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3-1,2-二硫杂环戊烯-3-硫酮的合成与反应性。

Synthesis and Reactivity of 3-1,2-dithiole-3-thiones.

机构信息

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 119991 Moscow, Russia.

Nanotechnology Education and Research Center, South Ural State University, 454080 Chelyabinsk, Russia.

出版信息

Molecules. 2021 Jun 11;26(12):3595. doi: 10.3390/molecules26123595.

DOI:10.3390/molecules26123595
PMID:34208356
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8231234/
Abstract

3-1,2-Dithiole-3-thiones are among the best studied classes of polysulfur-containing heterocycles due to the almost explosive recent interest in these compounds as sources of hydrogen sulfide as an endogenously produced gaseous signaling molecule. This review covers the recent developments in the synthesis of these heterocycles, including both well-known procedures and important novel transformations for building the 1,2-dithiole-3-thione ring. Diverse ring transformations of 3-1,2-dithiole-3-thiones into various heterocyclic systems through 1,3-dipolar cycloaddition, replacement of one or two sulfur atoms to form carbon- and carbon-nitrogen containing moieties, and other unexpected reactions are considered.

摘要

3-1,2-二硫杂环戊烯-3-硫酮类化合物是含多硫杂环的化合物中研究最多的一类,这主要是因为最近人们对这些化合物作为内源性产生的气体信号分子硫化氢的来源产生了浓厚的兴趣。本文综述了这些杂环的最新合成进展,包括构建 1,2-二硫杂环戊烯-3-硫酮环的知名方法和重要的新型转化。通过 1,3-偶极环加成,3-1,2-二硫杂环戊烯-3-硫酮可以转化为各种杂环系统,通过取代一个或两个硫原子形成含碳和含碳-氮的部分,以及其他意想不到的反应也进行了考虑。

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IUCrdata. 2022 Oct 25;7(Pt 10):x221011. doi: 10.1107/S2414314622010112. eCollection 2022 Oct.
4
New Cycloadditon Reaction of 2-Chloroprop-2-enethioamides with Dialkyl Acetylenedicarboxylates: Synthesis of Dialkyl 2-[4,5-bis(alkoxycarbonyl)-2-(aryl{alkyl}imino)-3(2)-thienylidene]-1,3-dithiole-4,5-dicarboxylates.2-氯丙烯硫代酰胺与二烷基乙炔二羧酸酯的新型环加成反应:二烷基 2-[4,5-双(烷氧基羰基)-2-(芳基(烷基)亚氨基)-3(2)-噻吩基] -1,3-二硫杂环戊烯-4,5-二羧酸酯的合成。
Molecules. 2022 Oct 14;27(20):6887. doi: 10.3390/molecules27206887.
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Synthesis of Fluorinated and Fluoroalkylated Heterocycles Containing at Least One Sulfur Atom via Cycloaddition Reactions.通过环加成反应合成含至少一个硫原子的氟化和氟烷基化杂环化合物。
Materials (Basel). 2022 Oct 17;15(20):7244. doi: 10.3390/ma15207244.
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HS Donors and Their Use in Medicinal Chemistry.HS 供体及其在药物化学中的应用。
Biomolecules. 2021 Dec 18;11(12):1899. doi: 10.3390/biom11121899.
J Agric Food Chem. 2020 Feb 19;68(7):2214-2231. doi: 10.1021/acs.jafc.9b06360. Epub 2020 Feb 6.
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Copper-Catalyzed Tandem Sulfuration/Annulation of Propargylamines with Sulfur via C-N Bond Cleavage.铜催化通过 C-N 键断裂的炔丙胺与硫的串联硫化/环化反应。
J Org Chem. 2019 Jun 21;84(12):7894-7900. doi: 10.1021/acs.joc.9b00685. Epub 2019 Jun 7.
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Appendix A. dithioloquinolinethiones as new potential multitargeted antibacterial and antifungal agents: Synthesis, biological evaluation and molecular docking studies.附录 A. 二硫代氧杂喹啉硫酮类化合物作为新型潜在的多靶点抗菌和抗真菌药物:合成、生物评价和分子对接研究。
Eur J Med Chem. 2019 Aug 1;175:201-214. doi: 10.1016/j.ejmech.2019.04.046. Epub 2019 Apr 27.
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Switching Selectivity of α-Enolic Dithioesters: One Pot Access to Functionalized 1,2- and 1,3-Dithioles.α-烯醇式二硫代酯的选择性转换:一锅法制备功能化的 1,2-和 1,3-二硫杂环戊烯。
J Org Chem. 2016 Dec 2;81(23):11594-11602. doi: 10.1021/acs.joc.6b01802. Epub 2016 Nov 17.
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Synthesis and biological evaluation of novel hydrogen sulfide releasing nicotinic acid derivatives.新型硫化氢释放型烟酸衍生物的合成与生物学评价
Bioorg Med Chem. 2016 Nov 1;24(21):5368-5373. doi: 10.1016/j.bmc.2016.08.060. Epub 2016 Aug 30.
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4,5-Diaryl-3H-1,2-dithiole-3-thiones and related compounds as combretastatin A-4/oltipraz hybrids: Synthesis, molecular modelling and evaluation as antiproliferative agents and inhibitors of tubulin.4,5-二芳基-3H-1,2-二硫杂环戊烯-3-硫酮及相关化合物作为康普瑞他汀A-4/奥替普拉杂合物:合成、分子模拟以及作为抗增殖剂和微管蛋白抑制剂的评价
Eur J Med Chem. 2016 Oct 21;122:520-529. doi: 10.1016/j.ejmech.2016.06.055. Epub 2016 Jul 1.
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Synthesis of Amino-ADT Provides Access to Hydrolytically Stable Amide-Coupled Hydrogen Sulfide Releasing Drug Targets.氨基-ADT的合成提供了获得水解稳定的酰胺偶联硫化氢释放药物靶点的途径。
Synlett. 2016;27(9):1349-1353. doi: 10.1055/s-0035-1560603.
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Synthesis and biological evaluation of 1,2-dithiol-3-thiones and pyrrolo[1,2-a]pyrazines as novel hypoxia inducible factor-1 (HIF-1) inhibitor.新型缺氧诱导因子-1(HIF-1)抑制剂1,2-二硫醇-3-硫酮和吡咯并[1,2-a]吡嗪的合成及生物学评价
Bioorg Med Chem. 2016 Jun 15;24(12):2843-51. doi: 10.1016/j.bmc.2016.04.054. Epub 2016 Apr 26.