3-羟基-n-((s)-2-氧代四氢呋喃-3-基)十二酰胺 | 216596-73-5

• 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
• 中文名称: 3-羟基-n-((s)-2-氧代四氢呋喃-3-基)十二酰胺
• 英文名称: N-(3-hydroxy-dodecanoyl)-L-homoserine lactone
• 英文别名: 3-Hydroxy-N-((S)-2-oxotetrahydrofuran-3-yl)dodecanamide；3-hydroxy-N-[(3S)-2-oxooxolan-3-yl]dodecanamide
• CAS: 216596-73-5
• 化学式: C₁₆H₂₉NO₄
• 分子量: 299.411
• InChiKey: RGTXFFYJJNWEPV-KZUDCZAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3-羟基-n-((s)-2-氧代四氢呋喃-3-基)十二酰胺 反应 2.0h， 以97%的产率得到1-oxo-1-((S)-2-oxotetrahydrofuran-3-ylamino)dodecan-3-yl acetate
  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：

  正癸酸 在 盐酸 、 4-二甲氨基吡啶 、 sodium cyanoborohydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 3-羟基-n-((s)-2-氧代四氢呋喃-3-基)十二酰胺
  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

• Enzymatic Method for N-Acyl Homoserine Lactones Synthesis Using Immobilized Candida antarctica Lipase
  作者：Juan Vázquez-Martínez、Edgar Nieto-Álvarez、Enrique Ramírez-Chávez、Jorge Molina-Torres

  DOI：10.1007/s10562-017-2261-8

  日期：2018.1

  An enzymatic method to produce N-acyl homoserine lactones (AHLs) is described. This report represents the first example of the synthesis of bioactive AHLs using immobilized Candida antarctica lipase as the catalyst. The reaction yields, evaluated by GC-EIMS, ranged from 6 to 99%.Graphical Abstract

  描述了一种生产 N-酰基高丝氨酸内酯 (AHL) 的酶促方法。本报告代表了使用固定化南极念珠菌脂肪酶作为催化剂合成生物活性 AHLs 的第一个例子。GC-EIMS 评估的反应产率为 6% 至 99%。 图形摘要
• 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、—O 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。
• Wound packing material comprising chemoeffector
  申请人：CHEMOKIND, INC.

  公开号：US11273077B2

  公开（公告）日：2022-03-15

  A wound packing material, particularly suitable for use in negative pressure wound therapy, comprising a porous material admixed with a chemoattractant. This disclosure further provides methods of manufacturing the wound packing material, and therapeutic methods of using the wound packing material.

  一种伤口填料，特别适用于负压伤口治疗，包括一种多孔材料和一种趋化吸引剂。本公开进一步提供了制造伤口填料的方法，以及使用伤口填料的治疗方法。
• 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.