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Design, Synthesis, and Spectroscopic Studies of Some New α-Aminophosphonate Analogues Derived from 4-Hydroxybenzaldehyde with Special Reference to Anticancer Activity
Drug Design, Development and Therapy ( IF 4.8 ) Pub Date : 2022-08-05 , DOI: 10.2147/dddt.s357998
Omar M Ali 1 , Mohammed T Alotaibi 1 , Yasser H Zaki 2 , Hamada H Amer 3
Affiliation  

Introduction: As biological activity components, α-aminophosphonates and their moieties play important roles in medicinal chemistry. Alpha-phosphonic acids are significant α-amino acid counterparts. Due to its strong biological activity, this class of molecule has recently been discovered to have numerous medical applications.
Results and Discussion: A new class of α-aminophosphonates and arylidene derivatives was synthesized. Various spectroscopic and elemental analyses were used to confirm the prepared products. The produced materials were tested as anticancer against breast carcinoma cells and normal human cells (PBMC). Besides the analysis results, it was found that ( 7b, 4c, 5k, 6, 5a, 7c, 5f, 5b, and 5g) against MCF-7 line cells. As a reference anticancer drug, 5-fluorouracil was used. The anticancer activities showed that the compounds 7b, 4c, containing α-aminophosphonate and Schiff base groups, respectively, showed high inhibition activity against the MCF-7 cell line, with 94.32% and 92.45% inhibition compared to the inhibition by 5-FU with 96.02% inhibition. The results showed that the compounds 5k, 7b, 6, and 5a, respectively, had very low activity against normal human cells PBMC, with 12.77%, 13%, 13.13%, and 17.88% inhibition compared to the inhibition by 5-FU with 12.50% inhibition. The binding energy for non-bonding interactions between the ligand (studied compounds) and receptor, thymidylate synthase, was determined using molecular docking (pdb code: 1AN5).
Conclusion: α-aminophosphonate derivatives, arylidines, and disphosphonate derivatives derived from 4-hydroxybenzaldehyde were synthesized, purified, elucidated by spectroscopic analysis, and finally tested against carcinoma breast cancer to give high to moderate to low activity.
Graphical Abstract:

Keywords: synthesis, phosphonates, arylidene derivatives, 4-hydroxybenzaldehyde, anticancer activity


中文翻译:

一些衍生自 4-羟基苯甲醛的新型 α-氨基膦酸盐类似物的设计、合成和光谱研究,特别涉及抗癌活性

简介:作为生物活性成分,α-氨基膦酸盐及其部分在药物化学中发挥着重要作用。α-膦酸是重要的α-氨基酸对应物。由于其强大的生物活性,最近发现这类分子具有许多医学应用。
结果与讨论:合成了一类新的α-氨基膦酸盐和亚芳基衍生物。各种光谱和元素分析用于确认制备的产品。所生产的材料被测试为抗乳腺癌细胞和正常人类细胞 (PBMC) 的抗癌剂。除分析结果外,还发现(7b、4c、5k、6、5a、7c、5f、5b5g) 针对 MCF-7 系细胞。作为参考抗癌药物,使用5-氟尿嘧啶。抗癌活性表明,含有α-氨基膦酸盐和席夫碱基团的化合物7b、4c分别对MCF-7细胞系显示出较高的抑制活性,与5-FU的抑制作用相比,抑制作用分别为94.32%和92.45%。 96.02% 抑制。结果表明,化合物5k、7b、65a分别对正常人细胞 PBMC 具有非常低的活性,与 5-FU 抑制 12.50% 相比,抑制 12.77%、13%、13.13% 和 17.88%。使用分子对接(pdb 代码:1AN5)确定配体(研究的化合物)和受体胸苷酸合酶之间的非键合相互作用的结合能。
结论:合成、纯化4-羟基苯甲醛衍生的α-氨基膦酸盐衍生物、芳烷基和二膦酸盐衍生物,经光谱分析阐明,最终对乳腺癌进行了高、中、低活性测试。
图解摘要:

关键词:合成,膦酸盐,亚芳基衍生物,4-羟基苯甲醛,抗癌活性
更新日期:2022-08-05
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