从亚硝胺 Diels-Alder 化学出发合成新型噁唑烷酮并研究其抗菌活性。
Syntheses and antibacterial activity studies of new oxazolidinones from nitroso Diels-Alder chemistry.
机构信息
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA.
出版信息
Bioorg Med Chem Lett. 2010 Feb 1;20(3):1302-5. doi: 10.1016/j.bmcl.2009.10.018. Epub 2009 Oct 8.
Abstract
A series of novel oxazolidinone antibiotics having [2.2.1] and [2.2.2] bicyclic oxazine moieties at the C-5 side chain of the A-ring was synthesized by nitroso Diels-Alder reactions, from three linezolid analogs containing morpholine, piperazine and thiomorpholine, respectively, as the C-ring components. Subsequent N-O bond cleavage generated oxazolidinones with 4-amino cyclo-2-en-1-ol substituents. The in vitro antibacterial activities of these oxazolidinone analogs were evaluated.
摘要
通过硝基亚胺 Diels-Alder 反应，从三个分别含有吗啉、哌嗪和硫代吗啉作为 C 环组成部分的利奈唑胺类似物中合成了一系列具有[2.2.1]和[2.2.2]双环氧嗪环部分的新型恶唑烷酮抗生素，位于 A 环 C-5 侧链上。随后 N-O 键的断裂生成了具有 4-氨基环-2-烯-1-醇取代基的恶唑烷酮。评估了这些恶唑烷酮类似物的体外抗菌活性。
相似文献
1
Syntheses and antibacterial activity studies of new oxazolidinones from nitroso Diels-Alder chemistry.从亚硝胺 Diels-Alder 化学出发合成新型噁唑烷酮并研究其抗菌活性。
Bioorg Med Chem Lett. 2010 Feb 1;20(3):1302-5. doi: 10.1016/j.bmcl.2009.10.018. Epub 2009 Oct 8.
2
Synthesis and antibacterial activity of dihydro-1,2-oxazine and 2-pyrazoline oxazolidinones: novel analogs of linezolid.二氢-1,2-恶嗪和2-吡唑啉恶唑烷酮的合成及其抗菌活性：利奈唑胺的新型类似物
Bioorg Med Chem Lett. 2005 Jun 2;15(11):2834-9. doi: 10.1016/j.bmcl.2005.03.099.
3
Synthesis and antibacterial activities of novel oxazolidinones having cyclic sulfonamide moieties.具有环状磺酰胺部分的新型恶唑烷酮的合成及其抗菌活性
Bioorg Med Chem Lett. 2008 Nov 1;18(21):5815-8. doi: 10.1016/j.bmcl.2008.09.034. Epub 2008 Sep 11.
4
Syntheses and biological studies of novel spiropiperazinyl oxazolidinone antibacterial agents using a spirocyclic diene derived acylnitroso Diels-Alder reaction.新型螺环哌嗪基恶唑烷酮类抗菌剂的合成及生物研究：利用螺环二烯衍生的酰基亚硝酰 Diels-Alder 反应。
Bioorg Med Chem. 2012 Jun 1;20(11):3422-8. doi: 10.1016/j.bmc.2012.04.026. Epub 2012 Apr 18.
5
Synthesis and antibacterial activity of 5-substituted oxazolidinones.5-取代噁唑烷酮类化合物的合成及其抗菌活性
Bioorg Med Chem. 2003 Jan 2;11(1):35-41. doi: 10.1016/s0968-0896(02)00423-6.
6
The synthesis and antibacterial activity of 1,3,4-thiadiazole phenyl oxazolidinone analogues.1,3,4-噻二唑苯基恶唑烷酮类似物的合成及其抗菌活性
Bioorg Med Chem Lett. 2003 Dec 1;13(23):4193-6. doi: 10.1016/j.bmcl.2003.07.018.
7
Effects of varied substituents on the antibacterial activity of triazolylmethyl oxazolidinones.取代基变化对三唑基甲基恶唑烷酮类化合物抗菌活性的影响。
Arch Pharm (Weinheim). 2012 Oct;345(10):790-803. doi: 10.1002/ardp.201100332. Epub 2012 Aug 8.
8
Synthesis and antibacterial activity of novel oxazolidinones bearing N-hydroxyacetamidine substituent.含N-羟基脒取代基的新型恶唑烷酮类化合物的合成与抗菌活性
Bioorg Med Chem Lett. 2006 May 1;16(9):2391-5. doi: 10.1016/j.bmcl.2006.01.109. Epub 2006 Feb 20.
9
Synthesis and antibacterial activity of a series of alpha-substituted acetylpiperazinyl oxazolidinones.一系列α-取代乙酰哌嗪基噁唑烷酮的合成及抗菌活性
Chem Biol Drug Des. 2009 Sep;74(3):276-81. doi: 10.1111/j.1747-0285.2009.00859.x.
