亲电酮-四烯15-氧代脂氧素A甲酯硼酸亚氨基二乙酸酯的合成
Synthesis of an Electrophilic Keto-Tetraene 15-oxo-Lipoxin A Methyl Ester a MIDA Boronate.
作者信息
Woodcock Steven R, Wendell Stacy G, Schopfer Francisco J, Freeman Bruce A
机构信息
Department of Pharmacology and Chemical Biology, University of Pittsburgh, Pittsburgh, PA USA 16260.
出版信息
Tetrahedron Lett. 2018 Sep 26;59(39):3524-3527. doi: 10.1016/j.tetlet.2018.08.014. Epub 2018 Aug 10.
Abstract
15-oxo-Lipoxin A (15-oxo- LXA) has been identified as a natural metabolite of the fatty acid signaling mediator Lipoxin A. Herein, we report a total synthesis of the methyl ester of 15-oxo-LXA to be used in investigations of potential electrophilic bioactivity of this metabolite. The methyl ester of 15-oxo-LXA was synthesized in a convergent 15 step (9 steps longest linear) sequence starting from 1-octyn-3-ol and 2-deoxy-D-ribose with Sonogashira and Suzuki cross-couplings of a MIDA boronate as key steps.
摘要
15-氧代脂氧素A（15-oxo-LXA）已被鉴定为脂肪酸信号介质脂氧素A的天然代谢产物。在此，我们报道了15-氧代-LXA甲酯的全合成，用于研究该代谢产物潜在的亲电生物活性。15-氧代-LXA甲酯是通过一个汇聚式的15步（最长线性9步）序列合成的，从1-辛炔-3-醇和2-脱氧-D-核糖开始，以MIDA硼酸酯的Sonogashira和Suzuki交叉偶联为关键步骤。
相似文献
1
Synthesis of an Electrophilic Keto-Tetraene 15-oxo-Lipoxin A Methyl Ester a MIDA Boronate.亲电酮-四烯15-氧代脂氧素A甲酯硼酸亚氨基二乙酸酯的合成
Tetrahedron Lett. 2018 Sep 26;59(39):3524-3527. doi: 10.1016/j.tetlet.2018.08.014. Epub 2018 Aug 10.
2
Lipoxin A yields an electrophilic 15-oxo metabolite that mediates FPR2 receptor-independent anti-inflammatory signaling.脂氧素A产生一种亲电的15-氧代代谢物，该代谢物介导不依赖于FPR2受体的抗炎信号传导。
J Lipid Res. 2025 Jan;66(1):100705. doi: 10.1016/j.jlr.2024.100705. Epub 2024 Nov 19.
3
Lipoxin A yields an electrophilic 15-oxo metabolite that mediates FPR2 receptor-independent anti-inflammatory signaling.脂氧素A产生一种亲电子的15-氧代代谢物，该代谢物介导不依赖于FPR2受体的抗炎信号传导。
bioRxiv. 2024 Feb 7:2024.02.06.579101. doi: 10.1101/2024.02.06.579101.
4
Pilot application of lipoxin A analog and lipoxin A receptor agonist in asthmatic children with acute episodes.脂氧素A类似物和脂氧素A受体激动剂在哮喘急性发作儿童中的初步应用。
Exp Ther Med. 2017 Sep;14(3):2284-2290. doi: 10.3892/etm.2017.4787. Epub 2017 Jul 12.
5
Use of -methyliminodiacetic acid boronate esters in suzuki-miyaura cross-coupling polymerizations of triarylamine and fluorene monomers.甲基亚氨基二乙酸硼酸酯在三芳基胺和芴单体的铃木-宫浦交叉偶联聚合反应中的应用。
J Polym Sci A Polym Chem. 2017 Sep 1;55(17):2798-2806. doi: 10.1002/pola.28682. Epub 2017 Jul 3.
6
Lipoxin A4 metabolism by differentiated HL-60 cells and human monocytes: conversion to novel 15-oxo and dihydro products.分化的HL-60细胞和人单核细胞对脂氧素A4的代谢：转化为新型15-氧代和二氢产物。
Biochemistry. 1993 Jun 29;32(25):6313-9. doi: 10.1021/bi00076a002.
7
Aspirin augments 15-epi-lipoxin A4 production by lipopolysaccharide, but blocks the pioglitazone and atorvastatin induction of 15-epi-lipoxin A4 in the rat heart.阿司匹林可增强脂多糖诱导的15-表-脂氧素A4生成，但会阻断吡格列酮和阿托伐他汀在大鼠心脏中对15-表-脂氧素A4的诱导作用。
Prostaglandins Other Lipid Mediat. 2007 Feb;83(1-2):89-98. doi: 10.1016/j.prostaglandins.2006.10.003. Epub 2006 Nov 7.
8
Carboxyboronate: A Versatile C1 Building Block.羧基硼酸盐：一种多功能的 C1 砌块。
Angew Chem Int Ed Engl. 2019 Oct 14;58(42):15148-15153. doi: 10.1002/anie.201907486. Epub 2019 Sep 10.
9
Design of lipoxin A4 stable analogs that block transmigration and adhesion of human neutrophils.阻断人中性粒细胞迁移和黏附的脂氧素A4稳定类似物的设计
Biochemistry. 1995 Nov 7;34(44):14609-15. doi: 10.1021/bi00044a041.
10
Synthesis of aromatic lactone analogues of Lipoxin A4.合成脂氧素 A4 的芳香内酯类似物。
BMC Res Notes. 2022 Feb 9;15(1):30. doi: 10.1186/s13104-022-05917-4.
