Synthesis of novel propargylated derivatives of noscapine using A3-coupling reaction and their anticancer properties

IF 2.2 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
Fatemeh Famarini, Peyman Salehi, Bahareh Heidari, Morteza Bararjanian, Atefeh Hajiagha Bozorgi, Afsaneh Tavasoli, Zahra Davarzani
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引用次数: 0

Abstract

A series of 21 novel compounds based on noscapine were synthesized and investigated as potential anticancer therapeutics. These new compounds were prepared from the N-demethylation of noscapine followed by the three-component A3-coupling of N-nornoscapine as a secondary amine, an aldehyde and a terminal alkyne catalyzed by copper iodide (CuI). Two classes of derivatives were synthesized by applying phenylacetylene and propargyl alcohol as the alkyne moiety. Chemical structures of the products were confirmed by 1HNMR, 13CNMR, and HR-MS. In vitro cytotoxicity of the synthesized derivatives was studied on MCF-7 breast cancer cell line treated with different doses of compounds for 48 h. Compounds 6l, 6n and 6h (IC50 = 18.94, 19.29 and 32.11 µM, respectively) displayed the highest potency compared to that of noscapine (IC50 = 36.38 µM).

利用 A3 偶联反应合成莨菪碱的新型丙炔基衍生物及其抗癌特性
我们合成了一系列 21 种基于莨菪碱的新型化合物,并将其作为潜在的抗癌疗法进行了研究。这些新化合物是通过碘化铜(CuI)催化 N-去甲莨菪碱作为仲胺、醛和末端炔的 N-去甲莨菪碱三组分 A3-偶联反应制备的。以苯基乙炔和丙炔醇作为炔基,合成了两类衍生物。通过 1HNMR、13CNMR 和 HR-MS 确认了产物的化学结构。化合物 6l、6n 和 6h(IC50 分别为 18.94、19.29 和 32.11 µM)与诺卡平(IC50 = 36.38 µM)相比显示出最高的效力。
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来源期刊
CiteScore
4.40
自引率
8.30%
发文量
230
审稿时长
5.6 months
期刊介绍: JICS is an international journal covering general fields of chemistry. JICS welcomes high quality original papers in English dealing with experimental, theoretical and applied research related to all branches of chemistry. These include the fields of analytical, inorganic, organic and physical chemistry as well as the chemical biology area. Review articles discussing specific areas of chemistry of current chemical or biological importance are also published. JICS ensures visibility of your research results to a worldwide audience in science. You are kindly invited to submit your manuscript to the Editor-in-Chief or Regional Editor. All contributions in the form of original papers or short communications will be peer reviewed and published free of charge after acceptance.
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