Use of 2-(1-(4-Bromophenyl) Ethylidene)hydrazinecarbothioamide and 2-(5-Chloro-2-Oxoindolin-3-Ylidene)hydrazinecarbothioamide in the Syntheses of 2-Thiohydantoin, Pyrimidine Derivatives: Evaluation of Their Antimicrobial Activities.

El-Hady, H.Abd; nathali, HamedaSAl; Sayed, RefatEl

doi:10.21474/ijar01/5694

Cited by 3 publications

(2 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As an extension of our interest on the chemistry of 2-thiohydantoin, we reported here the synthesis of novel derivatives using ( E )-3-[1-(4-bromophenyl)ethylideneamino]-2-thioxoimidazolidin-4-one 1 as the key starting material. Compound 1 was prepared via reaction of ( E )-2-[1-(4-bromophenyl)ethylidene]hydrazinecarbothioamide in the presence of sodium acetate [ 27 , 28 ]. Alkylation of 1 with ethyl chloroacetate in the presence of anhydrous potassium carbonate gave ( E )-ethyl 2-{3-[1-(4-bromophenyl)ethylideneamino]-4-oxo-2-thioxoimidazolidin-1-yl}acetate 2 .…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis and evaluation of anticancer activity of novel 2-thioxoimidazolidin-4-one derivatives bearing pyrazole, triazole and benzoxazole moieties

Elhady

El‐Sayed

Al-nathali

2018

Chemistry Central Journal

View full text Add to dashboard Cite

A novel series of substituted 2-thiohydantoin incorporated with benzoimidazole, pyrazole, triazole and/or benzoxazole moieties has been synthesized using (E)-3-[1-(4-bromophenyl)ethylideneamino]-2-thioxoimidazolidin-4-one 1 as the key starting material. The key material 1 also, reacted with an acetic anhydride, aromatic aldehydes, secondary amines, formaldehyde and triethyl orthoformate to give the corresponding acetyl, chalcone, Mannich bases and ethoxymethylene derivatives, respectively. The structures of the novel compounds were confirmed by spectral data and elemental analysis. The cytotoxic activity of all synthesized compounds was assessed in vitro against human hepatocellular cancer cell line (HePG-2) and breast carcinoma cell line (MCF-7). The bioassay results revealed that compound 14 has the best activity against HePG-2 cell line (IC50 = 2.33 μg/mL), while compound 5 has the best activity against MCF-7 cell line (IC50 = 3.98 μg/mL). Electronic supplementary materialThe online version of this article (10.1186/s13065-018-0418-1) contains supplementary material, which is available to authorized users.

show abstract

Section: Resultsmentioning

confidence: 99%

Design, synthesis and evaluation of anticancer activity of novel 2-thioxoimidazolidin-4-one derivatives bearing pyrazole, triazole and benzoxazole moieties

Elhady

El‐Sayed

Al-nathali

2018

Chemistry Central Journal

View full text Add to dashboard Cite

show abstract

“…12 The presence of these double-bonded atoms with other functional groups results in particularly high density of binding sites for polar interactions and hydrogen bonds, which are responsible for their interesting biological properties. 13 A spectrum of their biological activity includes antifungal, 14,15 anticancer, [16][17][18] antidiabetic, 19,20 anti-inammatory, 21 antiviral, 22,23 anticonvulsant [24][25][26] and enzyme-inhibiting properties. 27,28 Another noteworthy feature of such cyclic systems is their strong polar and electron-withdrawing character, making them popular anchoring and electron-accepting groups in construction of merocyanine dyes for organic dye-sensitized solar cells (DSSC).…”

Section: Introductionmentioning

confidence: 99%

Highly efficient microwave synthesis of rhodanine and 2-thiohydantoin derivatives and determination of relationships between their chemical structures and antibacterial activity

et al. 2019

View full text Add to dashboard Cite

show abstract

Synthesis, Characterization, Anti-proliferative Evaluation, and DNA Flow Cytometry Analysis of Some 2-Thiohydantoin Derivatives

Elhady

Al-Shareef

2020

MRMC

View full text Add to dashboard Cite

Background and Objective: Due to the well-documented anti-proliferative activity of 2-thiohydantoin incorporated with pyrazole, oxadiazole, quinazoline, urea, β‑naphthyl carbamate and Schiff bases they are noteworthy in pharmaceutical chemistry. Methods: An efficient approach for the synthesis of a novel series of 2-thiohydantoin derivatives incorporated with pyrazole and oxadiazole has proceeded via the reaction of the acyl hydrazide with chalcones and/or triethyl orthoformate. Schiff bases were synthesized by the reaction of the acyl hydrazide with different aromatic aldehydes. Also, Curtius rearrangement was applied to the acyl azide to obtain the urea derivative, quinazoline derivative, and carbamate derivative. Results: The synthesized compounds structures were discussed and confirmed depending on their spectral data. The anticancer activity of these heterocyclic compounds was evaluated against the breast cancer cell line (MCF-7), where they showed variable activity. Compound 5d found to has a superior anticancer activity, where it has (IC50 = 2.07 ± 0.13 µg / mL) in comparison with the reference drug doxorubicin that has (IC50 = 2.79 ± 0.07 µg / mL). Then compound 5d subjected to further studies such as cell cycle analysis and apoptosis. Apoptosis was confirmed by the up-regulation of Bax, downregulation of Bcl-2, and the increase of the caspase 3/7percentage. Conclusion: Insertion of pyrazole, oxadiazole and, quinazoline moieties with 2-thiohydantoin moiety led to the enhancement of its anti-proliferative activity. Hence they can be used as anticancer agents.

show abstract

Use of 2-(1-(4-Bromophenyl) Ethylidene)hydrazinecarbothioamide and 2-(5-Chloro-2-Oxoindolin-3-Ylidene)hydrazinecarbothioamide in the Syntheses of 2-Thiohydantoin, Pyrimidine Derivatives: Evaluation of Their Antimicrobial Activities.

Cited by 3 publications

References 19 publications

Design, synthesis and evaluation of anticancer activity of novel 2-thioxoimidazolidin-4-one derivatives bearing pyrazole, triazole and benzoxazole moieties

Design, synthesis and evaluation of anticancer activity of novel 2-thioxoimidazolidin-4-one derivatives bearing pyrazole, triazole and benzoxazole moieties

Highly efficient microwave synthesis of rhodanine and 2-thiohydantoin derivatives and determination of relationships between their chemical structures and antibacterial activity

Synthesis, Characterization, Anti-proliferative Evaluation, and DNA Flow Cytometry Analysis of Some 2-Thiohydantoin Derivatives

Contact Info

Product

Resources

About