N-十一烷酰基-L-高丝氨酸内酯 | 216596-71-3

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丝氨酸类衍生物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-十一烷酰基-L-高丝氨酸内酯
• 英文名称: N-undecanoyl-L-Homoserine lactone
• 英文别名: N-[(3S)-2-oxooxolan-3-yl]undecanamide
• CAS: 216596-71-3
• 化学式: C₁₅H₂₇NO₃
• 分子量: 269.384
• InChiKey: YAWJNUREPGJHSG-ZDUSSCGKSA-N

物化性质

• 溶解度：
  DMF：20mg/mL；二甲基亚砜：25mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  十一烷酰氯 、 (S)-α-氨基-γ-丁内酯 盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 N-十一烷酰基-L-高丝氨酸内酯
  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

• Apoptosis inducer and method of screening for a substance inhibiting acylated homoserine lactone
  申请人：Nomura, Nobuhiko

  公开号：EP1442742A1

  公开（公告）日：2004-08-04

  The present invention relates to an Akt inhibitor comprising a compound represented by formula I: [wherein R is C4-30 linear or branched acyl, which may be substituted.] The present invention further relates to a method of screening for a substance inhibiting acylated homoserine lactone by culturing animal cells with a test substance in the presence of acylated homoserine lactone represented by the above formula I, and then detecting inhibition of Akt activity or inhibition of the survival signalling pathway in which Akt is involved in the cells.

  本发明涉及一种 Akt 抑制剂，包括由式 I 所代表的化合物： [其中R为C4-30直链或支链酰基，可被取代。] 本发明进一步涉及一种筛选抑制酰化高丝氨酸内酯的物质的方法，该方法是在有上述式I代表的酰化高丝氨酸内酯存在的情况下，用试验物质培养动物细胞，然后检测细胞中Akt活性的抑制情况或Akt参与的生存信号通路的抑制情况。
• INHIBITION OF MATURATION OF DENTAL BIOFILM AND CARIOGENIC PROPERTIES
  申请人：KONINKLIJKE PHILIPS N.V.

  公开号：US20170252278A1

  公开（公告）日：2017-09-07

  The present invention relates to a small molecule inhibitor for use in the prevention of maturation of dental plaque biofilms. A further application may be the reduction of the risk for diseases associated with functions that derive from matured dental plaque biofilms. The invention also relates to the use of an effective amount of a small molecule inhibitor in a cosmetic product for the prevention of maturation of dental biofilms. The present invention also relates to oral compositions comprising an effective amount of a small molecule inhibitor suitable for the prevention of maturation of dental plaque biofilms. The present invention further relates to a device for application of oral compositions further comprising an oral composition comprising an effective amount of a small molecule inhibitor suitable for the prevention of maturation of dental plaque biofilms.
• US7537906B2
  申请人：——

  公开号：US7537906B2

  公开（公告）日：2009-05-26