吲哚与重氮盐的 C-2 芳基化反应：2,3-二取代吲哚的合成及其抗菌活性。
Unprecedented C-2 arylation of indole with diazonium salts: Syntheses of 2,3-disubstituted indoles and their antimicrobial activity.
机构信息
Department of Biology, New Mexico Institute of Mining and Technology, Socorro, NM 87801, USA.
出版信息
Bioorg Med Chem Lett. 2011 Aug 15;21(16):4720-3. doi: 10.1016/j.bmcl.2011.06.081. Epub 2011 Jun 25.
Abstract
A novel reaction of indole with aryldiazonium salts leading to the formation of 2-aryl-3-(arylazo)indoles was discovered. The products were found to possess potent anti-MRSA and anti-LLVRE activities. The SAR studies indicate that the potentially metabolically labile azo functionality can be replaced with ether oxygen and thioether sulfur atoms without any loss of activity.
摘要
发现了吲哚与芳基重氮盐的新型反应，生成了 2-芳基-3-(芳偶氮基)吲哚。发现这些产物具有很强的抗耐甲氧西林金黄色葡萄球菌（MRSA）和抗利奈唑胺肠球菌（LLVRE）活性。SAR 研究表明，潜在的代谢不稳定的偶氮官能团可以被醚氧和硫醚硫原子取代，而不会损失任何活性。
相似文献
1
Unprecedented C-2 arylation of indole with diazonium salts: Syntheses of 2,3-disubstituted indoles and their antimicrobial activity.吲哚与重氮盐的 C-2 芳基化反应：2,3-二取代吲哚的合成及其抗菌活性。
Bioorg Med Chem Lett. 2011 Aug 15;21(16):4720-3. doi: 10.1016/j.bmcl.2011.06.081. Epub 2011 Jun 25.
2
Antimicrobial study of newly synthesized 6-substituted indolo[1,2-c]quinazolines.新合成的 6-取代吲哚并[1,2-c]喹唑啉的抗菌研究。
Eur J Med Chem. 2010 Mar;45(3):1200-5. doi: 10.1016/j.ejmech.2009.11.038. Epub 2009 Nov 26.
3
The acid-catalysed synthesis of 7-azaindoles from 3-alkynyl-2-aminopyridines and their antimicrobial activity.酸催化 3-炔基-2-氨基吡啶合成 7-氮茚并化合物及其抗菌活性。
Org Biomol Chem. 2014 Jan 14;12(2):307-15. doi: 10.1039/c3ob41798k.
4
Phenylazoindole dyes--part I: the syntheses, characterizations, crystal structures, quantum chemical calculations and antimicrobial properties.偶氮苯并吲哚染料——第一部分：合成、表征、晶体结构、量子化学计算和抗菌性能。
Spectrochim Acta A Mol Biomol Spectrosc. 2013 Sep;113:314-24. doi: 10.1016/j.saa.2013.04.081. Epub 2013 May 14.
5
Novel indole-thiazolidinone conjugates: Design, synthesis and whole-cell phenotypic evaluation as a novel class of antimicrobial agents.新型吲哚噻唑烷酮化合物的设计、合成及全细胞表型评价：一类新型抗菌药物。
Eur J Med Chem. 2018 Dec 5;160:49-60. doi: 10.1016/j.ejmech.2018.10.008. Epub 2018 Oct 4.
6
Design and synthesis of spiro[indole-thiazolidine]spiro[indole-pyrans] as antimicrobial agents.设计和合成螺[吲哚-噻唑烷]螺[吲哚-吡喃]作为抗菌剂。
Bioorg Med Chem Lett. 2011 Sep 15;21(18):5465-9. doi: 10.1016/j.bmcl.2011.06.121. Epub 2011 Jul 2.
7
The synthesis of 2- and 3-aryl indoles and 1,3,4,5-tetrahydropyrano[4,3-b]indoles and their antibacterial and antifungal activity.2-和3-芳基吲哚以及1,3,4,5-四氢吡喃并[4,3-b]吲哚的合成及其抗菌和抗真菌活性。
Bioorg Med Chem Lett. 2009 Sep 1;19(17):4948-51. doi: 10.1016/j.bmcl.2009.07.091. Epub 2009 Jul 22.
