acide heptyl-5 barbiturique | 14077-84-0

• 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: acide heptyl-5 barbiturique
• 英文别名: 5-Heptylpyrimidine-2,4,6(1h,3h,5h)-trione；5-heptyl-1,3-diazinane-2,4,6-trione
• CAS: 14077-84-0
• 化学式: C₁₁H₁₈N₂O₃
• mdl: MFCD02943833
• 分子量: 226.276
• InChiKey: KBFOQFLBOGLELW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  75.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  acide heptyl-5 barbiturique 在 chromium(VI) oxide 、 溶剂黄146 作用下， 以15%的产率得到acide hydroxy-5 heptyl-5 barbiturique
  参考文献：
  名称：

  Influence de la lipophilie sur l'oxydation biologique d'une chaîne méthyl-3 butyle en série barbiturique

  摘要：

  DOI：

  10.1016/0223-5234(88)90139-0
• 作为产物：
  描述：

  壬醛 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 5.5h， 生成 acide heptyl-5 barbiturique
  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

• Reductive C-alkylation of barbituric acid derivatives with carbonyl compounds in the presence of platinum and palladium catalysts
  作者：Branko S Jursic、Donna M Neumann

  DOI：10.1016/s0040-4039(01)00621-9

  日期：2001.6

  Effective synthetic procedures for the preparation of mono- and di-C-alkylated barbituric acid derivatives through palladium and platinum catalytic hydrogenation of solutions of barbituric acids (unsubstituted, N-mono, and N,N′-disubstituted barbituric acids) and carbonyl compounds (aliphatic and aromatic aldehydes and ketones).

  有效的单-和二-制备合成程序Ç通过钯和巴比土酸溶液的铂催化氢化烷基化巴比土酸衍生物（未取代的，Ñ -单和Ñ，N'二取代的巴比土酸）和羰基化合物（脂族和芳族醛和酮）。
• LAFONT, OLIVIER;TALAB, AKRAM;MENAGER, SABINE;CAVE, CHRISTIAN;MIOCQUE, MAR+, EUR. J. MED. CHEM., 23,(1988) N, C. 427-432
  作者：LAFONT, OLIVIER、TALAB, AKRAM、MENAGER, SABINE、CAVE, CHRISTIAN、MIOCQUE, MAR+

  DOI：——

  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.
• Influence de la lipophilie sur l'oxydation biologique d'une chaîne méthyl-3 butyle en série barbiturique
  作者：O Lafont

  DOI：10.1016/0223-5234(88)90139-0

  日期：1988.10