2-(nonylsulfinyl)acetic acid

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: 2-(nonylsulfinyl)acetic acid
• 英文别名: (nonane-1-sulfinyl)-acetic acid；(Nonan-1-sulfinyl)-essigsaeure；2-Nonylsulfinylacetic acid
• 化学式: C₁₁H₂₂O₃S
• 分子量: 234.36
• InChiKey: ZTTDIRQYMHWFKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  73.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(nonylsulfinyl)acetic acid 、 (S)-α-氨基-γ-丁内酯 盐酸盐 在 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以50%的产率得到2-(nonylsulfinyl)-N-((S)-2-oxotetrahydrofuran-3-yl)acetamide
  参考文献：
  名称：

  Immunosuppressive but Non-LasR-Inducing Analogues of the Pseudomonas aeruginosa Quorum-Sensing Molecule N-(3-Oxododecanoyl)-l-homoserine Lactone

  摘要：

  The Pseudomonas aeruginosa quorum-sensing molecule N-(3-oxododecanoyl)-l-homoserine lactone (1) is involved not only in bacterial activation but also in subversion of the host immune system, and this compound might thus be used as a template to design immunosuppressive agents, provided derivatives devoid of quorum-sensing activity could be discovered. By use of a leukocyte proliferation assay and a newly developed bioluminescent P. aeruginosa reporter assay, systematic modification of 1 allowed us to delineate the bacterial LasR-induction and host immunosuppressive activities. The main determinant is replacement of the methylene group proximal to the beta-ketoamide in the acyl chain of 1 with functions containing heteroatoms, especially an NH group. This modification can be combined with replacement of the homoserine lactone system in 1 with stable cyclic groups. For example, we found the simple compound N(1)-(5-chloro-2-hydroxyphenyl)-N(3)-octylmalonamide (25d) to be over twice as potent as 1 as an immune suppressor while displaying LasR-induction antagonist activity.

  DOI：

  10.1021/jm2001019
• 作为产物：
  描述：

  壬烯 在 盐酸 、 溴 、 溶剂黄146 作用下， 生成 2-(nonylsulfinyl)acetic acid
  参考文献：
  名称：

  Smith; Hernestam, Acta Chemica Scandinavica (1947), 1954, vol. 8, p. 1111,1116,1118

  摘要：

  DOI：

文献信息

• Smith; Hernestam, Acta Chemica Scandinavica (1947), 1954, vol. 8, p. 1111,1116,1118
  作者：Smith、Hernestam

  DOI：——

  日期：——
• Immunosuppressive but Non-LasR-Inducing Analogues of the <i>Pseudomonas aeruginosa</i> Quorum-Sensing Molecule <i>N</i>-(3-Oxododecanoyl)-<scp>l</scp>-homoserine Lactone
  作者：Gopal P. Jadhav、Siri Ram Chhabra、Gary Telford、Doreen S. W. Hooi、Karima Righetti、Paul Williams、Barrie Kellam、David I. Pritchard、Peter M. Fischer

  DOI：10.1021/jm2001019

  日期：2011.5.12

  The Pseudomonas aeruginosa quorum-sensing molecule N-(3-oxododecanoyl)-l-homoserine lactone (1) is involved not only in bacterial activation but also in subversion of the host immune system, and this compound might thus be used as a template to design immunosuppressive agents, provided derivatives devoid of quorum-sensing activity could be discovered. By use of a leukocyte proliferation assay and a newly developed bioluminescent P. aeruginosa reporter assay, systematic modification of 1 allowed us to delineate the bacterial LasR-induction and host immunosuppressive activities. The main determinant is replacement of the methylene group proximal to the beta-ketoamide in the acyl chain of 1 with functions containing heteroatoms, especially an NH group. This modification can be combined with replacement of the homoserine lactone system in 1 with stable cyclic groups. For example, we found the simple compound N(1)-(5-chloro-2-hydroxyphenyl)-N(3)-octylmalonamide (25d) to be over twice as potent as 1 as an immune suppressor while displaying LasR-induction antagonist activity.