N-3-hydroxytetradecanoyl homoserine lactone | 364749-99-5

• 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
• 英文名称: N-3-hydroxytetradecanoyl homoserine lactone
• 英文别名: 3-hydroxytetradecanoyl-homoserine lactone；Tetradecanamide, 3-hydroxy-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-；3-hydroxy-N-[(3S)-2-oxooxolan-3-yl]tetradecanamide
• CAS: 364749-99-5
• 化学式: C₁₈H₃₃NO₄
• 分子量: 327.464
• InChiKey: IKQUESGRCDRZTI-LYKKTTPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(3-氧代十四烷酰基)-L-高丝氨酸内酯 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 N-3-hydroxytetradecanoyl homoserine lactone
  参考文献：
  名称：

  鉴定和定量 ñ内标物的小规模合成和基质辅助激光解吸/电离质谱法参与细菌通讯的-酰基高丝氨酸内酯

  摘要：

  ñ酰基高丝氨酸内酯（AHL）是参与许多革兰氏阴性细菌群体感应的小信号分子，在生物膜形成和发病机理中起着重要作用。当前用于AHL鉴定和定量的分析方法需要耗时的样品制备步骤，并且由于缺乏适当的标准而受阻。通过针对AHL分析的快速，直接方法，我们研究了基质辅助激光解吸/电离飞行时间质谱（MALDI-TOF MS）的适用性。测试了合适的MALDI基质（包括晶体和离子液体基质），并研究了碰撞诱导解离MS / MS中不同AHL的裂解，从而提供了有关特征性标记碎片离子的信息。采用小规模的合成协议，我们建立了一种通用且具有成本效益的程序，可快速生成同位素标记的AHL标准品，而无需大量纯化即可使用，并能产生准确的标准曲线。可以在低皮摩尔范围内进行定量分析，对于不同的AHL，定量下限可达到1-5 pmol。所开发的方法已成功地用于定量的小批量培养上清液的MALDI MS分析。铜绿假单胞菌。 在新窗口中打开图像

  DOI：

  10.1007/s13361-017-1777-x

文献信息

• Immunosuppressant n-acyles homoserine lactones
  申请人：——

  公开号：US20030171371A1

  公开（公告）日：2003-09-11

  New N-acyl homoserine lactone compounds of the formula (I) in whichR is an acyl group of the formula (II) wherein one of R 1 and R 2 is H and the other is selected from OR 4 , SR 4 and NHR 4 , wherein R 4 is H or 1-6C alkyl, or R 1 and R 2 together with the carbon atom to which they are joined form a keto group, and R 3 containing from 8 to 11 carbon atoms and is optionally substituted by one or more substituent groups selected from halo, 1-6C alkoxy, carboxy, 1-6C alkoxycarbonyl, carbamoyl optionally mono- or disubstituted at the N atom by 1-6C alkyl and NR 5 R 6 wherein each of R 5 and R 6 is selected from H and 1-6C alkyl or R 5 and R 6 together with the N atom form a morpholino or piperazino group, or and enantiomer thereof, with the proviso that R is not a 3-oxododecanoyl group, having immuosuppressant properties are disclosed. The compounds are shown to have an inhibitory effect on lymphocyte proliferation and down-regulate TNF-&agr; secretion by monocytes/macrophages in the animal body, including the human body. Pharmaceutical composition comprising N-acyl homoserine lactones are also described. 1

  公开了式(I)的新的N-酰基高丝氨酸内酯化合物，其中R是式(II)的酰基，其中R1和R2中的一个为H，另一个选择自OR4、SR4和NHR4，其中R4为H或1-6C烷基，或者R1和R2与它们结合的碳原子一起形成酮基，而R3含有8至11个碳原子，并且可以被一个或多个取代基选自卤素、1-6C烷氧基、羧基、1-6C烷氧羰基、在N原子上可能被1-6C烷基单独或二取代的氨基和NR5R6，其中R5和R6中的每一个选择自H和1-6C烷基或R5和R6与N原子一起形成吗啡环或哌嗪环，或其对映体，但R不是3-氧代十二酰基基团。这些化合物具有免疫抑制特性，已经表明这些化合物对淋巴细胞增殖具有抑制作用，并且在动物体内，包括人体内，下调单核细胞/巨噬细胞的TNF-α分泌。还描述了包含N-酰基高丝氨酸内酯的制药组合物。
• Synergistic compositions of n-acylhomoserine lactones and 4-quinolones
  申请人：——

