Tetra-azolium Salts Induce Significant Cytotoxicity in Human Colon Cancer Cells In vitro.

IF 1.7 4区化学 Q3 CHEMISTRY, ORGANIC Current organic synthesis Pub Date : 2024-01-01 DOI:10.2174/1570179421666230824151219

Muhammad Ashraf, Amna Kamal, Ejaz Ahmed, Haq Nawaz Bhatti, Muhammad Arshad, Muhammad Adnan Iqbal

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Abstract

Background: Azolium salts are the organic salts used as stable precursors for generating N-Heterocyclic Carbenes and their metal complexes. Azolium salts have also been reported to have significant biological potential. Hence, in the current study, four tetra-dentate azolium salts were derived from bis-azolium salts by a new synthetic strategy.

Methods: The tetra azolium salts have been synthesized by reacting the imidazole or methyl imidazole with dibromo xylene (meta, para)/ 1-bromo methyl imidazole or dibromo ethane resulting in the mono or bis azolium salts namely I-IV. V-VII have been obtained by reacting I with II-IV, resulting in the tetra azolium salts. Each product was analyzed by various analytical techniques, i.e., microanalysis, FT-IR, and NMR (1H & 13C). Salts V-VII were evaluated for their antiproliferative effect against human colon cancer cells (HCT-116) using MTT assay.

Results: Four chemical shifts for acidic protons between 8.5-9.5 δ ppm in 1H NMR and resonance of respective carbons around 136-146 δ ppm in 13C NMR indicated the successful synthesis of tetra azolium salts. Salt V showed the highest IC50 value, 24.8 μM among all synthesized compounds.

Conclusion: Tetra-azolium salts may play a better cytotoxicity effect compared to mono-, bi-& tri-azolium salts.

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四唑盐在体外诱导人类结肠癌细胞产生显著的细胞毒性。

背景：唑盐是用作生成 N-杂环烯及其金属络合物的稳定前体的有机盐。据报道，唑盐还具有重要的生物潜力。因此，本研究采用一种新的合成策略，从双唑盐中得到了四种四齿唑盐：方法：通过将咪唑或甲基咪唑与二溴二甲苯（元、对位）/1-溴甲基咪唑或二溴乙烷反应，合成出单或双唑盐，即 I-IV。V-VII 是通过 I 与 II-IV 反应得到的四唑盐。每种产品都通过各种分析技术进行了分析，如显微分析、傅立叶变换红外光谱和核磁共振（1H 和 13C）。使用 MTT 法评估了盐 V-VII 对人结肠癌细胞（HCT-116）的抗增殖作用：结果：1H NMR 中酸性质子的四个化学位移在 8.5-9.5 δ ppm 之间，13C NMR 中各碳的共振在 136-146 δ ppm 左右，这表明四唑盐的成功合成。在所有合成的化合物中，盐 V 的 IC50 值最高，为 24.8 μM：结论：与单唑盐、双唑盐和三唑盐相比，四唑盐可能具有更好的细胞毒性作用。

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来源期刊

Current organic synthesis 化学-有机化学

CiteScore

3.40

自引率

5.60%

发文量

审稿时长

6-12 weeks

期刊介绍： Current Organic Synthesis publishes in-depth reviews, original research articles and letter/short communications on all areas of synthetic organic chemistry i.e. asymmetric synthesis, organometallic chemistry, novel synthetic approaches to complex organic molecules, carbohydrates, polymers, protein chemistry, DNA chemistry, supramolecular chemistry, molecular recognition and new synthetic methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by experts who are internationally known for their eminent research contributions. The journal is essential reading to all synthetic organic chemists. Current Organic Synthesis should prove to be of great interest to synthetic chemists in academia and industry who wish to keep abreast with recent developments in key fields of organic synthesis.