DDD00175285 | 110449-11-1

• 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: DDD00175285
• 英文别名: 5-Cinnamylidene-1,3-dimethyl-1,3-diazinane-2,4,6-trione
• CAS: 110449-11-1
• 化学式: C₁₅H₁₄N₂O₃
• 分子量: 270.288
• InChiKey: LPVZBHMLVXKEEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  DDD00175285 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 1,3-dimethyl-5-(3-phenylpropyl)pyrimidine-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
• 作为产物：
  描述：

  1,3-二甲基巴比妥酸 、 肉桂醛 在 PVP-Ni nanoparticle 作用下， 以 乙二醇 为溶剂， 以84%的产率得到DDD00175285
  参考文献：
  名称：

  镍纳米颗粒催化芳香醛与巴比妥酸和 2-硫代巴比妥酸的 Knoevenagel 缩合

  摘要：

  已经报道了在聚乙烯吡咯烷酮 (PVP) 稳定的 Ni 纳米粒子存在于乙二醇中的情况下，芳香醛与巴比妥酸和 2-硫代巴比妥酸的 Knoevenagel 缩合的有效途径。在很短的反应时间内以高产率 (82-97%) 获得了一系列生物学上重要的亚芳基巴比妥酸盐。图文摘要描述了一种新型高效的 PVP 稳定的 Ni 纳米粒子催化合成亚芳基巴比妥酸盐和亚芳基 2-硫代巴比妥酸盐。

  DOI：

  10.1007/s10562-010-0376-2

文献信息

• Nickel Nanoparticles Catalyzed Knoevenagel Condensation of Aromatic Aldehydes with Barbituric Acids and 2-Thiobarbituric Acids
  作者：Jitender M. Khurana、Kanika Vij

  DOI：10.1007/s10562-010-0376-2

  日期：2010.8

  An efficient route for the Knoevenagel condensation of aromatic aldehydes with barbituric acids and 2-thiobarbituric acids in the presence of polyvinyl pyrrolidone (PVP) stabilized Ni nanoparticles in ethylene glycol has been reported. A range of biologically important arylidene barbiturates were obtained in high yields (82–97%) in a very short reaction time.Graphical AbstractA novel and highly efficient

  已经报道了在聚乙烯吡咯烷酮 (PVP) 稳定的 Ni 纳米粒子存在于乙二醇中的情况下，芳香醛与巴比妥酸和 2-硫代巴比妥酸的 Knoevenagel 缩合的有效途径。在很短的反应时间内以高产率 (82-97%) 获得了一系列生物学上重要的亚芳基巴比妥酸盐。图文摘要描述了一种新型高效的 PVP 稳定的 Ni 纳米粒子催化合成亚芳基巴比妥酸盐和亚芳基 2-硫代巴比妥酸盐。
• Asymmetric higher-order [10 + <i>n</i>] cycloadditions of palladium-containing 10π-cycloaddends
  作者：Ao Li、Yang Gao、Jian-Bin Lu、Zhi-Chao Chen、Wei Du、Ying-Chun Chen

  DOI：10.1039/d2sc02985e

  日期：——

  [10 + 2] cycloaddition reaction between diverse activated alkenes and a new type of π-allylpalladium complex-containing dipole-type 10π-cycloaddend, which was generated in situ from 2-methylene-1-indanols via a dehydrative insertion and deprotonation strategy under double activation of Pd(0) and phosphoric acid. A similar strategy was applied to an asymmetric higher-order [10 + 8] cycloaddition reaction

  我们发现了多种活化烯烃和一种新型含有偶极型 10π-环加成物的 π-烯丙基钯配合物之间的不对称高阶 [10 + 2] 环加成反应，该反应是由 2-亚甲基-1-茚满醇原位生成的Pd(0)和磷酸双重激活下的脱水插入和去质子化策略。通过分别使用七富烯衍生物或环烯酮作为受体，将类似的策略应用于不对称高阶[10 + 8]环加成反应或[10 + 4]环加成反应。通过采用新设计的手性亚磷酰胺配体，嵌入茚核的各种多环骨架通常以中等至优异的产率提供，并具有高水平的对映选择性。
• 10.3184/174751911x556765
  作者：Shaabani, Ahamd、Teimouri, Mohammad Bagher、Afgheh, Mohammad、Eskandari, Mehrdad

  DOI：10.3184/174751911x556765

  日期：——
• Synthesis and antifungal activity of substituted 2,4,6-pyrimidinetrione carbaldehyde hydrazones
  作者：Donna M. Neumann、Amy Cammarata、Gregory Backes、Glen E. Palmer、Branko S. Jursic

  DOI：10.1016/j.bmc.2013.12.010

  日期：2014.1

  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.