引用本文的文献
1
Lipoxin A yields an electrophilic 15-oxo metabolite that mediates FPR2 receptor-independent anti-inflammatory signaling.脂氧素A产生一种亲电的15-氧代代谢物，该代谢物介导不依赖于FPR2受体的抗炎信号传导。
J Lipid Res. 2025 Jan;66(1):100705. doi: 10.1016/j.jlr.2024.100705. Epub 2024 Nov 19.
2
Lipoxin A yields an electrophilic 15-oxo metabolite that mediates FPR2 receptor-independent anti-inflammatory signaling.脂氧素A产生一种亲电子的15-氧代代谢物，该代谢物介导不依赖于FPR2受体的抗炎信号传导。
bioRxiv. 2024 Feb 7:2024.02.06.579101. doi: 10.1101/2024.02.06.579101.
3
Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm.钯催化的交叉偶联反应：关于催化剂用量描述符mol%和ppm的重要性
Org Process Res Dev. 2022 Aug 19;26(8):2240-2269. doi: 10.1021/acs.oprd.2c00051. Epub 2022 Jul 11.
4
A Stereocontrolled Total Synthesis of Lipoxin B4 and its Biological Activity as a Pro-Resolving Lipid Mediator of Neuroinflammation.立体控制全合成脂氧素 B4 及其作为神经炎症促解决脂质介质的生物学活性。
Chemistry. 2022 Jun 21;28(35):e202200360. doi: 10.1002/chem.202200360. Epub 2022 May 19.
5
Electrophilic characteristics and aqueous behavior of fatty acid nitroalkenes.脂肪酸硝基烯烃的亲电特性及水相行为
Redox Biol. 2021 Jan;38:101756. doi: 10.1016/j.redox.2020.101756. Epub 2020 Oct 12.
本文引用的文献
1
Synopsis of arachidonic acid metabolism: A review.花生四烯酸代谢综述
J Adv Res. 2018 Mar 13;11:23-32. doi: 10.1016/j.jare.2018.03.005. eCollection 2018 May.
2
Unexpected Alkene Isomerization during Iterative Cross-Coupling To Form Hindered, Electron-Deficient Trienes.在迭代交叉偶联过程中形成受阻、缺电子三烯时出现意外的烯烃异构化。
Org Lett. 2018 Jun 1;20(11):3151-3155. doi: 10.1021/acs.orglett.8b00809. Epub 2018 May 21.
3
Total Synthesis of Resolvin D5.解析：“Total Synthesis of Resolvin D5”为标题，可保留英文，中文译文置于其后。
**译文**：Resolvin D5 的全合成。
J Org Chem. 2017 Feb 17;82(4):2032-2039. doi: 10.1021/acs.joc.6b02870. Epub 2017 Jan 30.
4
In Vivo Availability of Pro-Resolving Lipid Mediators in Oxazolone Induced Dermal Inflammation in the Mouse.在恶唑酮诱导的小鼠皮肤炎症中促消退脂质介质的体内可用性
PLoS One. 2015 Nov 23;10(11):e0143141. doi: 10.1371/journal.pone.0143141. eCollection 2015.
5
Selective activation/coupling of polyhalogenated nucleophiles in ni/cr-mediated reactions: synthesis of c1-c19 building block of halichondrin bs.镍/铬介导反应中多卤代亲核试剂的选择性活化/偶联：海鞘素 bs 的 C1-C19 砌块的合成。
J Am Chem Soc. 2015 May 20;137(19):6219-25. doi: 10.1021/jacs.5b03498. Epub 2015 May 11.
6
15-Hydroxyprostaglandin dehydrogenase generation of electrophilic lipid signaling mediators from hydroxy ω-3 fatty acids.15-羟基前列腺素脱氢酶由羟基ω-3脂肪酸生成亲电子脂质信号介质。
J Biol Chem. 2015 Feb 27;290(9):5868-80. doi: 10.1074/jbc.M114.635151. Epub 2015 Jan 12.
7
Determination of ω-6 and ω-3 PUFA metabolites in human urine samples using UPLC/MS/MS.使用超高效液相色谱-串联质谱法测定人尿液样本中的ω-6和ω-3多不饱和脂肪酸代谢物。
Anal Bioanal Chem. 2015 Feb;407(6):1625-39. doi: 10.1007/s00216-014-8412-5. Epub 2015 Jan 11.
8
15-Oxoeicosatetraenoic acid is a 15-hydroxyprostaglandin dehydrogenase-derived electrophilic mediator of inflammatory signaling pathways.15-氧代二十碳四烯酸是一种由15-羟基前列腺素脱氢酶衍生的炎症信号通路亲电介质。
Chem Biol Interact. 2015 Jun 5;234:144-53. doi: 10.1016/j.cbi.2014.10.029. Epub 2014 Nov 4.
9
Pro-resolving lipid mediators are leads for resolution physiology.促炎消退脂质介质是解决生理学的研究线索。
Nature. 2014 Jun 5;510(7503):92-101. doi: 10.1038/nature13479.
10
Total synthesis of the lipid mediator PD1n-3 DPA: configurational assignments and anti-inflammatory and pro-resolving actions.脂质介质 PD1n-3 DPA 的全合成：构象分配及抗炎和促解决作用。
J Nat Prod. 2014 Apr 25;77(4):910-6. doi: 10.1021/np4009865. Epub 2014 Feb 27.
Zotero 插件