5-(uracil-1'-yl)pentanal | 1001671-17-5

• 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-(uracil-1'-yl)pentanal
• 英文别名: 5-(2,4-Dioxopyrimidin-1-yl)pentanal
• CAS: 1001671-17-5
• 化学式: C₉H₁₂N₂O₃
• 分子量: 196.206
• InChiKey: VMKBGZSNKXNQQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  5-(uracil-1'-yl)pentanal 在 4-二甲氨基吡啶 、 sodium sulfate 、 N,N'-二环己基碳二亚胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 43.0h， 生成 (3S,6S,7R)-3-(benzyloxymethyl)-7-(tertbutyldiphenylsilyloxymethyl)-4-N-(5''-(uracil-1'-yl)pentyl)-6-palmitoyloxy-1,4-diazepan-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of a diazepanone-based library of liposidomycins analogs as MraY inhibitors

  摘要：

  New inhibitors of the bacterial tranferase MraY are described. A scaffold strategy based on the diazepanone central core of liposidomycins, natural inhibitors of MraY has been developed. It involves the introduction of key structural fragments required for biological activity on enantiopure diazepanones by reductive amination, esterification and glycosylation. Biological evaluation of these compounds on MraY enzyme revealed interesting inhibitory activity for compounds displaying three fragments on the scaffold: a palmitoyl chain, an aminoribose part and an alkyluracil moiety. The inhibitors were also evaluated on MurG enzyme. The best compounds resulted in inhibition with IC50 values in the 100 mu M range for one or the other enzyme. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.006
• 作为产物：
  描述：

  1-(ω-hydroxy-n-amyl)uracil 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 以77%的产率得到5-(uracil-1'-yl)pentanal
  参考文献：
  名称：

  迈向新的 MraY 抑制剂：尿嘧啶和 5-氨基-5-脱氧核糖基支架的丝氨酸模板

  摘要：

  细菌移位酶 MraY 是开发新抗生素的一个很好的目标，因为它无处不在，并且对细菌生长至关重要。这项工作的目标是合成这种酶的天然抑制剂的简化类似物，以研究这些抑制剂的尿苷部分在生物活性方面的基本特征。因此，目标对映体纯 N-(尿嘧啶基戊基)-β-DO-(5-氨基-5-脱氧核糖基)-L-丝氨酸的结构保留了尿嘧啶和通过丝氨酰模板连接的 5-氨基-5-脱氧核糖部分。该化合物的合成策略依赖于通过丝氨酸衍生物的还原胺化顺序进行的 O-糖基化和 N-烷基化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  DOI：

  10.1002/ejoc.200700527

文献信息

• Synthetic studies towards diazepanone scaffolds
  作者：Olivier Monasson、Maryon Ginisty、Janez Mravljak、Gildas Bertho、Christine Gravier-Pelletier、Yves Le Merrer

  DOI：10.1016/j.tetasy.2009.09.022

  日期：2009.10

  The synthesis of new enantiopure polyfunctionalised diazepanone scaffolds is described. The key steps involve the opening of an azido-epoxide C4 building block derived from L-ascorbic or D-isoascorbic acid by a L-serine derivative followed by a lactonisation-lactamisation two-step sequence. (C) 2009 Elsevier Ltd. All rights reserved.
• Towards New MraY Inhibitors: A Serine Template for Uracil and 5-Amino-5-deoxyribosyl Scaffolding
  作者：Laurent Le Corre、Christine Gravier-Pelletier、Yves Le Merrer

  DOI：10.1002/ejoc.200700527

  日期：2007.11

  the targeted enantiomerically pure N-(uracilylpentyl)-β-D-O-(5-amino-5-deoxyribosyl)-L-serine retains uracil and 5-amino-5-deoxyribose parts linked by a serinyl template. The synthetic strategy towards this compound relies on sequential O-glycosylation and N-alkylation by reductive amination of a serine derivative. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  细菌移位酶 MraY 是开发新抗生素的一个很好的目标，因为它无处不在，并且对细菌生长至关重要。这项工作的目标是合成这种酶的天然抑制剂的简化类似物，以研究这些抑制剂的尿苷部分在生物活性方面的基本特征。因此，目标对映体纯 N-(尿嘧啶基戊基)-β-DO-(5-氨基-5-脱氧核糖基)-L-丝氨酸的结构保留了尿嘧啶和通过丝氨酰模板连接的 5-氨基-5-脱氧核糖部分。该化合物的合成策略依赖于通过丝氨酸衍生物的还原胺化顺序进行的 O-糖基化和 N-烷基化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Synthesis and biological evaluation of a diazepanone-based library of liposidomycins analogs as MraY inhibitors
  作者：Janez Mravljak、Olivier Monasson、Bayan Al-Dabbagh、Muriel Crouvoisier、Ahmed Bouhss、Christine Gravier-Pelletier、Yves Le Merrer

  DOI：10.1016/j.ejmech.2011.02.006

  日期：2011.5

  New inhibitors of the bacterial tranferase MraY are described. A scaffold strategy based on the diazepanone central core of liposidomycins, natural inhibitors of MraY has been developed. It involves the introduction of key structural fragments required for biological activity on enantiopure diazepanones by reductive amination, esterification and glycosylation. Biological evaluation of these compounds on MraY enzyme revealed interesting inhibitory activity for compounds displaying three fragments on the scaffold: a palmitoyl chain, an aminoribose part and an alkyluracil moiety. The inhibitors were also evaluated on MurG enzyme. The best compounds resulted in inhibition with IC50 values in the 100 mu M range for one or the other enzyme. (C) 2011 Elsevier Masson SAS. All rights reserved.