anti-viral nucleoside analogous agents, which inhibit the mitochondrial &ggr;-polymerases, can in particular be prophylactically and/or therapeutically treated in this manner.

  本发明涉及增加体内核酸生物合成所需的嘧啶类元素浓度的活性成分的使用，特别是嘧啶核苷和/或由此产生的原药的使用，以减少核酸生物合成抑制剂或其前体的副作用，特别是通过激活线粒体DNA（mtDNA）的生物合成。本发明还涉及使用上述活性成分，特别是嘧啶核苷和/或原药生产减少上述副作用的药物制剂，并涉及施用这类活性成分，特别是嘧啶核苷和/或由其生产的原药的组合物或产品，包括核酸生物合成抑制剂或其前体。本发明还涉及使用上述活性成分，特别是嘧啶核苷和/或由此产生的原药，或上述组合或产品，治疗核酸生物合成抑制剂或其前体的副作用的方法，以及相应的药物制剂。HAART（高活性抗逆转录病毒疗法）的副作用和其他抗病毒核苷类药物的副作用，特别是抑制线粒体聚合酶的副作用，可以通过这种方式进行预防和/或治疗。
• Exploring new inhibitors of Plasmodium falciparum purine nucleoside phosphorylase
  作者：Huaqing Cui、Gian Filippo Ruda、Juana Carrero-Lérida、Luis M. Ruiz-Pérez、Ian H. Gilbert、Dolores González-Pacanowska

  DOI：10.1016/j.ejmech.2010.08.026

  日期：2010.11

  Plasmodium falciparum purine nucleoside phosphorylase (PfPNP) has a central role in purine salvage and inhibitors of the enzyme have been shown to have antiplasmodial activity. The enzyme preferentially uses inosine as substrate (K-m = 51 mu M, k(cat)/K-m = 7.4 x 10(4) M-1 s(-1)), but can also use uridine, albeit less efficiently (K-m = 85 mu M, k(cat)/K-m = 306 M-1 s(-1)). In an effort to identify new PfPNP inhibitors, two series of compounds were prepared. Series 1 was based on known human uridine phosphorylase inhibitors whilst series 2 was uracil equivalents of purine-based PNP transition state inhibitors. These two series of compounds were assayed for inhibition of both PfPNP activity and growth of P. falciparum. The transition state analogues were found to be moderate inhibitors of PfPNP (most potent compound, K-i = 6 mu M). (C) 2010 Elsevier Masson SAS. All rights reserved.