1-oxa-4-azacyclohexadecan-16-one | 175859-47-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 1-oxa-4-azacyclohexadecan-16-one
• 英文别名: 13-aza-1,15-pentadecanolide
• CAS: 175859-47-9
• 化学式: C₁₄H₂₇NO₂
• 分子量: 241.374
• InChiKey: QBAHAZPZXJXBOU-UHFFFAOYSA-N

物化性质

• 沸点：
  399.0±25.0 °C(Predicted)
• 密度：
  0.902±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-oxa-4-azacyclohexadecan-16-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 tert-butyloxycarbonyl-2-methylene-12a-azapentadecanelactone
  参考文献：
  名称：

  Novel macrocyclic molecules based on 12a-N substituted 16-membered azalides and azalactams as potential antifungal agents

  摘要：

  Novel macrocyclic molecules comprising sulfonyl and acyl moiety at the position N-12a of 16-membered azalides (6a-n) and azalactams (10a-r) scaffold were synthesized from cyclododecanone 1 as starting material via 5 steps and 4 steps, respectively. The antifungal activity of these compounds against Sclerotinia sclerotiorum, Pyricularia oryzae, Botlytis cinerea, Rhizoctonia solani and Phytophthora capsici were evaluated and found that compounds possessing alpha-exomethylene (6c, 6d, 6e and 6g) showed antifungal activity comparable to commercial fungicide Chlorothalonil against P. oryzae and compounds possessing p-chlorobenzoyl exhibited enhanced antifungal activity than those with other substituents against S. sclerotiorum, P. oryzae, and B. cinerea. These findings suggested that the alpha-exomethylene and p-chlorobenzoyl may be two potential pharmacological active groups with antifungal activities. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.032
• 作为产物：
  描述：

  13-aza-1,15-cyclopentadecanolide fluoroborate 在 水 、 sodium carbonate 作用下， 生成 1-oxa-4-azacyclohexadecan-16-one
  参考文献：
  名称：

  Novel macrocyclic molecules based on 12a-N substituted 16-membered azalides and azalactams as potential antifungal agents

  摘要：

  Novel macrocyclic molecules comprising sulfonyl and acyl moiety at the position N-12a of 16-membered azalides (6a-n) and azalactams (10a-r) scaffold were synthesized from cyclododecanone 1 as starting material via 5 steps and 4 steps, respectively. The antifungal activity of these compounds against Sclerotinia sclerotiorum, Pyricularia oryzae, Botlytis cinerea, Rhizoctonia solani and Phytophthora capsici were evaluated and found that compounds possessing alpha-exomethylene (6c, 6d, 6e and 6g) showed antifungal activity comparable to commercial fungicide Chlorothalonil against P. oryzae and compounds possessing p-chlorobenzoyl exhibited enhanced antifungal activity than those with other substituents against S. sclerotiorum, P. oryzae, and B. cinerea. These findings suggested that the alpha-exomethylene and p-chlorobenzoyl may be two potential pharmacological active groups with antifungal activities. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.032

文献信息

• Synthesis, bioactivity and 3D-QSAR of azamacrolide compounds with a carbamate or urea moiety as potential fungicides and inhibitors of quorum sensing
  作者：Lei Ning、Simin Wang、Lin Du、Bingyi Guo、Jianjun Zhang、Huizhe Lu、Yanhong Dong

  DOI：10.1039/d0nj05727d

  日期：——

  sclerotiorum. Additionally, D16-19 could be used as a potential broad-spectrum fungicide while D16-4 exhibited a fungicidal activity (EC50 = 1.87 mg L−1) similar to that of carbendazim (EC50 = 1.34 mg L−1) against S. sclerotiorum. The three-dimensional Quantitative Structure–Activity Relationship (3D-QSAR) models were also established based on the experimental results and they would provide valuable

