抗癌化合物 ZJ-101 的结构-活性关系研究：酰胺部分的作用。
Insights into the structure-activity relationship of the anticancer compound ZJ-101: A role played by the amide moiety.
机构信息
Department of Pharmaceutical Sciences and Experimental Therapeutics, College of Pharmacy, The University of Iowa, Iowa City, IA 52242, USA.
Department of Pharmacology and Molecular Sciences, Johns Hopkins University School of Medicine, 725 North Wolfe St., Baltimore, MD 21205, USA.
出版信息
Bioorg Med Chem Lett. 2024 Jun 1;105:129741. doi: 10.1016/j.bmcl.2024.129741. Epub 2024 Apr 9.
Abstract
ZJ-101, a structurally simplified analog of marine natural product superstolide A, was previously designed and synthesized in our laboratory. In the present study four new analogs of ZJ-101 were designed and synthesized to investigate the structure-activity relationship of the acetamide moiety of the molecule. The biological evaluation showed that the amide moiety is important for the molecule's anticancer activity. Replacing the amide with other functional groups such as a sulfonamide group, a carbamate group, and a urea group resulted in the decrease in anticancer activity.
摘要
ZJ-101 是海洋天然产物 superstitolide A 的结构简化类似物，之前由我们实验室设计和合成。在本研究中，设计并合成了 ZJ-101 的四个新类似物，以研究分子中酰胺部分的结构-活性关系。生物评价表明，酰胺部分对分子的抗癌活性很重要。用其他官能团（如磺酰胺基、氨基甲酸酯基和脲基）取代酰胺基会导致抗癌活性降低。
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2
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Int J Mol Sci. 2023 May 31;24(11):9575. doi: 10.3390/ijms24119575.
3
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Mar Drugs. 2022 Aug 18;20(8):528. doi: 10.3390/md20080528.
4
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Mar Drugs. 2019 Aug 23;17(9):491. doi: 10.3390/md17090491.
5
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Mar Drugs. 2019 Mar 8;17(3):163. doi: 10.3390/md17030163.
6
Marine Natural Products in Medicinal Chemistry.药物化学中的海洋天然产物
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