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The enantioselective synthesis and biological evaluation of chimeric promysalin analogs facilitated by diverted total synthesis.

作者信息

Knouse Kyle W, Wuest William M

机构信息

Department of Chemistry, Temple University, Philadelphia, PA, USA.

出版信息

J Antibiot (Tokyo). 2016 Apr;69(4):337-9. doi: 10.1038/ja.2016.4. Epub 2016 Feb 10.

DOI:10.1038/ja.2016.4
PMID:26860469
Abstract
摘要

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The enantioselective synthesis and biological evaluation of chimeric promysalin analogs facilitated by diverted total synthesis.通过转向全合成实现嵌合普罗米萨林类似物的对映选择性合成及生物学评价。
J Antibiot (Tokyo). 2016 Apr;69(4):337-9. doi: 10.1038/ja.2016.4. Epub 2016 Feb 10.
2
Diverted Total Synthesis of Promysalin Analogs Demonstrates That an Iron-Binding Motif Is Responsible for Its Narrow-Spectrum Antibacterial Activity.经路线全合成普洛马林类似物证明,一个铁结合基序负责其窄谱抗菌活性。
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Total synthesis and biological investigation of (-)-promysalin.(-)-promysalin 的全合成及生物研究。
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Promysalin is a salicylate-containing antimicrobial with a cell-membrane-disrupting mechanism of action on Gram-positive bacteria.普罗米沙林是一种含水杨酸盐的抗菌药物,其作用机制是破坏革兰氏阳性菌的细胞膜。
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Rhodium catalysed conjugate addition of a chiral alkenyltrifluoroborate salt: the enantioselective synthesis of hermitamides A and B.铑催化手性链烯基三氟硼酸盐的共轭加成:隐士酰胺A和B的对映选择性合成。
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Promysalin Elicits Species-Selective Inhibition of Pseudomonas aeruginosa by Targeting Succinate Dehydrogenase.普罗米沙林通过靶向琥珀酸脱氢酶选择性抑制铜绿假单胞菌。
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Facile and diastereoselective synthesis of 3,2'-spiropyrrolidine-oxindoles derivatives, their molecular docking and antiproliferative activities.3,2'-螺吡咯烷-氧化吲哚衍生物的简便非对映选择性合成、分子对接及抗增殖活性
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1
Total synthesis and biological investigation of (-)-promysalin.(-)-promysalin 的全合成及生物研究。
J Am Chem Soc. 2015 Jun 17;137(23):7314-7. doi: 10.1021/jacs.5b04767. Epub 2015 Jun 5.
2
Carriebowlinol, an antimicrobial tetrahydroquinolinol from an assemblage of marine cyanobacteria containing a novel taxon.卡里鲍利诺,一种从含有新分类单元的海洋蓝细菌组合中提取的抗菌四氢喹啉醇。
J Nat Prod. 2015 Mar 27;78(3):534-8. doi: 10.1021/np500598x. Epub 2014 Dec 23.
3
Synthesis and evaluation of hermitamides A and B as human voltage-gated sodium channel blockers.
ACS Infect Dis. 2023 Dec 8;9(12):2386-2393. doi: 10.1021/acsinfecdis.3c00452. Epub 2023 Nov 8.
4
Target-Based Design of Promysalin Analogues Identifies a New Putative Binding Cleft in Succinate Dehydrogenase.基于靶点的促肌动蛋白类似物设计确定了琥珀酸脱氢酶中一个新的假定结合裂隙。
ACS Infect Dis. 2020 Jun 12;6(6):1372-1377. doi: 10.1021/acsinfecdis.0c00024. Epub 2020 Apr 14.
5
Recent Progress in Natural-Product-Inspired Programs Aimed To Address Antibiotic Resistance and Tolerance.天然产物启发的项目在解决抗生素耐药性和耐受性方面的最新进展。
J Med Chem. 2019 Sep 12;62(17):7618-7642. doi: 10.1021/acs.jmedchem.9b00370. Epub 2019 Apr 18.
6
Transcriptomic Profiling Suggests That Promysalin Alters the Metabolic Flux, Motility, and Iron Regulation in Pseudomonas putida KT2440.转录组分析表明,普罗米萨林改变了恶臭假单胞菌KT2440的代谢通量、运动性和铁调节。
ACS Infect Dis. 2018 Aug 10;4(8):1179-1187. doi: 10.1021/acsinfecdis.8b00041. Epub 2018 Jun 5.
7
Natural Products as Platforms To Overcome Antibiotic Resistance.作为克服抗生素耐药性平台的天然产物
Chem Rev. 2017 Oct 11;117(19):12415-12474. doi: 10.1021/acs.chemrev.7b00283. Epub 2017 Sep 27.
8
Decarboxylative alkenylation.脱羧烯基化反应
Nature. 2017 May 11;545(7653):213-218. doi: 10.1038/nature22307. Epub 2017 Apr 19.
9
Diverted Total Synthesis of Promysalin Analogs Demonstrates That an Iron-Binding Motif Is Responsible for Its Narrow-Spectrum Antibacterial Activity.经路线全合成普洛马林类似物证明,一个铁结合基序负责其窄谱抗菌活性。
J Am Chem Soc. 2016 May 11;138(18):5833-6. doi: 10.1021/jacs.6b03373. Epub 2016 Apr 28.
作为人类电压门控钠离子通道阻断剂的隐士酰胺 A 和 B 的合成与评价。
Bioorg Med Chem. 2011 Jul 15;19(14):4322-9. doi: 10.1016/j.bmc.2011.05.043. Epub 2011 May 30.
4
Diverted total synthesis leads to the generation of promising cell-migration inhibitors for treatment of tumor metastasis: in vivo and mechanistic studies on the migrastatin core ether analog.经路线转换的全合成导致产生有前途的细胞迁移抑制剂以治疗肿瘤转移:关于迁移他汀核心醚类似物的体内和机制研究。
J Am Chem Soc. 2010 Mar 10;132(9):3224-8. doi: 10.1021/ja9101503.
5
On the remarkable antitumor properties of fludelone: how we got there.论氟代酮的显著抗肿瘤特性:我们是如何做到的。
Angew Chem Int Ed Engl. 2005 May 6;44(19):2838-50. doi: 10.1002/anie.200461751.
6
An effective use of benzoic anhydride and its derivatives for the synthesis of carboxylic esters and lactones: a powerful and convenient mixed anhydride method promoted by basic catalysts.苯甲酸酐及其衍生物在羧酸酯和内酯合成中的有效应用:一种由碱性催化剂促进的强大且便捷的混合酸酐法。
J Org Chem. 2004 Mar 19;69(6):1822-30. doi: 10.1021/jo030367x.
7
Bis(((S)-binaphthoxy)(isopropoxy)titanium) oxide as a mu-oxo-type chiral Lewis acid: application to catalytic asymmetric allylation of aldehydes.双(((S)-联萘氧基)(异丙氧基)钛)氧化物作为一种μ-氧型手性路易斯酸:在醛的催化不对称烯丙基化反应中的应用
J Am Chem Soc. 2003 Feb 19;125(7):1708-9. doi: 10.1021/ja020338o.
8
Hermitamides A and B, toxic malyngamide-type natural products from the marine cyanobacterium Lyngbya majuscula.隐士酰胺A和B,来自海洋蓝藻巨大鞘丝藻的有毒马琳酰胺类天然产物。
J Nat Prod. 2000 Jul;63(7):952-5. doi: 10.1021/np000037x.