ethyl 4-aza-4-methyl-3-oxododecanoate | 957550-66-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-aza-4-methyl-3-oxododecanoate
• 英文别名: Ethyl 3-[methyl(octyl)amino]-3-oxopropanoate
• CAS: 957550-66-2
• 化学式: C₁₄H₂₇NO₃
• 分子量: 257.373
• InChiKey: WONVFCMKIWISSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-aza-4-methyl-3-oxododecanoate 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 以93%的产率得到3-(methyl(octyl)amino)-3-oxopropanoic acid
  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：

  N-甲基辛胺 、 氯甲酰乙酸乙酯 以 二氯甲烷 为溶剂， 以97%的产率得到ethyl 4-aza-4-methyl-3-oxododecanoate
  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

• SUBSTITUTED N-ACYL HOMOSERINE LACTONES
  申请人：THE SECRETARY OF STATE FOR DEFENCE

  公开号：EP2044046B1

  公开（公告）日：2009-10-21
• US8049020B2
  申请人：——

  公开号：US8049020B2

  公开（公告）日：2011-11-01
• [EN] SUBSTITUTED N-ACYL HOMOSERINE LACTONES<br/>[FR] LACTONES N-ACYLE HOMOSÉRINE SUBSTITUÉES
  申请人：UNIV NOTTINGHAM

  公开号：WO2007135466A2

  公开（公告）日：2007-11-29

  [EN] The substituted N-acyl homoserine lactones have the formula (I) wherein R is a saturated or unsaturated straight chain or branched chain aliphatic hydrocarbyl group containing from 5 to 14 carbon atoms; R² is H or a 1-4C alkyl group; R³ is H or F; and any enantiomer thereof. These compounds exhibit immunosuppressant activity while exhibiting reduced biosensor (autoinducer) activity compared to known N-acyl homoserine lactones.
  [FR] L'invention concerne des lactones N-acyle homosérine substituées de formule I (Formule I), dans laquelle R représente un groupement hydrocarbyle aliphatique à chaîne linéaire ou ramifiée, saturé ou insaturé, contenant de 5 à 14 atomes de carbone; R² représente H ou un groupement alkyle ayant de 1 à 4 atomes de carbone; R³ représente H ou F; et leurs énantiomères. Ces composés présentent une activité d'immunosuppresseurs tout en ayant une activité de biocapteurs (autoinducteurs) réduite en comparaison des lactones N-acyle homosérine connues.
• 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.