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通过席夫碱和偶氮键连接的新型异恶唑环的分子建模、合成及抗增殖评估

Molecular modeling, synthesis, and antiproliferative evaluation of new isoxazole ring linked by Schiff bases and azo bond.

作者信息

Taha Duha E, Mahdi Monther F, Raauf Ayad M R

机构信息

Department of Pharmaceutical Chemistry, College of Pharmacy, Mustansiriyah University, Baghdad, Iraq.

College of Pharmacy, Al-Farahidi University, Baghdad, Iraq.

出版信息

J Adv Pharm Technol Res. 2023 Jul-Sep;14(3):213-219. doi: 10.4103/japtr.japtr_170_23. Epub 2023 Jul 28.

DOI:10.4103/japtr.japtr_170_23
PMID:37692009
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10483917/
Abstract

Lung cancer is the most common malignancy worldwide, with approximately 1.8 million new cases yearly. Cytotoxic drugs are frequently used in cancer treatment. Even though the medicine enhances patients' quality of life, several drawbacks diminish its efficacy. Drug resistance and many disadvantages associated with chemotherapeutic drug side effects continue to be significant factors limiting the efficiency of cancer treatment. This necessitates developing new effective strategies that target tumors with minimal adverse effects. This research aims to overcome these issues by synthesizing a new series of compounds with an isoxazole ring attached by Schiff bases and azo bonds based on molecular docking with the (Genetic Optimization of Ligand Docking) program and estimating the pharmacokinetic properties with the Swiss ADME. The greatest-fitting compounds were then manufactured and verified by spectral analysis (FT-IR, H NMR, and C NMR), MTT assay for assessment of antiproliferative activities against A549 lung cancer cell lines showed that compounds 5a and 5b had an inhibitory concentration half-maximal inhibitory concentration (IC) (17.34 and 18.32 μM), respectively, which was significantly lower than the inhibitory concentration of erlotinib (IC = 25.06 μM).

摘要

肺癌是全球最常见的恶性肿瘤，每年约有180万新发病例。细胞毒性药物常用于癌症治疗。尽管这种药物提高了患者的生活质量，但一些缺点降低了其疗效。耐药性以及与化疗药物副作用相关的许多不利因素仍然是限制癌症治疗效率的重要因素。这就需要开发新的有效策略，以最小的副作用靶向肿瘤。本研究旨在通过基于（配体对接的遗传优化）程序进行分子对接，合成一系列通过席夫碱和偶氮键连接异恶唑环的新化合物，并使用瑞士ADME评估其药代动力学性质，以克服这些问题。然后制备最适合的化合物，并通过光谱分析（傅里叶变换红外光谱、氢核磁共振和碳核磁共振）进行验证，针对A549肺癌细胞系的MTT法抗增殖活性评估表明，化合物5a和5b的半数抑制浓度（IC）分别为17.34和18.32 μM，显著低于厄洛替尼的抑制浓度（IC = 25.06 μM）。

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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d511/10483917/47d5f71491fb/JAPTR-14-213-g008.jpg
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