α-(n-Butylcarbamoyl)-γ-butyrolacton | 52217-14-8

• 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: α-(n-Butylcarbamoyl)-γ-butyrolacton
• 英文别名: N-butyl-2-oxotetrahydrofuran-3-carboxamide；2-oxo-tetrahydro-furan-3-carboxylic acid butylamide；N-butyl-2-oxooxolane-3-carboxamide
• CAS: 52217-14-8
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: NNFGQLAZZSCGMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-(n-Butylcarbamoyl)-γ-butyrolacton 在 sodium azide 、 三氟甲磺酸酐 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以35%的产率得到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
• 作为产物：
  描述：

  2-氧代四氢呋喃-3-羧酸 、 正丁胺 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到α-(n-Butylcarbamoyl)-γ-butyrolacton
  参考文献：
  名称：

  AHL依赖的群体感应抑制：α-（N-烷基-羧酰胺）-γ-丁内酯和α-（N-烷基-磺酰胺）-γ-丁内酯的合成和生物学评估

  摘要：

  已经研究了新的N-酰基高丝氨酸内酯（AHL）类似物，其中酰胺功能被一种反向酰胺取代，作为AHL QS调节剂。该系列化合物由α-（N-烷基-羧酰胺）-γ-丁内酯，α-（N-烷基-磺酰胺）-γ-丁内酯和2-（N-烷基-羧酰胺）-环戊酮和环戊醇组成。大多数活性化合物对LuxR的拮抗活性均达到30μM。

  DOI：

  10.1016/j.bmcl.2011.09.010

文献信息

• AHL-dependent quorum sensing inhibition: Synthesis and biological evaluation of α-(N-alkyl-carboxamide)-γ-butyrolactones and α-(N-alkyl-sulfonamide)-γ-butyrolactones
  作者：Mohamed Boukraa、Mohamad Sabbah、Laurent Soulère、Mohamed L. El Efrit、Yves Queneau、Alain Doutheau

  DOI：10.1016/j.bmcl.2011.09.010

  日期：2011.11

  N-acylhomoserine lactone (AHL) analogues in which the amide function is replaced by a reverse-amide one have been studied as AHL QS modulators. The series of compounds consists of α-(N-alkyl-carboxamide)-γ-butyrolactones, α-(N-alkyl-sulfonamide)-γ-butyrolactones, and 2-(N-alkyl-carboxamide)-cyclopentanones and cyclopentanols. Most active compounds exhibited antagonist activities against LuxR reaching

  已经研究了新的N-酰基高丝氨酸内酯（AHL）类似物，其中酰胺功能被一种反向酰胺取代，作为AHL QS调节剂。该系列化合物由α-（N-烷基-羧酰胺）-γ-丁内酯，α-（N-烷基-磺酰胺）-γ-丁内酯和2-（N-烷基-羧酰胺）-环戊酮和环戊醇组成。大多数活性化合物对LuxR的拮抗活性均达到30μM。
• 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.