8
Synthesis and biological evaluation of novel N-acyl substituted quinolin-2(1H)-one derivatives as potential antimicrobial agents.新型 N-酰基取代喹啉-2(1H)-酮衍生物的合成与生物评价作为潜在的抗菌剂。
Bioorg Med Chem Lett. 2012 Sep 15;22(18):5845-8. doi: 10.1016/j.bmcl.2012.07.081. Epub 2012 Aug 1.
9
Recent Developments in the Synthesis and Antimicrobial Activity of Indole and its Derivatives.吲哚及其衍生物的合成与抗菌活性的最新进展
Curr Org Synth. 2019;16(1):17-37. doi: 10.2174/1570179415666181113144939.
10
Synthesis of a new class of antimicrobial agents incorporating the indolin-2-one moiety.合成具有吲唑-2-酮部分的新型抗菌剂。
J Enzyme Inhib Med Chem. 2013 Aug;28(4):853-62. doi: 10.3109/14756366.2012.689298. Epub 2012 May 31.
引用本文的文献
1
Water Effect on the Photochemistry of Arylazo Sulfonates.水对芳基偶氮磺酸盐光化学的影响。
J Org Chem. 2025 May 23;90(20):6726-6736. doi: 10.1021/acs.joc.5c00314. Epub 2025 Apr 30.
2
Synthesis of Indolyl Phenyl Diketones through Visible-Light-Promoted Ni-Catalyzed Intramolecular Cyclization/Oxidation Sequence of Ynones.通过可见光促进的炔酮的镍催化分子内环化/氧化序列合成吲哚基苯基二酮
ACS Org Inorg Au. 2023 Dec 21;4(2):241-247. doi: 10.1021/acsorginorgau.3c00060. eCollection 2024 Apr 3.
3
Synergistic action of substituted indole derivatives and clinically used antibiotics against drug-resistant bacteria.取代吲哚衍生物与临床使用抗生素对耐药菌的协同作用。
Future Microbiol. 2020 May;15(8):579-590. doi: 10.2217/fmb-2019-0094. Epub 2020 Jun 2.
4
Photo-physical properties of substituted 2,3-distyryl indoles: Spectroscopic, computational and biological insights.取代的2,3-二苯乙烯基吲哚的光物理性质：光谱、计算和生物学见解。
J Photochem Photobiol A Chem. 2019 May 1;376:73-79. doi: 10.1016/j.jphotochem.2019.03.005. Epub 2019 Mar 6.
5
Photoactivated 2,3-distyrylindoles kill multi-drug resistant bacteria.光活化 2,3-二取代吲哚杀死多药耐药菌。
Bioorg Med Chem Lett. 2018 Jun 1;28(10):1879-1886. doi: 10.1016/j.bmcl.2018.04.001. Epub 2018 Apr 3.
6
Dual vicinal functionalisation of heterocycles an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade.杂环的双邻位官能化——一种中断的普默勒尔偶联/[3,3] - 西格玛重排串联反应
Chem Sci. 2017 Nov 17;9(3):754-759. doi: 10.1039/c7sc04723a. eCollection 2018 Jan 21.
7
Spectroscopic Study of a Photoactive Antibacterial Agent: 2,3-Distyrylindole.一种光活性抗菌剂：2,3-二苯乙烯基吲哚的光谱研究
J Phys Chem A. 2018 Feb 1;122(4):937-945. doi: 10.1021/acs.jpca.7b09638. Epub 2018 Jan 23.
8
Mild and selective base-free C-H arylation of heteroarenes: experiment and computation.杂芳烃的温和且选择性无碱C-H芳基化：实验与计算
Chem Sci. 2017 Feb 1;8(2):1046-1055. doi: 10.1039/c6sc02595a. Epub 2016 Sep 5.
9
Exploration of C-H and N-H-bond functionalization towards 1-(1,2-diarylindol-3-yl)tetrahydroisoquinolines.探索 1-(1,2-二芳基吲哚-3-基)四氢异喹啉中 C-H 和 N-H 键的功能化。
Beilstein J Org Chem. 2014 Sep 15;10:2186-99. doi: 10.3762/bjoc.10.226. eCollection 2014.
