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离子液体催化的二氢吡喃并[2,3-c]吡唑类多组分绿色合成法作为潜在的抗癌支架。

Ionic Liquid-Catalyzed Green Protocol for Multi-Component Synthesis of Dihydropyrano[2,3-c]pyrazoles as Potential Anticancer Scaffolds.

机构信息

Maulana Azad Post Graduate and Research Centre, Dr. Rafiq Zakaria Campus, Rauza Baug, Aurangabad 431001, India.

Departamento de Química Orgánica, Facultad de Ciencias, Universidad of Santiago de Compostela, Alfonso X el Sabio, 27002 Lugo, Spain.

出版信息

Molecules. 2017 Sep 28;22(10):1628. doi: 10.3390/molecules22101628.

DOI:10.3390/molecules22101628
PMID:28956863
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6151819/
Abstract

A series of 6-amino-4-substituted-3-methyl-2,4-dihydropyrano[2,3-]pyrazole-5-carbonitriles - were synthesized via one-pot, four-component condensation reactions of aryl aldehydes -, propanedinitrile (), hydrazine hydrate () and ethyl acetoacetate () under solvent-free conditions. We report herein the use of the Brønsted acid ionic liquid (BAIL) triethylammonium hydrogen sulphate [Et₃NH][HSO₄] as catalyst for this multi-component synthesis. Compared with the available reaction methodology, this new method has consistent advantages, including excellent yields, a short reaction time, mild reaction conditions and catalyst reusability. Selected synthesized derivatives were evaluated for in vitro anticancer activity against four human cancer cell lines viz. melanoma cancer cell line (SK-MEL-2), breast cancer cell line(MDA-MB-231), leukemia cancer cell line (K-562) and cervical cancer cell line (HeLa). Compounds , , , and exhibited promising anticancer activity against all selected human cancer cell lines, except HeLa. Molecular docking studies also confirmed and as good lead molecules. An in silico ADMET study of the synthesized anticancer agents indicated good oral drug-like behavior and non-toxic nature.

摘要

一系列 6-氨基-4-取代-3-甲基-2,4-二氢吡喃并[2,3-]吡唑-5-甲腈 - 通过一锅、四组分缩合反应合成芳醛、丙二腈()、水合肼()和乙酰乙酸乙酯()在无溶剂条件下。我们在此报告了使用 Brønsted 酸性离子液体(BAIL)三乙铵硫酸氢盐[Et₃NH][HSO₄]作为催化剂进行这种多组分合成。与现有的反应方法相比，这种新方法具有一致的优点，包括产率高、反应时间短、反应条件温和和催化剂可重复使用。选择合成的衍生物进行体外抗癌活性评估对四种人癌细胞系即黑素瘤癌细胞系(SK-MEL-2)、乳腺癌细胞系(MDA-MB-231)、白血病癌细胞系(K-562)和宫颈癌细胞系(HeLa)。化合物、、、和对所有选定的人癌细胞系均表现出有希望的抗癌活性，除了 HeLa。分子对接研究也证实和为良好的先导分子。合成抗癌剂的计算 ADMET 研究表明具有良好的口服药物样行为和非毒性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/34c6/6151819/842990a76d44/molecules-22-01628-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/34c6/6151819/5db1f0d090a6/molecules-22-01628-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/34c6/6151819/842990a76d44/molecules-22-01628-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/34c6/6151819/5db1f0d090a6/molecules-22-01628-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/34c6/6151819/842990a76d44/molecules-22-01628-g002.jpg

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