3-oxo-dodecanamide | 252361-34-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-oxo-dodecanamide
• 英文别名: Dodecanamide, 3-oxo-；3-oxododecanamide
• CAS: 252361-34-5
• 化学式: C₁₂H₂₃NO₂
• 分子量: 213.32
• InChiKey: FZJHPORKYNLZAD-UHFFFAOYSA-N

物化性质

• 沸点：
  356.0±25.0 °C(Predicted)
• 密度：
  0.950±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  正癸酸 在 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 5.0h， 生成 3-oxo-dodecanamide
  参考文献：
  名称：

  Synthetic Analogues of the Bacterial Signal (Quorum Sensing) Molecule N-(3-Oxododecanoyl)-l-homoserine Lactone as Immune Modulators

  摘要：

  Comparative immune modulatory activity for a range of synthetic analogues of a Pseudomonas aeruginosa signal molecule, N-(3-oxododecanoyl)-L-homoserine lactone (3O, C-12-HSL), is described. Twenty-four single or combination systematic alterations of the structural components of 3O, C12-HSL were introduced as described. Given the already defined immunological profile of the parent compound, 3O, C12-HSL, these compounds were assayed for their ability to inhibit murine and human leucocyte proliferation and TNF-alpha secretion by lipopolysaccharide (LPS) stimulated human leucocytes in order to provide an initial structure-activity profile. From IC50 values obtained with a murine splenocyte proliferation assay, it is apparent that acylated L-homoserine lactones with an 11-13 C side chain containing either a 3-oxo or a 3-hydroxy group are optimal structures for immune suppressive activity. These derivatives of 3O, C-12-HSL with monounsaturation and/or a terminal nonpolar substituent on the side chain were also potent immune suppressive agents. However, structures lacking the homoserine lactone ring, structures lacking the L-configuration at the chiral center, and those with polar substituents were essentially devoid of activity. The ability of compounds selected from the optimal activity range to modulate mitogen-driven human peripheral blood mononuclear cell proliferation and LPS-induced TNF-alpha secretion indicates the suitability of these compounds for further investigation in relation to their molecular mechanisms of action in TNF-alpha driven immunological diseases, particularly autoimmune diseases such as psoriasis, rheumatoid arthritis, and type 1 (autoimmune) diabetes.

  DOI：

  10.1021/jm020909n

文献信息

• Enamine-Based Domino Strategy for C-Acylation/Deacetylation of Acetoacetamides: A Practical Synthesis of β-Keto Amides
  作者：Plamen Angelov

  DOI：10.1055/s-0029-1219836

  日期：2010.5

  A practical three-step route for C-acylation/deacetylation of acetoacetamides is described. Initial enamination of the acetoacetamides with Boc-monoprotected ethylenediamine provides β-enamino amides, which are acylated at the α-carbon with excellent selectivity. The C-acylated derivatives undergo domino fragmentation in acidic media to give the corresponding α-Keto amides accompanied by 2-methyl-4

  描述了乙酰乙酰胺的 C-酰化/脱乙酰化的实用三步路线。乙酰乙酰胺与 Boc 单保护乙二胺的初始烯化提供 β-烯氨基酰胺，其在 α-碳上以优异的选择性酰化。C-酰化衍生物在酸性介质中发生多米诺断裂，得到相应的α-酮酰胺，并伴随有 2-甲基-4,5-二氢-1H-咪唑。
• INHIBITORS OF BIOFILM FORMATION OF GRAM-POSITIVE AND GRAM-NEGATIVE BACTERIA
  申请人：Ammendola Aldo

  公开号：US20090192192A1

  公开（公告）日：2009-07-30

  The present invention relates to the use of compounds as broad spectrum inhibitors of bacterial biofilm formation. In particular the invention refers to a family of compounds that block the quorum sensing system of Gram-negative and Gram-positive bacteria, a process for their manufacture, pharmaceutical compositions containing them and to their use for the treatment and prevention of bacterial damages and diseases, in particular for diseases where there is an advantage in inhibiting quorum sensing regulated phenotypes of pathogens.

  本发明涉及使用化合物作为广谱细菌生物膜形成的抑制剂。具体而言，本发明涉及一系列化合物，能够阻断革兰氏阴性和革兰氏阳性细菌的群体感应系统，一种制造它们的方法，含有它们的制药组合物以及它们用于治疗和预防细菌损害和疾病的用途，特别是对于需要抑制病原体的群体感应调节表型的疾病有优势的情况。
• Quorum sensing based polymer for stimulation of biofilms and related phenotypes, and synthesis process thereof
  申请人：FIB-SOL Life Technologies Private Limited

  公开号：US10988571B2

  公开（公告）日：2021-04-27

  The invention relates to the synthesis and process thereof of a Quorum Sensing (QS) based polymer formed by the process of ring opening polymerization/ring opening copolymerization. The formed homopolymer or heteropolymer or copolymer displays increased half-life, bioactivity and biostability in stimulating the microbial quorum sensing in a predetermined microbial population.

  本发明涉及通过开环聚合/开环共聚过程形成的基于法定人数感应（QS）的聚合物的合成及其工艺。所形成的均聚物或杂聚物或共聚物在刺激预定微生物群的微生物法定量感应方面显示出更长的半衰期、生物活性和生物稳定性。
• QUORUM SENSING BASED POLYMER FOR STIMULATION OF BIOFILMS AND RELATED PHENOTYPES, AND SYNTHESIS PROCESS THEREOF
  申请人：FIB-SOL Life Technologies Private Limited

  公开号：US20200031989A1

  公开（公告）日：2020-01-30

  The invention relates to the synthesis and process thereof of a Quorum Sensing (QS) based polymer formed by the process of ring opening polymerization/ring opening copolymerization. The formed homopolymer or heteropolymer or copolymer displays increased half-life, bioactivity and biostability in stimulating the microbial quorum sensing in a predetermined microbial population.
• ANALOGUES OF N-ACYL-HOMOSERINE LACTONES AND PHARMACEUTICAL COMPOSITION COMPRISING SAME
  申请人：SORBONNE UNIVERSITE

  公开号：US20220411397A1

  公开（公告）日：2022-12-29

  The present invention relates to analogues of N-acyl homoserine lactones (AHLs) and pharmaceutical compositions comprising same. The invention also relates to their use in the treatment of inflammatory diseases of the epithelium.