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饱和五元噻唑烷及其衍生物:从合成到生物应用。

Saturated Five-Membered Thiazolidines and Their Derivatives: From Synthesis to Biological Applications.

机构信息

Department of Chemistry, Synthetic Organic Chemistry Laboratory, MLSU, Udaipur, 313001, India.

Department of Pharmacy, B. N. University, MLSU, Udaipur, 313001, India.

出版信息

Top Curr Chem (Cham). 2020 Mar 23;378(2):34. doi: 10.1007/s41061-020-0298-4.

DOI:10.1007/s41061-020-0298-4
PMID:32206929
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7101601/
Abstract

In past decades, interdisciplinary research has been of great interest for scholars. Thiazolidine motifs behave as a bridge between organic synthesis and medicinal chemistry and compel researchers to explore new drug candidates. Thiazolidine motifs are very intriguing heterocyclic five-membered moieties present in diverse natural and bioactive compounds having sulfur at the first position and nitrogen at the third position. The presence of sulfur enhances their pharmacological properties, and, therefore, they are used as vehicles in the synthesis of valuable organic combinations. They show varied biological properties viz. anticancer, anticonvulsant, antimicrobial, anti-inflammatory, neuroprotective, antioxidant activity and so on. This diversity in the biological response makes it a highly prized moiety. Based on literature studies, various synthetic approaches like multicomponent reaction, click reaction, nano-catalysis and green chemistry have been employed to improve their selectivity, purity, product yield and pharmacokinetic activity. In this review article, we have summarized systematic approaches for the synthesis of thiazolidine and its derivatives, along with their pharmacological activity, including advantages of green synthesis, atom economy, cleaner reaction profile and catalyst recovery which will help scientists to probe and stimulate the study of these scaffolds.

摘要

在过去的几十年中,跨学科研究一直是学者们非常感兴趣的领域。噻唑烷类化合物作为有机合成和药物化学之间的桥梁,促使研究人员探索新的药物候选物。噻唑烷类化合物是非常有趣的五元杂环,存在于多种天然和生物活性化合物中,其特点是硫原子位于第一位,氮原子位于第三位。硫原子的存在增强了它们的药理特性,因此它们被用作合成有价值的有机化合物的载体。它们表现出多种生物活性,如抗癌、抗惊厥、抗菌、抗炎、神经保护、抗氧化活性等。这种生物反应的多样性使它成为一个非常有价值的部分。基于文献研究,已经采用了多种合成方法,如多组分反应、点击反应、纳米催化和绿色化学,以提高它们的选择性、纯度、产率和药代动力学活性。在这篇综述文章中,我们总结了噻唑烷及其衍生物的系统合成方法及其药理学活性,包括绿色合成、原子经济性、更清洁的反应谱和催化剂回收的优点,这将有助于科学家探索和激发对这些支架的研究。

