An efficient one-pot synthesis of 2-aminothiazoles via electrochemically oxidative α-C-H functionalization of ketones with thioureas

Li, Pei; Yang, Shangfeng; Fang, Zilin; Cui, Hongyuan; Tian, Hongyu; Sun, Baoguo; Zeng, Cheng‐Chu

doi:10.1016/j.jece.2022.107487

Cited by 7 publications

(3 citation statements)

References 44 publications

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“…Thiazole-containing heterocycles are fundamental scaffolds present in various natural and synthetic compounds. Thiazole substituted has a lot of interest due to its vast range of biological activity, such as anti-cancer [17][18][19], anti-bacterial [20], anti-inflammatory [21], anti-oxidant [22], and anti-epileptic [23]. On the other hand, the pyridine moiety also shows wide biological activities as anti-bacterial, anti-oxidant [24], and anticancer [25,26].…”

Section: Open Accessmentioning

confidence: 99%

Synthesis, biological evaluation and molecular docking of new triphenylamine-linked pyridine, thiazole and pyrazole analogues as anticancer agents

et al. 2022

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A new series of pyridine, thiazole, and pyrazole analogues were synthesized. The pyridone analogues 4a-e were synthesized by treating N-aryl-2-cyano-3-(4-(diphenylamino)phenyl)acrylamides 3a-e with malononitrile. Many 4-arylidene-thiazolidin-5-one analogues 6a-d were obtained by Knoevenagel reactions of 4-(diphenylamino)benzaldehyde (1) with their corresponding thiazolidin-5-one derivatives 5a-d. The structural elucidation of the products was proven by the collections of spectroscopic methods such as IR, 1H NMR, 13C NMR, and MS data. Their anti-cancer activity was examined against two cell lines, MDA-MB-231 (mammary carcinomas) and A-549 (lung cancer). Compared with cisplatin as a reference standard drug, 6-amino-4-(4-(diphenylamino)phenyl)-2-oxo-1-(p-tolyl)-1,2-dihydropyridine-3,5-dicarbonitrile (4b) and 6-amino-4-(4-(diphenylamino)phenyl)-1-(4-nitrophenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile (4e) exhibited better efficiency against the A-549 cell line, with IC50 = 0.00803 and 0.0095 μM, respectively. Also, these compounds 4b and 4e showed the most potency among the examined compounds against MDA-MB-231 with IC50 = 0.0103 and 0.0147 μM, respectively. The newly synthesized compounds were docked inside the active sites of the selected proteins and were found to demonstrate proper binding. 2-Cyano-2-(4,4-(diphenylamino)benzylidene)-5-oxo-3-phenylthiazolidin-2-ylidene)-N-(p-tolyl)acetamide (6c) offered the highest binding affinity (− 8.1868 kcal/mol) when docked into (PDB ID:2ITO), in addition to 2-cyano-N-(4-(diethylamino)phenyl)-2-(4-(4-(diphenylamino)benzylidene)-5-oxo-3-phenylthiazolidin-2-ylidene)acetamide (6a) gave the highest energy score (− 9.3507 kcal/mol) with (PDB ID:2A4L).

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Section: Open Accessmentioning

confidence: 99%

Synthesis, biological evaluation and molecular docking of new triphenylamine-linked pyridine, thiazole and pyrazole analogues as anticancer agents

et al. 2022

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“…Organic electrosynthesis has been recognized as a green, modern, and safe technique, since electrons can be used as an alternative for oxidants or reductants [30][31][32][33][34][35][36][37][38]. During our continuous interests in halide-mediated indirect electrolysis [39][40][41][42], we have achieved the in situ generation of α-iodocarbonyl ketones from constant current electrolysis (CCE) of ketones in the presence of iodide ions. It is worth noting that we have also reported an electrochemical method for the synthesis of 2-aminothiazoles via the one-pot direct α-C-H functionalization of ketones with thioureas [42].…”

Section: Introductionmentioning

confidence: 99%

“…During our continuous interests in halide-mediated indirect electrolysis [39][40][41][42], we have achieved the in situ generation of α-iodocarbonyl ketones from constant current electrolysis (CCE) of ketones in the presence of iodide ions. It is worth noting that we have also reported an electrochemical method for the synthesis of 2-aminothiazoles via the one-pot direct α-C-H functionalization of ketones with thioureas [42]. However, the reported method only tolerates aromatic and aliphatic ketones; the active methylene ketones were not suitable.…”

Section: Introductionmentioning

confidence: 99%

A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH₄I

Yang¹,

Li²,

Fang³

et al. 2022

Beilstein J. Org. Chem.

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The electrochemical preparation of 2-aminothiazoles has been achieved by the reaction of active methylene ketones with thioureas assisted by ᴅʟ-alanine using NH4I as a redox mediator. The electrochemical protocol proceeds in an undivided cell equipped with graphite plate electrodes under constant current conditions. Various active methylene ketones, including β-keto ester, β-keto amide, β-keto nitrile, β-keto sulfone and 1,3-diketones, can be converted to the corresponding 2-aminothiazoles. Mechanistically, the in situ generated α-iodoketone was proposed to be the key active species.

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Comparison of the interactions of fanetizole with pepsin and trypsin: Spectroscopic and molecular docking approach

Yue

Guo

et al. 2022

Journal of Molecular Liquids

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An efficient one-pot synthesis of 2-aminothiazoles via electrochemically oxidative α-C-H functionalization of ketones with thioureas

Cited by 7 publications

References 44 publications

Synthesis, biological evaluation and molecular docking of new triphenylamine-linked pyridine, thiazole and pyrazole analogues as anticancer agents

Synthesis, biological evaluation and molecular docking of new triphenylamine-linked pyridine, thiazole and pyrazole analogues as anticancer agents

A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH₄I

Comparison of the interactions of fanetizole with pepsin and trypsin: Spectroscopic and molecular docking approach

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An efficient one-pot synthesis of 2-aminothiazoles via electrochemically oxidative α-C-H functionalization of ketones with thioureas

Cited by 7 publications

References 44 publications

Synthesis, biological evaluation and molecular docking of new triphenylamine-linked pyridine, thiazole and pyrazole analogues as anticancer agents

Synthesis, biological evaluation and molecular docking of new triphenylamine-linked pyridine, thiazole and pyrazole analogues as anticancer agents

A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH4I

Comparison of the interactions of fanetizole with pepsin and trypsin: Spectroscopic and molecular docking approach

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A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH₄I