Ethyl 3-(nonylamino)-3-oxopropanoate | 1325232-02-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 3-(nonylamino)-3-oxopropanoate
• CAS: 1325232-02-7
• 化学式: C₁₄H₂₇NO₃
• 分子量: 257.373
• InChiKey: YXKBEXCCPUDXQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  Ethyl 3-(nonylamino)-3-oxopropanoate 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 20.0h， 生成 (S)-N1-nonyl-N3-(2-oxotetrahydrofuran-3-yl)malonamide
  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：

  壬胺 、 氯甲酰乙酸乙酯 以 二氯甲烷 为溶剂， 以66%的产率得到Ethyl 3-(nonylamino)-3-oxopropanoate
  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

文献信息

• 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.