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J Org Chem. 2025 Mar 28;90(12):4302-4312. doi: 10.1021/acs.joc.5c00020. Epub 2025 Mar 19.
5
Synthesis of cationic -acylated thiazolidine for selective activity against Gram-positive bacteria and evaluation of -acylation's role in membrane-disrupting activity.用于对革兰氏阳性菌具有选择性活性的阳离子酰化噻唑烷的合成及酰化在膜破坏活性中的作用评估。
RSC Med Chem. 2024 Oct 21. doi: 10.1039/d4md00626g.
6
Harnessing a bis-electrophilic boronic acid lynchpin for azaborolo thiazolidine (ABT) grafting in cyclic peptides.利用双亲电子硼酸关键分子在环肽中进行氮杂硼咯噻唑烷(ABT)接枝。
Chem Sci. 2024 Jul 30;15(34):13688-98. doi: 10.1039/d4sc04348k.
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Role of Ciminalum-4-thiazolidinone Hybrids in Molecular NF-κB Dependent Pathways.Ciminalum-4-噻唑烷酮杂合体在分子 NF-κB 依赖途径中的作用。
Int J Mol Sci. 2024 Jul 3;25(13):7329. doi: 10.3390/ijms25137329.
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Copper-Catalyzed One-Pot Synthesis of Thiazolidin-2-imines.铜催化一锅法合成噻唑烷-2-亚胺
J Org Chem. 2024 Jun 7;89(11):7727-7740. doi: 10.1021/acs.joc.4c00394. Epub 2024 May 9.
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Synthetic Strategies of Thiazolidine-2,4-dione Derivatives for the Development of New Anti-diabetic Agents: Compressive Review.噻唑烷-2,4-二酮衍生物的合成策略及其在新型抗糖尿病药物开发中的应用:综述。
Curr Top Med Chem. 2024;24(10):885-928. doi: 10.2174/0115680266284283240304071648.
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Synthesis of camphor thiazole derivates from and its bioactivity as antioxidants and antidiabetes against alpha glucosidase enzymes.由……合成樟脑噻唑衍生物及其作为抗氧化剂和抗α-葡萄糖苷酶的抗糖尿病生物活性。 (注:原文中“from and”表述有误,可能影响准确理解,这里按大致意思翻译)
MethodsX. 2023 Oct 10;11:102429. doi: 10.1016/j.mex.2023.102429. eCollection 2023 Dec.
新型 1,3-苯并二恶唑和 1,4-苯并二恶嗪的设计、合成与抗癌活性评价。
Eur J Pharm Sci. 2019 Nov 1;139:105045. doi: 10.1016/j.ejps.2019.105045. Epub 2019 Aug 14.
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Synthesis of new arylhydrazide bearing Schiff bases/thiazolidinone: α-Amylase, urease activities and their molecular docking studies.合成含席夫碱/噻唑烷酮的新型芳基酰肼:α-淀粉酶、脲酶活性及其分子对接研究。
Bioorg Chem. 2019 Oct;91:103112. doi: 10.1016/j.bioorg.2019.103112. Epub 2019 Jul 9.
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Cellulose matrix embedded copper decorated magnetic bionanocomposite as a green catalyst in the synthesis of dihydropyridines and polyhydroquinolines.纤维素基质嵌入铜修饰磁性生物纳米复合材料作为一种绿色催化剂在二氢吡啶和多氢喹啉的合成中的应用。
Carbohydr Polym. 2019 Mar 15;208:251-260. doi: 10.1016/j.carbpol.2018.12.069. Epub 2018 Dec 22.
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One-pot four-component synthesis of thiazolidin-2-imines using Cu/Zn dual catalysis: A new class of acetylcholinesterase inhibitors.一锅法四组分合成噻唑啉-2-亚胺:一类新型乙酰胆碱酯酶抑制剂。
Bioorg Chem. 2019 Mar;84:518-528. doi: 10.1016/j.bioorg.2018.12.002. Epub 2018 Dec 5.
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L-Proline functionalized magnetic nanoparticles: A novel magnetically reusable nanocatalyst for one-pot synthesis of 2,4,6-triarylpyridines.L-脯氨酸功能化磁性纳米粒子:一种新型的可磁回收纳米催化剂,用于一锅法合成 2,4,6-三芳基吡啶。
Sci Rep. 2018 Nov 23;8(1):17303. doi: 10.1038/s41598-018-35676-x.
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Synthesis, α-glucosidase inhibition and molecular docking studies of novel thiazolidine-2,4-dione or rhodanine derivatives.新型噻唑烷-2,4-二酮或罗丹宁衍生物的合成、α-葡萄糖苷酶抑制作用及分子对接研究
Medchemcomm. 2017 May 31;8(7):1477-1484. doi: 10.1039/c7md00173h. eCollection 2017 Jul 1.
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Synthesis of novel inhibitors of α-amylase based on the thiazolidine-4-one skeleton containing a pyrazole moiety and their configurational studies.基于含吡唑部分的噻唑烷-4-酮骨架的新型α-淀粉酶抑制剂的合成及其构型研究。
Medchemcomm. 2017 May 16;8(7):1468-1476. doi: 10.1039/c7md00080d. eCollection 2017 Jul 1.
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Ovicidal in vitro activity of 2-aryl-3-(2-morpholinoethyl)thiazolidin-4-ones and 2-aryl-3-(3-morpholinopropyl)thiazolidin-4-ones against Fasciola hepatica (Linnaeus, 1758).2-芳基-3-(2-吗啉代乙基)噻唑烷-4-酮和2-芳基-3-(3-吗啉代丙基)噻唑烷-4-酮对肝片吸虫(Linnaeus,1758)的体外杀卵活性
Exp Parasitol. 2018 Sep;192:60-64. doi: 10.1016/j.exppara.2018.07.012. Epub 2018 Jul 21.