Design, synthesis of novel substituted imidazole derivatives: Cytotoxicity and molecular docking studies

IF 2.218 Q2 Chemistry

Chemical Data Collections Pub Date : 2023-10-01 DOI:10.1016/j.cdc.2023.101061

Prasad Chennamsetti , Kishan Chevula , Nagesh Patnam , Vishnu Thumma , Vijjulatha Manga

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Abstract

A novel series of 5-(2-chlorophenyl)-4-(3,4-dimethoxyphenyl)-2-(substituted phenyl)-1H-imidazole derivatives 3(a-m) were synthesized by one pot synthesis of diketone, aldehyde and ammonium acetate. The structures of novel compounds were established by interpretation of IR, ¹H NMR, ¹³C NMR and Mass spectral data. Evaluated their invitro anticancer activity against human cervical cancer HeLa cell line by MTT assay using Cisplatin as standard reference drug. Compounds 3e (R₃ = 4-cyanophenoxy), 3c (R₃ = 2-nitrophenoxy) and 3 g (R₂ = 4-nitrophenoxy & R₃ = methoxy) exhibited outstanding activity against the HeLa cell line with IC₅₀ value of 2.7 ± 0.4351 μM, 4.824 ± 0.8869 μM and 6.877 ± 0.6042 μM respectively, compared to Cisplatin IC₅₀ value of 7.06 ± 0.36 μM. Molecular docking simulations were performed against the crystal epidermal growth factor receptor ensued the best docking scores and thought-provoking binding interactions compared to co-crystalized ligand Erlotinib.

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新型取代咪唑衍生物的设计、合成:细胞毒性和分子对接研究

以二酮、醛和乙酸铵为原料，一锅法合成了一系列新的5-(2-氯苯基)-4-(3,4-二甲氧基)-2-(取代苯基)- 1h -咪唑衍生物3(A -m)。通过IR、1H NMR、13C NMR和质谱分析确定了新化合物的结构。以顺铂为标准对照药，采用MTT法评价其对人宫颈癌HeLa细胞株的体外抗癌活性。化合物3e (R3 = 4-氰苯氧基)、3c (R3 = 2-硝基苯氧基)和3g (R2 = 4-硝基苯氧基);R3 =甲氧基)对HeLa细胞株的IC50值分别为2.7±0.4351 μM、4.824±0.8869 μM和6.877±0.6042 μM，而顺铂的IC50值为7.06±0.36 μM。与共晶配体厄洛替尼相比，晶体表皮生长因子受体进行了分子对接模拟，获得了最好的对接分数和发人深思的结合相互作用。

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来源期刊

Chemical Data Collections Chemistry-Chemistry (all)

CiteScore

6.10

自引率

0.00%

发文量

169

审稿时长

24 days

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