N-(2-oxooxolan-3-yl)heptane-1-sulfonamide | 797059-78-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-oxooxolan-3-yl)heptane-1-sulfonamide
• CAS: 797059-78-0
• 化学式: C₁₁H₂₁NO₄S
• 分子量: 263.358
• InChiKey: MKRJJWPHQNIBQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  α-氨基-γ-丁内酯氢溴酸盐 、 N-(2-oxooxolan-3-yl)heptane-1-sulfonamide 在 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以50%的产率得到N-(2-Oxo-tetrahydro-furan-3-yl)-C-phenyl-methanesulfonamide
  参考文献：
  名称：

  N-Sulfonyl homoserine lactones as antagonists of bacterial quorum sensing

  摘要：

  A series of 11 new analogues of N-acylhomoserine lactones in which the carboxamide bond was replaced by a sulfonamide one, has been synthesised. These compounds were evaluated for their ability to competitively inhibit the action of 3-oxohexanoyl-L-homoserine lactone, the natural ligand of the quorum sensing transcriptional regulator LuxR, which in turn activates expression of bioluminescence in the model bacterium Vibrio fischeri. Several compounds were found to display antagonist activity. Molecular modeling suggests that the latter prevent a cascade of structural rearrangements necessary for the formation of the active LuxR dimer. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.088
• 作为产物：
  描述：

  sodium heptanesulfonate 在 4-二甲氨基吡啶 、 氯化亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 28.0h， 生成 N-(2-oxooxolan-3-yl)heptane-1-sulfonamide
  参考文献：
  名称：

  N-Sulfonyl homoserine lactones as antagonists of bacterial quorum sensing

  摘要：

  A series of 11 new analogues of N-acylhomoserine lactones in which the carboxamide bond was replaced by a sulfonamide one, has been synthesised. These compounds were evaluated for their ability to competitively inhibit the action of 3-oxohexanoyl-L-homoserine lactone, the natural ligand of the quorum sensing transcriptional regulator LuxR, which in turn activates expression of bioluminescence in the model bacterium Vibrio fischeri. Several compounds were found to display antagonist activity. Molecular modeling suggests that the latter prevent a cascade of structural rearrangements necessary for the formation of the active LuxR dimer. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.088

文献信息

• N-Sulfonyl homoserine lactones as antagonists of bacterial quorum sensing
  作者：Sandra Castang、Bernard Chantegrel、Christian Deshayes、René Dolmazon、Patrice Gouet、Richard Haser、Sylvie Reverchon、William Nasser、Nicole Hugouvieux-Cotte-Pattat、Alain Doutheau

  DOI：10.1016/j.bmcl.2004.07.088

  日期：2004.10

  A series of 11 new analogues of N-acylhomoserine lactones in which the carboxamide bond was replaced by a sulfonamide one, has been synthesised. These compounds were evaluated for their ability to competitively inhibit the action of 3-oxohexanoyl-L-homoserine lactone, the natural ligand of the quorum sensing transcriptional regulator LuxR, which in turn activates expression of bioluminescence in the model bacterium Vibrio fischeri. Several compounds were found to display antagonist activity. Molecular modeling suggests that the latter prevent a cascade of structural rearrangements necessary for the formation of the active LuxR dimer. (C) 2004 Elsevier Ltd. All rights reserved.