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噻喃并[2,3 - ]噻唑作为药物化学中的新型高效骨架

Thiopyrano[2,3-]Thiazoles as New Efficient Scaffolds in Medicinal Chemistry.

作者信息

Kryshchyshyn Anna, Roman Olexandra, Lozynskyi Andrii, Lesyk Roman

机构信息

Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, Ukraine.

Department of General, Inorganic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, Ukraine.

出版信息

Sci Pharm. 2018 Jun 14;86(2):26. doi: 10.3390/scipharm86020026.

DOI:10.3390/scipharm86020026
PMID:29903979
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6027677/
Abstract

This review presents the up to date development of fused thiopyranothiazoles that comprise one of the thiazolidine derivatives classes. Thiazolidine and thiazolidinone-related compounds belong to the widely studied heterocycles from a medicinal chemistry perspective. From the chemical point of view, they are perfect heterodienes to undergo -Diels⁻Alder reaction with a variety of dienophiles, yielding regio- and diastereoselectively thiopyranothiazole scaffolds. The annealing of thiazole and thiopyran cycles in condensed heterosystem is a precondition for the “centers conservative” creation of the ligand-target binding complex and can promote a potential selectivity to biotargets. The review covers possible therapeutic applications of thiopyrano[2,3-]thiazoles, such as anti-inflammatory, antibacterial, anticancer as well as aniparasitic activities. Thus, thiopyrano[2,3-]thiazoles may be used as powerful tools in the development of biologically active agents and drug-like molecules.

摘要

本综述介绍了稠合噻吩并噻唑类化合物的最新进展,这类化合物属于噻唑烷衍生物类别之一。从药物化学角度来看,噻唑烷和噻唑烷酮相关化合物属于广泛研究的杂环化合物。从化学角度而言,它们是完美的杂二烯,可与多种亲双烯体发生狄尔斯-阿尔德反应,区域和非对映选择性地生成噻吩并噻唑骨架。在稠合杂环体系中噻唑环和噻吩并环的环合是“中心保守”创建配体-靶点结合复合物的前提条件,并且可以促进对生物靶点的潜在选择性。本综述涵盖了噻吩并[2,3-b]噻唑可能的治疗应用,如抗炎、抗菌、抗癌以及抗寄生虫活性。因此,噻吩并[2,3-b]噻唑可作为开发生物活性剂和类药物分子的有力工具。

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ACS Cent Sci. 2017 Mar 22;3(3):143-147. doi: 10.1021/acscentsci.7b00069. Epub 2017 Feb 28.
5
Feeling Nature's PAINS: Natural Products, Natural Product Drugs, and Pan Assay Interference Compounds (PAINS).感受大自然的“痛点”:天然产物、天然产物药物与泛分析干扰化合物(PAINS)
J Nat Prod. 2016 Mar 25;79(3):616-28. doi: 10.1021/acs.jnatprod.5b00947. Epub 2016 Feb 22.
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Synthesis and Anticancer Activity of New Thiopyrano[2,3-d]thiazoles Based on Cinnamic Acid Amides.基于肉桂酸酰胺的新型硫代吡喃并[2,3-d]噻唑的合成与抗癌活性
Sci Pharm. 2014 Sep 15;82(4):723-33. doi: 10.3797/scipharm.1408-05. Print 2014 Oct-Dec.
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Trends in research of antitrypanosomal agents among synthetic heterocycles.
Eur J Med Chem. 2014 Oct 6;85:51-64. doi: 10.1016/j.ejmech.2014.07.092. Epub 2014 Jul 25.
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4-Thiazolidinones: the advances continue….4-噻唑烷酮类:进展仍在继续……
Eur J Med Chem. 2014 Jan 24;72:52-77. doi: 10.1016/j.ejmech.2013.11.017. Epub 2013 Nov 27.
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Synthesis and Biological Activity of New Thiopyrano[2,3-d]thiazoles Containing a Naphthoquinone Moiety.含萘醌部分的新型硫代吡喃并[2,3 - d]噻唑的合成与生物活性
Sci Pharm. 2013 Apr-Jun;81(2):423-36. doi: 10.3797/scipharm.1301-13. Epub 2013 Feb 4.
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Facile construction of structurally diverse thiazolidinedione-derived compounds via divergent stereoselective cascade organocatalysis and their biological exploratory studies.通过发散性立体选择性级联有机催化构建结构多样的噻唑烷二酮衍生化合物及其生物探索性研究。
ACS Comb Sci. 2013 Jun 10;15(6):298-308. doi: 10.1021/co400022r. Epub 2013 May 8.