Antimicrobial and Anti-biofilm Activity of Thiourea Derivatives Incorporating a 2-Aminothiazole Scaffold

Stefańska, Joanna; Nowicka, Grażyna; Struga, Marta; Szulczyk, Daniel; Kozioł, Anna E.; Augustynowicz–Kopeć, Ewa; Napiórkowska, Agnieszka; Bielenica, Anna; Filipowski, Wojciech; Filipowska, Anna; Drzewiecka, Aleksandra; Giliberti, Gabriele; Madeddu, Silvia; Boi, Stefano; Colla, Paolo La; Sanna, Giuseppina

doi:10.1248/cpb.c14-00837

Cited by 52 publications

(39 citation statements)

References 34 publications

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“…The free amino group offered a possibility for further reaction with isothiocyanates to obtain the thiourea derivatives 1e – 7e . This reaction was performed in acetonitrile similar to previously reported thiourea derivative syntheses [ 32 , 34 ].…”

Section: Resultsmentioning

confidence: 99%

“…Ureas, thioureas, hydrazones, semicarbazides or thiosemicarbazides are found to posses similar properties and are useful as starting material in the synthesis of the three title heterocyclic arrangements and their structural modification. Prompted by this fact and encouraged by the results of recent studies [ 32 , 33 , 34 ] we decided to design synthetic paths to produce a battery of 1,3,4-oxadiazole, 1,3,4-thiadiazole, and 1,2,4-triazole derivatives.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Biological Activities of Ethyl 2-(2-pyridylacetate) Derivatives Containing Thiourea, 1,2,4-triazole, Thiadiazole and Oxadiazole Moieties

et al. 2017

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Thirty six novel heterocyclic derivatives of ethyl 2-(2-pyridylacetate) were efficiently synthesized. The new compounds involve the linkage of a 2-pyridyl ring with thiosemicarbazide (compounds 1–7), 1,2,4-triazole (compounds 1a–7a), 1,3,4-thiadiazole (compounds 1b–7b), and 1,3,4-oxadiazole (compounds 1f–7f) moieties. The last group of compounds 1e–7e involves the connection of a 2-pyridyl ring with 1,2,4-triazole and thiourea. 1H-NMR, 13C-NMR and MS methods were used to confirm the structures of the obtained derivatives. The molecular structures of 3, 3b, 7a and 7f were further confirmed by X-ray crystallography. All obtained compounds were tested in vitro against a number of microorganisms, including Gram-positive cocci, Gram-negative rods and Candida albicans. In addition, the obtained compounds were tested for cytotoxicity and antiviral activity against HIV-1.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Activities of Ethyl 2-(2-pyridylacetate) Derivatives Containing Thiourea, 1,2,4-triazole, Thiadiazole and Oxadiazole Moieties

et al. 2017

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“…Cell viability was determined after 96 h at 37°C by the MTT method. 15) As far as stationary monolayers (analogous to those which support the replication of the other RNA and DNA viruses) are concerned, MDBK and BHK cells were seeded in 24-well plates at an initial density of 6×10 5 and 1×10 6 cells/mL, re- Cell lines derived from human haematological tumours [CD4+ human T-cells containing an integrated human Tcell leukemia virus type-1 (HTLV-1) genome (MT-4); CD4+ human acute T-lymphoblastic leukaemia (CCRF-CEM), human splenic B-lymphoblastoid cells (WIL-2NS), human acute B-lymphoblastic leukaemia (CCRF-SB)] were seeded at an initial density of 1×10 5 cells/mL in 96 well plates in RPMI-1640 medium supplemented with 10% fetal calf serum (FCS), 100 units/mL penicillin G and 100 µg/mL streptomycin. Cell viability was determined after 96 h at 37°C by the MTT method.…”

Section: Methodsmentioning

confidence: 99%

“…Absorbance was measured at 490 nm using a microplate reader (using Epoch microplate reader, BioTek Inc.) equipped with Gen5 software (BioTech Instruments, Inc.). 5) Compounds mediated cytotoxicity expressed as the LDH release (%) was determined by the following equation: [(A test sample−A low control)/(A high control−A low control)]×100% (A-absorbance); where "low control" were cells in DMEM with 2% FBS without tested compounds, and "high control" were cells incubated in DMEM with 2% FBS with 10% Triton X-100 (100% LDH release).…”

Section: Methodsmentioning

confidence: 99%

Statistical Analysis of the Impact of Molecular Descriptors on Cytotoxicity of Thiourea Derivatives Incorporating 2-Aminothiazole Scaffold

et al. 2016

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Chemical reactivity descriptors and lipophilicyty (log P) were evaluated via semi-empirical method for the quantum calculation of molecular electronic structure (PM3) in order to clarify the structure-cytotoxic activity relationships of disubstutited thioureas. Analysed compounds were obtained by the linkage of 2-aminothiazole ring, thiourea and substituted phenyl ring. The detailed examination was carried out to establish correlation between descriptors and cytotoxic activity against the MT-4 cells for 11 compounds. For the most active compounds (6 compounds) cytotoxic activity against three cancer cell lines (CCRF-CEM, WIL-2NS, CCRF-SB) and normal human cell (HaCaT) was determined. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) reduction and lactate dehydrogenase (LDH) release were assessed. Regression analysis revealed that electrophilicity index and chemical potential significantly contributed to expain the thioureas cytotoxic potential.

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“…These findings encouraged us to go further with our ongoing studies on the thiourea derivatives, since that many biological properties have been already discovered by our team among this group of compounds . In this study, we have synthesized new thiourea and thiazolidinone derivatives with 1,3‐benzothiazole‐2‐yl scaffold.…”

Section: Introductionmentioning

confidence: 99%

New thiourea and 1,3‐thiazolidin‐4‐one derivatives effective on the HIV‐1 virus

et al. 2017

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Thiourea derivatives have been reported to possess many biological activities, among them antiviral and antitumoral properties. As part of our continuing effort to develop new active compounds, we report the synthesis and the evaluation of new fifteen thiourea derivatives with 1,3-benzothiazole-2-yl moiety, among them a group of biologically active (1-7) also underwent cyclization to 1,3-thiazolidin-4-ones. Molecular structure of four compounds (4, 13, 15 and 3a) was determined by an X-ray crystallography. We here report the evaluation of their cytotoxicity against human leukaemia/lymphoma- and solid tumour-derived cell lines and of their antiviral activity against HIV-1 and representatives of ssRNA and dsDNA viruses. Derivative 5 showed an interesting activity against HIV-1 wild type and against variants carrying clinically relevant mutations. A colorimetric enzyme immunoassay clarified its mode of action as a non-nucleoside inhibitor of the reverse transcriptase.

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Antimicrobial and Anti-biofilm Activity of Thiourea Derivatives Incorporating a 2-Aminothiazole Scaffold

Cited by 52 publications

References 34 publications

Synthesis and Biological Activities of Ethyl 2-(2-pyridylacetate) Derivatives Containing Thiourea, 1,2,4-triazole, Thiadiazole and Oxadiazole Moieties

Synthesis and Biological Activities of Ethyl 2-(2-pyridylacetate) Derivatives Containing Thiourea, 1,2,4-triazole, Thiadiazole and Oxadiazole Moieties

Statistical Analysis of the Impact of Molecular Descriptors on Cytotoxicity of Thiourea Derivatives Incorporating 2-Aminothiazole Scaffold

New thiourea and 1,3‐thiazolidin‐4‐one derivatives effective on the HIV‐1 virus

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