1-Phenyl-5-propan-2-ylidene-1,3-diazinane-2,4,6-trione | 207602-44-6

• 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: 1-Phenyl-5-propan-2-ylidene-1,3-diazinane-2,4,6-trione
• CAS: 207602-44-6
• 化学式: C₁₃H₁₂N₂O₃
• 分子量: 244.25
• InChiKey: LKMIIGFXDUERNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Phenyl-5-propan-2-ylidene-1,3-diazinane-2,4,6-trione 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、220.64 kPa 条件下， 反应 5.0h， 生成 5-isopropyl-1-phenylbarbituric acid
  参考文献：
  名称：

  Synthesis and antifungal activity of substituted 2,4,6-pyrimidinetrione carbaldehyde hydrazones

  摘要：

  Opportunistic fungal infections caused by the Candida spp. are the most common human fungal infections, often resulting in severe systemic infections-a significant cause of morbidity and mortality in at-risk populations. Azole antifungals remain the mainstay of antifungal treatment for candidiasis, however development of clinical resistance to azoles by Candida spp. limits the drugs' efficacy and highlights the need for discovery of novel therapeutics. Recently, it has been reported that simple hydrazone derivatives have the capability to potentiate antifungal activities in vitro. Similarly, pyrimidinetrione analogs have long been explored by medicinal chemists as potential therapeutics, with more recent focus being on the potential for pyrimidinetrione antimicrobial activity. In this work, we present the synthesis of a class of novel hydrazone-pyrimidinetrione analogs using novel synthetic procedures. In addition, structure-activity relationship studies focusing on fungal growth inhibition were also performed against two clinically significant fungal pathogens. A number of derivatives, including phenylhydrazones of 5-acylpyrimidinetrione exhibited potent growth inhibition at or below 10 mu M with minimal mammalian cell toxicity. In addition, in vitro studies aimed at defining the mechanism of action of the most active analogs provide preliminary evidence that these compound decrease energy production and fungal cell respiration, making this class of analogs promising novel therapies, as they target pathways not targeted by currently available antifungals. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.010
• 作为产物：
  描述：

  苯基脲 在 sodium ethanolate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 0.5h， 生成 1-Phenyl-5-propan-2-ylidene-1,3-diazinane-2,4,6-trione
  参考文献：
  名称：

  Synthesis and antifungal activity of substituted 2,4,6-pyrimidinetrione carbaldehyde hydrazones

  摘要：

  Opportunistic fungal infections caused by the Candida spp. are the most common human fungal infections, often resulting in severe systemic infections-a significant cause of morbidity and mortality in at-risk populations. Azole antifungals remain the mainstay of antifungal treatment for candidiasis, however development of clinical resistance to azoles by Candida spp. limits the drugs' efficacy and highlights the need for discovery of novel therapeutics. Recently, it has been reported that simple hydrazone derivatives have the capability to potentiate antifungal activities in vitro. Similarly, pyrimidinetrione analogs have long been explored by medicinal chemists as potential therapeutics, with more recent focus being on the potential for pyrimidinetrione antimicrobial activity. In this work, we present the synthesis of a class of novel hydrazone-pyrimidinetrione analogs using novel synthetic procedures. In addition, structure-activity relationship studies focusing on fungal growth inhibition were also performed against two clinically significant fungal pathogens. A number of derivatives, including phenylhydrazones of 5-acylpyrimidinetrione exhibited potent growth inhibition at or below 10 mu M with minimal mammalian cell toxicity. In addition, in vitro studies aimed at defining the mechanism of action of the most active analogs provide preliminary evidence that these compound decrease energy production and fungal cell respiration, making this class of analogs promising novel therapies, as they target pathways not targeted by currently available antifungals. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.010

文献信息

• Medicinal drug with activity against gram positive bacteria, mycobacteria and fungi
  申请人：Levina Elizabeth

  公开号：US10265318B2

  公开（公告）日：2019-04-23

  A medicinal drug is provided with activity against gram positive bacteria, mycobacteria and fungi characterized in that it is a compound of the class of pyrimidine derivatives of salicylic aldehyde and perhydropyrimidine-2,4,6-triones selected from a group consisting of tautomeric forms, salt forms, and a cyclic form of pyrylium salts, and with the general formula: where X1, X3 are selected from the group containing: H, halogen; NO2; X2, X4 are selected from the group containing: H, halogen; Z is selected from the group containing: O, NNH2, NOH, perhydropyrimidine-5-ylidene-2,4.6-trione, perhydropyrimidine-5-ylidene-2,4.6-trione, substituted at the nitrogen atom with alkyl, aryl or aralkyl group; Y is selected from the group containing: H, Na, Li, K. Further, methods for treating infections, tonsillitis, pneumonia, or wound infections caused by Gram-positive bacteria, mycobacteria and fungi are provided using a therapeutically effective amount of the compound.

  提供了一种对革兰氏阳性菌、分枝杆菌和真菌具有活性的药物，其特征在于它是一种水杨醛和过氢嘧啶-2,4,6-三酮的嘧啶衍生物类化合物，该化合物从同分异构体、盐类和环状嘧啶盐组成的组中选出，通式为 其中 X1、X3 选自以下组别H、卤素 X2、X4 选自包含以下物质的组H、卤素； Z 选自包含以下物质的组O、NNH2、NOH、全氢嘧啶-5-亚基-2,4.6-三酮、全氢嘧啶-5-亚基-2,4.6-三酮，在氮原子上被烷基、芳基或芳烷基取代； Y 选自以下组别H、Na、Li、K。 此外，还提供了使用治疗有效量的化合物治疗革兰氏阳性菌、分枝杆菌和真菌引起的感染、扁桃体炎、肺炎或伤口感染的方法。
• Medicinal Drug with Activity against Gram Positive Bacteria, Mycobacteria and Fungi
  申请人：Levina Elizabeth

  公开号：US20170035758A1

  公开（公告）日：2017-02-09

  A medicinal drug is provided with activity against gram positive bacteria, mycobacteria and fungi characterized in that it is a compound of the class of pyrimidine derivatives of salicylic aldehyde and perhydropyrimidine-2,4,6-triones selected from a group consisting of tautomeric forms, salt forms, and a cyclic form of pyrylium salts, and with the general formula: where X1, X3 are selected from the group containing: H, halogen; NO 2 ; X2, X4 are selected from the group containing: H, halogen; Z is selected from the group containing: O, NNH 2 , NOH, perhydropyrimidine-5-ylidene-2,4.6-trione, perhydropyrimidine-5-ylidene-2,4.6-trione, substituted at the nitrogen atom with alkyl, aryl or aralkyl group; Y is selected from the group containing: H, Na, Li, K. Further, methods for treating infections, tonsillitis, pneumonia, or wound infections caused by Gram-positive bacteria, mycobacteria and fungi are provided using a therapeutically effective amount of the compound.