10
Chiral anion phase transfer of aryldiazonium cations: an enantioselective synthesis of C3-diazenated pyrroloindolines.芳基重氮阳离子的手性阴离子相转移：C3-重氮基吡咯并吲哚啉的对映选择性合成
Angew Chem Int Ed Engl. 2014 May 26;53(22):5600-3. doi: 10.1002/anie.201310905. Epub 2014 Apr 8.
本文引用的文献
1
Structural simplification of bioactive natural products with multicomponent synthesis. 3. Fused uracil-containing heterocycles as novel topoisomerase-targeting agents.生物活性天然产物的多组分合成结构简化。3. 含融合尿嘧啶杂环作为新型拓扑异构酶靶向剂。
J Med Chem. 2011 Apr 14;54(7):2012-21. doi: 10.1021/jm1009428. Epub 2011 Mar 9.
2
Invasive community-associated MRSA infections: epidemiology and antimicrobial management.社区相关性耐甲氧西林金黄色葡萄球菌感染的侵袭性疾病：流行病学和抗菌药物管理。
Expert Opin Pharmacother. 2010 Dec;11(18):3009-25. doi: 10.1517/14656566.2010.511614. Epub 2010 Oct 19.
3
Bottromycin derivatives: efficient chemical modifications of the ester moiety and evaluation of anti-MRSA and anti-VRE activities.博替霉素衍生物：酯基的有效化学修饰及抗耐甲氧西林金黄色葡萄球菌和抗万古霉素肠球菌活性的评价。
Bioorg Med Chem Lett. 2010 Oct 15;20(20):6116-20. doi: 10.1016/j.bmcl.2010.08.037. Epub 2010 Aug 18.
4
Design, synthesis, and biological evaluation of a novel series of quercetin diacylglucosides as potent anti-MRSA and anti-VRE agents.新型槲皮素二酰基葡萄糖苷类化合物的设计、合成及抗 MRSA 和抗 VRE 活性评价。
Bioorg Med Chem Lett. 2010 Sep 1;20(17):5349-52. doi: 10.1016/j.bmcl.2010.02.060. Epub 2010 Feb 19.
5
Synthesis and structure-activity relationship of dicationic diaryl ethers as novel potent anti-MRSA and anti-VRE agents.新型强效抗耐甲氧西林金黄色葡萄球菌和抗耐万古霉素肠球菌药物——双阳离子二芳基醚的合成及其构效关系
Bioorg Med Chem Lett. 2009 Aug 15;19(16):4626-9. doi: 10.1016/j.bmcl.2009.06.077. Epub 2009 Jun 25.
6
Inhibitory and resistance-modifying potential of plant-based alkaloids against methicillin-resistant Staphylococcus aureus (MRSA).
Curr Microbiol. 2009 Aug;59(2):181-6. doi: 10.1007/s00284-009-9416-9. Epub 2009 May 28.
7
Vancomycin-resistant enterococci (VRE): transmission and control.耐万古霉素肠球菌（VRE）：传播与控制
Int J Antimicrob Agents. 2008 Feb;31(2):99-106. doi: 10.1016/j.ijantimicag.2007.08.026. Epub 2007 Dec 31.
8
Synthesis of novel azo Schiff bases and their antibacterial and antifungal activities.新型偶氮席夫碱的合成及其抗菌和抗真菌活性。
Molecules. 2004 Sep 30;9(10):815-24. doi: 10.3390/91000815.
9
A practical synthesis of alpha-aryl methyl ketones via a transition-metal-free Meerwein arylation.通过无过渡金属的Meerwein芳基化反应实现α-芳基甲基酮的实用合成。
J Org Chem. 2007 Mar 2;72(5):1856-8. doi: 10.1021/jo062483g. Epub 2007 Jan 31.
10
New arylthioindoles: potent inhibitors of tubulin polymerization. 2. Structure-activity relationships and molecular modeling studies.新型芳硫基吲哚：微管蛋白聚合的强效抑制剂。2. 构效关系与分子模拟研究。
J Med Chem. 2006 Feb 9;49(3):947-54. doi: 10.1021/jm050809s.
Zotero 插件