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首页> 外文期刊>ACS combinatorial science >Facile Construction of Structurally Diverse Thiazolidinedione-Derived Compounds via Divergent Stereoselective Cascade Organocatalysis and Their Biological Exploratory Studies
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Facile Construction of Structurally Diverse Thiazolidinedione-Derived Compounds via Divergent Stereoselective Cascade Organocatalysis and Their Biological Exploratory Studies

机译：通过不同的立体选择性级联有机催化轻松构建结构多样的噻唑烷二酮衍生化合物及其生物学探索性研究

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In this article, we present a new approach by merging two powerful synthetic tactics, divergent synthesis and cascade organocatalysis, to create a divergent cascade organocatalysis strategy for the facile construction of new "privileged" substructure-based DOS (pDOS) library. As demonstrated, notably 5 distinct molecular architectures are produced facilely from readily available simple synthons thiazolidinedione and its analogues and α,β-unsaturated aldehydes in 1—3 steps with the powerful strategy. The beauty of the chemistry is highlighted by the efficient formation of structurally new and diverse products from structurally close reactants under the similar reaction conditions. Notably, structurally diverse spiro-thiazolidmediones and -rhodanines are produced from organocatalytic enantioselective 3-component Michael—Michael—aldol cascade reactions of respective thiazolidinediones and rhodanines with enals. Nevertheless, under the similar reaction conditions, reactions" of isorhodanine via a Michael—cyclization cascade lead to structurally different fused thiopyranoid scaffolds. This strategy sigruficantly minimizes time- and cost-consuming synthetic works. Furthermore, these molecules possess high structural complexity and functional, stereochemical, and skeletal diversity with similarity to natural scaffolds. In the preliminary biological studies of these molecules, compounds 4f, 8a, and 10a exhibit inhibitory activity against the human breast cancer cells, while compunds 8a, 9a, and 9b display good antifungal activities against Candida albicans and Cryptococcus neoformans. Notably, their structures are different from clinically used triazole antifungal drugs. Therefore, they could serve as good lead compounds for the development of new generation of antifungal agents.
机译：在本文中，我们通过合并两种强大的合成策略（发散性合成和级联有机催化）提出了一种新方法，以创建易于级联的新的基于子结构的基于DOS的DOS（pDOS）库的发散级联有机催化策略。如所证明的，通过强大的策略，可以容易地从简单易得的简单合成子噻唑烷二酮及其类似物和α，β-不饱和醛中轻松生成5种不同的分子结构。在相似的反应条件下，由结构紧密的反应物有效形成结构多样的新产品，突出了化学的美。值得注意的是，结构上不同的螺-噻唑烷二酮和-罗丹宁是由各自的噻唑烷二酮和罗丹酮与烯醛的有机催化对映选择性3-组分Michael-Michael-aldol级联反应产生的。然而，在相似的反应条件下，异黄酮通过迈克尔-环化级联反应导致结构上不同的稠合噻吩并吡喃类支架。这种策略极大地减少了耗时和成本的合成工作。此外，这些分子具有很高的结构复杂性和功能性，立体化学和骨骼多样性与天然支架相似，在对这些分子的初步生物学研究中，化合物4f，8a和10a表现出对人乳腺癌细胞的抑制活性，而化合物8a，9a和9b表现出对人乳腺癌的良好抗真菌活性。白色念珠菌和新隐球菌的结构与临床使用的三唑类抗真菌药不同，因此可以作为开发新一代抗真菌剂的良好先导化合物。

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