新型 3-亚甲基-1-磺酰基-2,3-二氢喹啉-4(1H)-酮的合成及抗癌活性。
Synthesis and Anticancer Properties of New 3-Methylidene-1-sulfonyl-2,3-dihydroquinolin-4(1)-ones.
机构信息
Institute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Lodz, Poland.
Department of Biomolecular Chemistry, Faculty of Medicine, Medicinal University of Lodz, Mazowiecka 6/8, 92-215 Lodz, Poland.
出版信息
Molecules. 2022 Jun 3;27(11):3597. doi: 10.3390/molecules27113597.
Quinolinones have been known for a long time as broad-spectrum synthetic antibiotics. More recently, the anticancer potential of this group of compounds has been investigated. Following this direction, we obtained a small library of 3-methylidene-1-sulfonyl-2,3-dihydroquinolin-4(1)-ones with various substituents at positions 1, 2, 6, and 7 of the quinolinone ring system. The cytotoxic activity of the synthesized analogs was tested in the MTT assay on two cancer cell lines in order to determine the structure-activity relationship. All compounds produced high cytotoxic effects in MCF-7, and even higher in HL-60 cells. 2-Ethyl-3-methylidene-1-phenylsulfonyl-2,3-dihydroquinolin-4(1)-one, which was over 5-fold more cytotoxic for HL-60 than for normal HUVEC cells, was selected for further tests. This analog was shown to inhibit proliferation and induce DNA damage and apoptosis in HL-60 cells.
喹啉酮类化合物作为广谱合成抗生素已经为人熟知。最近，人们研究了这组化合物的抗癌潜力。顺着这个方向，我们得到了一个小的 3-亚甲基-1-磺酰基-2,3-二氢喹啉-4(1)-酮库，其中喹啉酮环系统的 1、2、6 和 7 位具有不同的取代基。通过 MTT 测定法在两种癌细胞系上测试了合成类似物的细胞毒性活性，以确定构效关系。所有化合物在 MCF-7 中均产生了高细胞毒性作用，在 HL-60 细胞中甚至更高。2-乙基-3-亚甲基-1-苯基磺酰基-2,3-二氢喹啉-4(1)-酮对 HL-60 细胞的细胞毒性比正常 HUVEC 细胞高 5 倍以上，被选为进一步的测试。该类似物被证明可抑制 HL-60 细胞的增殖，并诱导其 DNA 损伤和凋亡。
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