  公开号：US20040198978A1

  公开（公告）日：2004-10-07

  A composition having immunosuppressant activity comprises at least one compound of the formula (I) in which R is an acyl group of the formula (II) wherein one of R 1 and R 2 is H and the other is selected from OR 4 , SR 4 and NHR 4 , wherein R 4 is H or 1-6C alkyl, or R 1 and R 2 together with the carbon atom to which they are joined form a keto group, and R 3 is a straight or branched chain, saturated or unsaturated aliphatic hydrocarbyl group containing from 8 to 11 carbon atoms and is optionally substituted by one or more substituent groups selected from halo, 1-6C alkoxy, carboxy, 1-6C alkoxycarbonyl and NR 5 R 6 wherein each of R 5 and R 6 is selected from H and 1-6C alkyl or R 5 and R 6 together with the N atom form a morpholino or piperazino group, or any enantiomer thereof; and at least one compound of the formula (III): wherein R 7 is a straight or branched chain, saturated or ethylenically-unsaturated aliphatic hydrocarbyl group containing from 1 to 18 carbon atoms which may optionally be substituted by one or more substituent groups selected from halo, 1-6C alkoxy, carboxy, 1-6C alkoxycarbonyl and NR 12 R 13 , wherein each of R 12 and R 13 is independently selected from H and 1-6C alkyl or R 12 and R 13 together with the N atom to which they are attached form a saturated heterocyclic group selected from piperidino, piperazino and morpholino; R 8 is a group selected from H, —OH, halo, —CHO, —CO 2 H and CONHR 14 wherein R 14 is H or a 1-6C alkyl; each of R 9 , R 10 and R 11 is independently selected from H, —CH 3 , —OCH 3 and halo; or a non-toxic pharmaceutically-acceptable salt thereof. The determined immunosuppressant activity of the composition is greater than the sum of the activities of the individual components of the composition when determined separately. 1

  具有免疫抑制活性的组合物包括公式（I）中至少一种化合物，其中R是公式（II）的酰基，其中R1和R2中的一个是H，另一个选自OR4，SR4和NHR4，其中R4是H或1-6C烷基，或者R1和R2与它们连接的碳原子形成酮基，R3是含有8至11个碳原子的直链或支链、饱和或不饱和的脂肪族羟基烷基，可选地被一个或多个取代基选自卤素，1-6C烷氧基，羧基，1-6C烷氧羰基和NR5R6取代，其中每个R5和R6选自H和1-6C烷基或R5和R6与N原子形成吗啉或哌嗪基团，或其任何对映体；以及公式（III）中的至少一种化合物：其中R7是含有1至18个碳原子的直链或支链、饱和或乙烯不饱和的脂肪族羟基烷基，可以选择地被一个或多个取代基选自卤素，1-6C烷氧基，羧基，1-6C烷氧羰基和NR12R13取代，其中每个R12和R13独立地选自H和1-6C烷基或R12和R13与它们附着的N原子形成选自哌啶基，哌嗪基和吗啉的饱和杂环基；R8是选自H，—OH，卤素，—CHO，—CO2H和CONHR14的基团，其中R14是H或1-6C烷基；每个R9、R10和R11独立地选自H、—CH3、—OCH3和卤素；或其非毒性药物可接受盐。当单独测定时，组合物的确定免疫抑制活性大于组合物各个组分的活性之和。
• Synthetic Analogues of the Bacterial Signal (Quorum Sensing) Molecule <i>N</i>-(3-Oxododecanoyl)-<scp>l</scp>-homoserine Lactone as Immune Modulators
  作者：Siri Ram Chhabra、Chris Harty、Doreen S. W. Hooi、Mavis Daykin、Paul Williams、Gary Telford、David I. Pritchard、Barrie W. Bycroft

  DOI：10.1021/jm020909n

  日期：2003.1.1

  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.
• SYNERGISTIC COMPOSITIONS OF N-ACYLHOMOSERINE LACTONES AND 4-QUINOLONES
  申请人：THE UNIVERSITY OF NOTTINGHAM

  公开号：EP1404315B1

  公开（公告）日：2004-11-03
• US7371779B2
  申请人：——

  公开号：US7371779B2

  公开（公告）日：2008-05-13