N1-(2-(2-ethoxyethoxy)ethyl)-N3-((1R,2S)-2-hydroxycyclopentyl)malonamide | 1298023-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N1-(2-(2-ethoxyethoxy)ethyl)-N3-((1R,2S)-2-hydroxycyclopentyl)malonamide
• 英文别名: N-[2-(2-ethoxyethoxy)ethyl]-N'-[(1R,2S)-2-hydroxycyclopentyl]propanediamide
• CAS: 1298023-65-0
• 化学式: C₁₄H₂₆N₂O₅
• 分子量: 302.371
• InChiKey: RBBCIJQMICXDHV-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二乙二醇乙醚 在 sodium tetrahydroborate 、 hydrazine hydrate 、 偶氮二甲酸二异丙酯 、 palladium on carbon 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三苯基膦 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 65.83h， 生成 N1-(2-(2-ethoxyethoxy)ethyl)-N3-((1R,2S)-2-hydroxycyclopentyl)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