  合成了一系列含有氨基甲酸酯或脲部分的氮杂内酰胺，并评估了其对几种农业重要病原体的杀真菌活性。另外，还研究了它们在根癌土壤杆菌中抑制群体感应的能力。结果表明，大多数衍生物对被测真菌，特别是对核盘菌具有中等至较高的杀真菌活性。此外，D16-19可用作潜在的广谱杀菌剂，而D16-4的杀真菌活性（EC 50 = 1.87 mg L -1）类似于多菌灵（EC 50 = 1.34 mg L -1）。）对抗葡萄球菌。基于实验结果，建立了三维定量构效关系（3D-QSAR）模型，这些模型将为进一步优化提供有价值的信息。此外，D16-17不仅显示出更好的抗核盘菌的杀真菌活性，而且还具有最高的群体感应抑制能力。这些发现表明，某些氮杂大环内酯化合物具有开发新型杀菌剂或群体感应抑制剂的潜力。
• Synthesis and Biological Evaluation of Azamacrolide Comprising the Triazole Moiety as Quorum Sensing Inhibitors
  作者：Bin Zhang、Bingyi Guo、Yunlong Bai、Huizhe Lu、Yanhong Dong

  DOI：10.3390/molecules23051086

  日期：——

  Novel azamacrolides comprising the triazole moiety were synthesized and evaluated for their quorum sensing inhibitor activities on the Agrobacterium tumefaciens. It was found that the inhibition rate of compound Z12-3 at 200 mg/L (0.45 mM) can reach 67%. The potential binding modes between these molecules and the TraR QS receptor was performed by molecular docking. The results showed that the two nitrogen

  合成了包含三唑部分的新型氮杂大环内酯，并评估了它们对根癌农杆菌的群体感应抑制剂活性。发现化合物Z12-3在200mg/L(0.45mM)时的抑制率可达67%。这些分子与 TraR QS 受体之间的潜在结合模式是通过分子对接进行的。结果表明，Z12-3三唑环上的两个氮原子与GLN-2形成氢键，酰胺中的羰基(C=O)与水形成氢键。值得注意的是，大环内酯上的羰基与 DNA 中的 G-106 碱基形成氢键。这些氮杂大环内酯可以通过氢键键合 TraR QS 受体中的关键氨基酸残基或 DNA 碱基来阻断群体感应表达。
• Synthesis of a Mexican bean beetle azamacrolide allomone via a novel lactam to lactone ring expansion
  作者：Gordon W. Gribble、Richard A. Silva

  DOI：10.1016/0040-4039(96)00234-1

  日期：1996.3

  The Mixican bean beetle (Epilachna varivestis) defensive secretion azamacrolide 1 has been synthesized via the novel ring expansion of N-hydroxyethyl lactam 12, which was prepared in seven steps from cyclooctanone (6).

  通过N-羟乙基内酰胺12的新型扩环合成了Mixican豆甲虫（Epilachna varivestis）防御性分泌氮杂crocrolide 1，它是由环辛酮（7）分七个步骤制备的。
• 一种改进的氮杂大环内酯化合物及其制备方 法和用途
  申请人：中国农业大学

  公开号：CN105732535B

  公开（公告）日：2019-03-19

  本发明属于新农药创制有机合成领域，具体涉及一种改进的的氮杂大环内酯化合物及其制备方法，该化合物及其可药用盐含有氨基脲、噁二唑、硫脲衍生物中的一种。该制备方法至少包括以下步骤：a)将环十二酮与叠氮乙醇进行Schmidt反应后，经NaOH水解得到13‑氮杂‑1,15‑十五内酯，反应式如下：上述化合物均具有较好的杀菌和杀虫活性，且其活性优于母体。这为以后的新农药创制提供了有力的参考，具有作为新农药继续研发的潜力。
• 农药用含氨基甲酸酯或脲类结构的氮杂大环 内酯化合物及其制备方法和用途
  申请人：中国农业大学

  公开号：CN108484521B

  公开（公告）日：2020-10-23

  本发明的目的是提供一种农药用含氨基甲酸酯或脲类结构的氮杂大环内酯化合物和制备方法及其作为杀菌剂和群体感应调节剂的应用。该化合物的结构如通式(I)所示：本发明中，含氨基甲酸酯基团的氮杂大环内酯化合物和含脲类结构的氮杂大环内酯化合物均具有较好的杀菌和群体感应活性，且其活性优于母体，可用于制备新型农药。