Synthesis and Biological Evaluation of Novel Di- and Trisubstituted Thiazole Derivatives

Kantminienė, Kristina; Parašotas, Irmantas; Urbonavičiūtė, Eglė; Anusevičius, Kazimieras; Tumosienė, Ingrida; Jonuškienė, Ilona; Vaickelionienė, Rita; Mickevičius, Vytautas

doi:10.3987/com-17-13714

Cited by 16 publications

(5 citation statements)

References 31 publications

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“…The success of the reaction was confirmed by the data of spectroscopy and the elemental analysis. In the 1 H NMR spectrum, the double sets of the peaks of the NHCO proton arise at 10.68, 10.79 and 12.57, 12.93 ppm with the intense ratio of 25:75, indicating the presence of a mixture of the Z/E isomers in DMSO- d 6 solution, where usually the Z -form predominates [ 48 , 49 ]. In the 1 H NMR spectrum of 14 the resonance of the Z isomer appeared at a lower-field area of the spectrum with the respect of the peak of the E -form [ 50 ].…”

Section: Resultsmentioning

confidence: 99%

“…The 1 H NMR spectra of the target hydrazones showed a mixture of two isomers in DMSO- d 6 solutions which form due to the presence of an amide bond in the structures and the restricted rotation around this bond. The resulting hydrazones exist as Z and E -amide conformers with an intensity ratio found to be 60:40 with the Z-conformer predominating [ 48 , 51 ] and arising up-field for almost all hydrazones except 16c based on NH signal integration. In the 1 H NMR spectrum of compound 16c with the thiophene substituent in the molecule, only one intense peak for NH proton at 11.34 ppm was found.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of novel sulphamethoxazole derivatives and exploration of their anticancer and antimicrobial properties

et al. 2023

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A series of new derivatives based on sulfamethoxazole were designed and synthesized in this study. The structures of the new compounds were confirmed based on a comprehensive characterization of spectral data by applied IR and 1H as well as 13C NMR spectroscopy. The prepared compounds were tested for their anticancer and antimicrobial properties. Hydrazone 16b demonstrated convincing anticancer effect against all tested cell cultures such as human prostate carcinoma PPC-1 and human kidney carcinoma CaKi-1 cell lines, and human fibroblasts HF, n = 3. The most promising compound 16b showed higher activity against CaKi-1 cell line than the anticancer drugs axitinib and pazopanib used to treat renal cancer. Also, it was more active in the PPC-1 cell line compared to the approved PARP inhibitor Olaparib. Hydrazone 16b was also found to possess good antimicrobial properties against gram-positive bacteria strains of Staphylococcus aureus, Staphylococcus epidermidis, as well as Bacillus cereus.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Synthesis of novel sulphamethoxazole derivatives and exploration of their anticancer and antimicrobial properties

et al. 2023

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“…The NMR spectra of 5a – g exhibited double sets of signals of the CONH group protons which is caused by a restricted rotation around the amide bond. The splitting of the proton signals indicates the formation of the Z/E isomers mixture in DMSO- d 6 solutions, where usually Z-form predominates [ 63 ]. The intense ratio of the signals of the isomers was found to be 65:35.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Novel Thiazole Derivatives Bearing β-Amino Acid and Aromatic Moieties as Promising Scaffolds for the Development of New Antibacterial and Antifungal Candidates Targeting Multidrug-Resistant Pathogens

et al. 2021

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Rapidly growing antimicrobial resistance among clinically important bacterial and fungal pathogens accounts for high morbidity and mortality worldwide. Therefore, it is critical to look for new small molecules targeting multidrug-resistant pathogens. Herein, in this paper we report a synthesis, ADME properties, and in vitro antimicrobial activity characterization of novel thiazole derivatives bearing β-amino acid, azole, and aromatic moieties. The in silico ADME characterization revealed that compounds 1–9 meet at least 2 Lipinski drug-like properties while cytotoxicity studies demonstrated low cytotoxicity to Vero cells. Further in vitro antimicrobial activity characterization showed the selective and potent bactericidal activity of 2a–c against Gram-positive pathogens (MIC 1–64 µg/mL) with profound activity against S. aureus (MIC 1–2 µg/mL) harboring genetically defined resistance mechanisms. Furthermore, the compounds 2a–c exhibited antifungal activity against azole resistant A. fumigatus, while only 2b and 5a showed antifungal activity against multidrug resistant yeasts including Candida auris. Collectively, these results demonstrate that thiazole derivatives 2a–c and 5a could be further explored as a promising scaffold for future development of antifungal and antibacterial agents targeting highly resistant pathogenic microorganisms.

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“…This splitting of the proton resonances indicates that in DMSO-d 6 , hydrazones exist as a mixture of Z/E isomers with respect to the hindered rotation around the amide bond. Usually, the Z isomer predominates [34,35,42]. In the 1 H NMR spectra, the NH protons of Z isomers resonate at a lower field with respect to the resonances attributed to E isomers [43].…”

Section: Chemistrymentioning

confidence: 99%

Novel N-Substituted Amino Acid Hydrazone-Isatin Derivatives: Synthesis, Antioxidant Activity, and Anticancer Activity in 2D and 3D Models In Vitro

Tumosienė

Jonuškienė

Kantminienė

et al. 2021

IJMS

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A series of novel mono and bishydrazones each bearing a 2-oxindole moiety along with substituted phenylaminopropanamide, pyrrolidin-2-one, benzimidazole, diphenylmethane, or diphenylamine fragments were synthesized, and their anticancer activities were tested by MTT assay against human melanoma A375 and colon adenocarcinoma HT-29 cell lines. In general, the synthesized compounds were more cytotoxic against HT-29 than A375. 3-((4-Methoxyphenyl)(3-oxo-3-(2-(2-oxoindolin-3-ylidene)hydrazinyl)propyl)amino)-N’-(2-oxoindolin-3-ylidene)propanehydrazide and (N’,N’’’)-1,1’-(methylenebis(4,1-phenylene))bis(5-oxo-N’-(2-oxoindolin-3-ylidene)pyrrolidine-3-carbohydrazide) were identified as the most active compounds against HT-29 in 2D and 3D cell cultures. The same compounds showed the highest antioxidant activity among the synthesized compounds screened by ferric reducing antioxidant power assay (FRAP). Their antioxidant activity is on par with that of a well-known antioxidant ascorbic acid.

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Synthesis and Biological Evaluation of Novel Di- and Trisubstituted Thiazole Derivatives

Cited by 16 publications

References 31 publications

Synthesis of novel sulphamethoxazole derivatives and exploration of their anticancer and antimicrobial properties

Synthesis of novel sulphamethoxazole derivatives and exploration of their anticancer and antimicrobial properties

Synthesis of Novel Thiazole Derivatives Bearing β-Amino Acid and Aromatic Moieties as Promising Scaffolds for the Development of New Antibacterial and Antifungal Candidates Targeting Multidrug-Resistant Pathogens

Novel N-Substituted Amino Acid Hydrazone-Isatin Derivatives: Synthesis, Antioxidant Activity, and Anticancer Activity in 2D and 3D Models In Vitro

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