10
Synthesis and antibacterial activities of N-substituted-glycinyl 1H-1,2,3-triazolyl oxazolidinones.N-取代甘氨酰 1H-1,2,3-三唑基噁唑烷酮的合成及抗菌活性。
Eur J Med Chem. 2013 Aug;66:246-57. doi: 10.1016/j.ejmech.2013.05.041. Epub 2013 Jun 7.
引用本文的文献
1
A Tandem Ring Closure and Nitrobenzene Reduction with Sulfide Provides an Improved Route to an Important Intermediate for the Anti-Tuberculosis Drug Candidate Sutezolid.硫化物介导的串联环化反应及硝基苯还原反应为抗结核候选药物舒替利福平的重要中间体提供了一条改进的合成路线。
Org Process Res Dev. 2024 Mar 27;28(4):1195-1204. doi: 10.1021/acs.oprd.4c00014. eCollection 2024 Apr 19.
2
Syntheses and biological studies of novel spiropiperazinyl oxazolidinone antibacterial agents using a spirocyclic diene derived acylnitroso Diels-Alder reaction.新型螺环哌嗪基恶唑烷酮类抗菌剂的合成及生物研究：利用螺环二烯衍生的酰基亚硝酰 Diels-Alder 反应。
Bioorg Med Chem. 2012 Jun 1;20(11):3422-8. doi: 10.1016/j.bmc.2012.04.026. Epub 2012 Apr 18.
3
Synthesis of unique scaffolds via Diels-Alder cycloadditions of tetrasubstituted cyclohexadienes.通过四取代环己二烯的 Diels-Alder 环加成反应合成独特的支架。
Org Lett. 2010 Apr 2;12(7):1592-5. doi: 10.1021/ol100318f.
本文引用的文献
1
New oxazolidinones.新型恶唑烷酮类化合物。
Curr Opin Microbiol. 2007 Oct;10(5):454-60. doi: 10.1016/j.mib.2007.08.001. Epub 2007 Oct 24.
2
Generation of acylnitroso dienophiles: a study of metal catalysis.酰基亚硝基亲双烯体的生成：金属催化研究
J Org Chem. 2007 Mar 30;72(7):2666-9. doi: 10.1021/jo062334y. Epub 2007 Feb 28.
3
Structure-antibacterial activity of arylcarbonyl- and arylsulfonyl-piperazine 5-triazolylmethyl oxazolidinones.芳基羰基和芳基磺酰基哌嗪5-三唑基甲基恶唑烷酮的结构-抗菌活性
Eur J Med Chem. 2007 Feb;42(2):214-25. doi: 10.1016/j.ejmech.2006.10.005. Epub 2006 Nov 29.
4
Antibacterial activity of pyrrolopyridine-substituted oxazolidinones: synthesis and in vitro SAR of various C-5 acetamide replacements.吡咯并吡啶取代噁唑烷酮类化合物的抗菌活性：各种C-5乙酰胺取代物的合成及体外构效关系
Bioorg Med Chem Lett. 2006 Sep 1;16(17):4537-42. doi: 10.1016/j.bmcl.2006.06.023. Epub 2006 Jun 27.
5
Synthesis and biological evaluation of purealin and analogues as cytoplasmic dynein heavy chain inhibitors.
J Med Chem. 2006 Mar 23;49(6):2063-76. doi: 10.1021/jm051030l.
6
Recent developments in the identification of novel oxazolidinone antibacterial agents.新型恶唑烷酮类抗菌剂鉴定的最新进展。
Bioorg Med Chem. 2006 Jun 15;14(12):4227-40. doi: 10.1016/j.bmc.2006.01.068. Epub 2006 Mar 9.
7
Rich chemistry of nitroso compounds.亚硝基化合物丰富的化学性质。
Chem Commun (Camb). 2005 Jul 28(28):3514-25. doi: 10.1039/b503212c. Epub 2005 Jun 24.
8
Synthesis and antibacterial activity of new N-linked 5-triazolylmethyl oxazolidinones.新型N-连接的5-三唑基甲基恶唑烷酮的合成与抗菌活性
Bioorg Med Chem. 2005 Jun 2;13(12):4113-23. doi: 10.1016/j.bmc.2005.03.036. Epub 2005 Apr 25.
9
AZD2563, a novel oxazolidinone: definition of antibacterial spectrum, assessment of bactericidal potential and the impact of miscellaneous factors on activity in vitro.新型恶唑烷酮类药物AZD2563：抗菌谱的界定、杀菌潜力评估以及多种因素对其体外活性的影响
Clin Microbiol Infect. 2004 Mar;10(3):247-54. doi: 10.1111/j.1198-743x.2004.00770.x.
10
Comparative in vitro activity of PH-027 versus linezolid and other anti-anaerobic antimicrobials against clinical isolates of Clostridium difficile and other anaerobic bacteria.PH-027与利奈唑胺及其他抗厌氧菌抗菌药物对艰难梭菌及其他厌氧菌临床分离株的体外活性比较
J Chemother. 2003 Apr;15(2):113-7. doi: 10.1179/joc.2003.15.2.113.
Zotero 插件