Discovery of Structural Diversity Guided N-S Heterocyclic Derivatives Based on Natural Benzothiazole Alkaloids as Potential Cytotoxic Agents

IF 2 3区化学 Q2 CHEMISTRY, ORGANIC

Journal of Heterocyclic Chemistry Pub Date : 2024-09-16 DOI:10.1002/jhet.4886

Lirong Guo, Yafei Wan, Manli Liu, Fuqiang Zheng, Yingwu Shi, Kaimei Wang, Xiufang Cao, Longzhu Bao, Shaoyong Ke

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Abstract

Benzothiazole alkaloids are a class of rare heterocyclic alkaloids with unique structures and exhibit a wide range of biological activities. So, the aim of this work is to investigate structural diversity-guided N-S heterocyclic derivatives based on natural benzothiazole alkaloids as potential cytotoxic agents. Three series of novel benzothiazole derivatives, including 22 compounds, were designed and synthesized using pharmacophore hybridization, and their in vitro cytotoxic activities against Huh-7 and A875 were fully evaluated. The results indicated that some of these benzothiazole derivatives had significantly good cytotoxic activities against two tested cell lines compared with the positive control 5-fluorouracil, and other compounds 3f–3i displayed good selectivity between A875 and Huh-7 cell lines, which might be used as promising lead molecule for discovery of novel benzothiazole-type cytotoxic agents.

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发现基于天然苯并噻唑生物碱的结构多样性引导的 N-S 杂环衍生物，作为潜在的细胞毒性药物

苯并噻唑生物碱是一类结构独特的稀有杂环生物碱，具有广泛的生物活性。因此，这项工作的目的是研究基于天然苯并噻唑生物碱的结构多样性引导的 N-S 杂环衍生物作为潜在的细胞毒剂。利用药代杂交技术设计并合成了三个系列的新型苯并噻唑衍生物，包括 22 个化合物，并全面评估了它们对 Huh-7 和 A875 的体外细胞毒性活性。结果表明，与阳性对照5-氟尿嘧啶相比，其中一些苯并噻唑衍生物对两种受试细胞株具有明显良好的细胞毒活性，其他化合物3f-3i在A875和Huh-7细胞株之间表现出良好的选择性，可作为发现新型苯并噻唑类细胞毒剂的先导分子。

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来源期刊

Journal of Heterocyclic Chemistry 化学-有机化学

CiteScore

5.20

自引率

4.20%

发文量

177

审稿时长

3.9 months

期刊介绍： The Journal of Heterocyclic Chemistry is interested in publishing research on all aspects of heterocyclic chemistry, especially development and application of efficient synthetic methodologies and strategies for the synthesis of various heterocyclic compounds. In addition, Journal of Heterocyclic Chemistry promotes research in other areas that contribute to heterocyclic synthesis/application, such as synthesis design, reaction techniques, flow chemistry and continuous processing, multiphase catalysis, green chemistry, catalyst immobilization and recycling.