Synthesis, spectroscopic characterizations and cytotoxic activities of some novel 1,2-bis-(tetrasubstituted-benzylidene) hydrazine analogues

IF 1.3 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Bulletin of the Chemical Society of Ethiopia Pub Date : 2023-09-19 DOI:10.4314/bcse.v37i6.16

Ghaferah H. Al-Hazmi

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引用次数: 0

Abstract

ABSTRACT. The present work describes an efficient and convenient synthesis of a library of novel 1, 2-bis-(tetrasubstituted-benzylidene) hydrazine an analogue (3-7) 1,2-bis (3-methoxy-2-hydroxybenzlidene) hydrazine (3) and 1,2-bis (6-bromo-3-methoxy 2-hydroxybenzylidene) hydrazine (4), were obtained via opening of ester coumarin derivatives (1 and 2) with hydrazine hydrate under reflux. Diazotization of compound 4 with aryldiazonium chloride led to the formation of 1,2-bis (6-bromo-5-arylazo-3-methoxy-2-hydroxybenzylidene) hydrazine (6a,b). Acetylation of compounds 4 and 6a with acetic anhydride afforded the corresponding 1,2-bis (6-bromo-5-substituted-3-methoxy-2-acetoxy benzylidene) hydrazines (5 and 7). The cytotoxicity screening of some synthesized 1,2-bis (tetra substituted benzylidene) hydrazines (4-7) against breast cancer cell lines (MCF-7), and it was found several active compounds. Meanwhile compound 5 exhibited cytotoxic activity compared to reference drug. The DNA flow cytometry on MCF-7 cells of compound 5 was determined, it was found to cause G2/M phase arrest and induce apoptosis in all G1/M phases. In addition, compound 5 has been tested in other trials against aromatase inhibitors and tyrosinase inhibitors. KEY WORDS: Synthesis, Hydrazine derivatives, 1H NMR, Mass spectra, MCF-7 cell lines, Cytotoxicity Bull. Chem. Soc. Ethiop. 2023, 37(6), 1503-1520.DOI: https://dx.doi.org/10.4314/bcse.v37i6.16

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一些新型1,2-双(四取代苄基)肼类似物的合成、光谱表征和细胞毒活性

摘要本工作描述了一种高效方便的新型1,2-二(四取代-苄基)肼库的合成方法，类似物(3-7)1,2-二(3-甲氧基-2-羟基苄基)肼(3)和1,2-二(6-溴-3-甲氧基-2-羟基苄基)肼(4)是通过酯香豆素衍生物(1和2)与水合肼在回流下开孔得到的。化合物4与芳基氯重氮化反应生成1,2-二(6-溴-5-芳基偶氮-3-甲氧基-2-羟基苄基)肼(6a,b)。化合物4和6a与乙酸酐乙酰化得到相应的1,2-二(6-溴-5-取代-3-甲氧基-2-乙酰基苄基)肼(5和7)。对合成的1,2-二(四取代苄基)肼(4-7)对乳腺癌细胞株(MCF-7)进行了细胞毒性筛选，发现了一些活性化合物。与对照药物相比，化合物5表现出细胞毒活性。对化合物5的MCF-7细胞进行DNA流式细胞术检测，发现化合物5在G1/M期均可引起G2/M期阻滞并诱导凋亡。此外，化合物5已在其他试验中对芳香酶抑制剂和酪氨酸酶抑制剂进行了测试。关键词:合成，肼衍生物，1H NMR，质谱，MCF-7细胞系，细胞毒性;公牛。化学。Soc。中国生物医学工程学报，2016,37(6)，1503-1520。DOI: https://dx.doi.org/10.4314/bcse.v37i6.16

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来源期刊

Bulletin of the Chemical Society of Ethiopia 化学-化学综合

CiteScore

2.20

自引率

8.30%

发文量

113

审稿时长

6-12 weeks

期刊介绍： The Bulletin of the Chemical Society of Ethiopia (BCSE) is a triannual publication of the Chemical Society of Ethiopia. The BCSE is an open access and peer reviewed journal. The BCSE invites contributions in any field of basic and applied chemistry.