3-(1-n-butyl-1H-tetrazol-5-yl)dihydrofuran-2(3H)-one | 1393720-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-(1-n-butyl-1H-tetrazol-5-yl)dihydrofuran-2(3H)-one
• 英文别名: 3-(1-Butyltetrazol-5-yl)oxolan-2-one
• CAS: 1393720-68-7
• 化学式: C₉H₁₄N₄O₂
• 分子量: 210.236
• InChiKey: DDLIQJLJCNWEBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  69.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氧代四氢呋喃-3-羧酸 在 4-二甲氨基吡啶 、 sodium azide 、 三氟甲磺酸酐 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 34.0h， 生成 3-(1-n-butyl-1H-tetrazol-5-yl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of new N-acyl-homoserine-lactone analogues, based on triazole and tetrazole scaffolds, acting as LuxR-dependent quorum sensing modulators

  摘要：

  New analogues of N-acyl-homoserine-lactone (AHL), in which the amide was replaced by a triazole or tetrazole ring, were prepared and tested for their activity as LuxR-dependent QS modulators. Several compounds showed a level of antagonistic or agonistic activity, notably some 1,4-triazolic and 1,5-tetrazolic derivatives, whereas the 2,5-tetrazolic compounds were inactive. In 1,5-tetrazoles, substituted with butyrolactone and an alkyl chain, the activity was reversed, depending on the connection between the lactone and the tetrazole. The C-N connected compounds were agonists whereas the C-C connected ones were antagonists. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.007

文献信息

• Synthesis and biological evaluation of new N-acyl-homoserine-lactone analogues, based on triazole and tetrazole scaffolds, acting as LuxR-dependent quorum sensing modulators
  作者：Mohamad Sabbah、Fanny Fontaine、Lucie Grand、Mohamed Boukraa、Mohamed L. Efrit、Alain Doutheau、Laurent Soulère、Yves Queneau

  DOI：10.1016/j.bmc.2012.06.007

  日期：2012.8

  New analogues of N-acyl-homoserine-lactone (AHL), in which the amide was replaced by a triazole or tetrazole ring, were prepared and tested for their activity as LuxR-dependent QS modulators. Several compounds showed a level of antagonistic or agonistic activity, notably some 1,4-triazolic and 1,5-tetrazolic derivatives, whereas the 2,5-tetrazolic compounds were inactive. In 1,5-tetrazoles, substituted with butyrolactone and an alkyl chain, the activity was reversed, depending on the connection between the lactone and the tetrazole. The C-N connected compounds were agonists whereas the C-C connected ones were antagonists. (C) 2012 Elsevier Ltd. All rights reserved.