Synthesis of New Substituted Thiophene Derivatives and Evaluating their Antibacterial and Antioxidant Activities

Mehdhar, Fatima S.; Abdel‐Galil, Ebrahim; Saeed, Ali; Abdel‐Latif, Ehab; Ghani, Ghada E. Abd El

doi:10.1080/10406638.2022.2092518

Cited by 7 publications

(8 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Medicinal chemists employ structure–activity relationship studies to optimize compound structures, thereby enhancing efficacy and reducing toxicity. This approach has led to the development of new classes of antibiotics, including fluoroquinolones and oxazolidinones, which possess potent antibacterial properties [35]. Understanding the mechanisms underlying antibacterial activities is vital for the development of effective antibacterial agents.…”

Section: Resultsmentioning

confidence: 99%

Employing acetoacetamide as a key synthon for synthesizing novel thiophene derivatives and assessing their potential as antioxidants and antimicrobial agents

Almatari,

Saeed,

Abdel‐Ghani

et al. 2024

Journal of Heterocyclic Chem

Self Cite

View full text Add to dashboard Cite

The objective of this study is to synthesize novel heterocyclic scaffolds containing a thiophene moiety using easily accessible acetoacetamide as a key synthon. The reaction of acetoacetamide with diazonium salts resulted in the formation of the corresponding thiophene derivatives 4a–c. Additionally, the reaction of acetoacetamide derivative 3 with malononitrile, ethyl cyanoacetate, or 2‐cyanoacetamide, along with elemental sulfur, under refluxing in dioxane containing triethylamine afforded thiophene‐containing derivatives 5a–c. Furthermore, compound 3 reacted with phenyl isothiocyanate in dry dimethylformamide and K2CO3 to yield compound 7. In situ alkylation of the non‐isolable salt 6 was achieved by the addition of methyl iodide, resulting in the formation of methylthio‐thiophene‐2‐carboxamide 8. Compound 7 was employed with numerous alpha‐halogenated reagents in ethanol, affording thiazole derivative 9 and thiophene derivatives 10a and 10b, respectively. Moreover, compound 8 was reacted with hydrazine to produce the 1H‐pyrazole‐4‐carboxamide derivative 11. Additionally, refluxing acetoacetamide derivative 3 with malononitrile and/or ethyl cyanoacetate in dioxane, in the presence of catalytic amount of triethylamine afforded 4‐imino‐3,7‐dimethyl‐4H‐pyrido[1,2‐a]thieno[3,2‐e]pyrimidin‐9(5H)‐one derivatives 12a and 12b. Furthermore, the reactivity of acetoacetamide derivative 3 with 2‐cyanoacetohydrazide was investigated through refluxing the reactants in dioxane, which subsequently yielded the corresponding cyanoacetamide derivative 13. The chemical identity of the newly synthesized compounds was determined by employing infrared spectroscopy (IR), 1H NMR, and 13C NMR techniques. Newly synthesized heterocycles incorporating thiophenes were evaluated for their antioxidant and antimicrobial potentials. Notably, thiophene scaffolds 5a, 10b, 11, and 13 displayed notable antioxidant and antimicrobial activities.

show abstract

Section: Resultsmentioning

confidence: 99%

Employing acetoacetamide as a key synthon for synthesizing novel thiophene derivatives and assessing their potential as antioxidants and antimicrobial agents

Almatari,

Saeed,

Abdel‐Ghani

et al. 2024

Journal of Heterocyclic Chem

Self Cite

View full text Add to dashboard Cite

show abstract

“…[5,6] Many derivatives based on 2aminothiophenes were tested in mammalian carcinoma cells such as PC3 (prostate cancer), HepG2 (liver carcinoma), Hep-2 (laryngeal carcinoma), and MCF-7 (breast cancer) [7][8][9][10] (Figure 1). Furtheromore, the thiophene moiety also shows wide biological activities, such as antibacterial, [11][12][13] antioxidant, antifungal, SARS-CoV-2 main protease inhibition, [14][15][16][17] anti-inflammatory, [18] and anti-tubercular. [19] Thiophene-based dyes were also applied as sensitizers to many solar cells.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Biological Evaluation, and Docking Study of a New Series of Thiophene Derivatives Based on 3‐Oxobutanamidothiophene as an Anticancer Agent

Mehdhar,

Saeed,

Abdel‐Latif

et al. 2024

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

Herein, the constructing synthon 3‐oxobutanamidothiophene derivatives 2 a and 2 b were synthesized and utilized for building a wide variety of pyran, thiazole, pyrazole or pyrimidine ring heterocyclic compounds that can be used as anticancer medications. 3‐Oxobutanamidothiophene derivatives 2 a,b were coupled with 4‐substitutedphenyl diazonium chloride to produce the corresponding hydrazones derivatives 3 a–f. Various thiophene‐pyran derivatives 4 a,b were synthesized through the treatment of thiophene components 2 a,b with different arylidene‐malononitrile. 2‐Aminothiophene derivatives 5 were prepared via Gewald's reaction between 2 a,b, elemental sulfur, and various activated nitrile derivatives. The 3‐oxobutanamidothiophene derivatives 2 a,b were reacted with PhNCS and the potassium salt intermediates 6 a,b with ethyl bromoacetate to pick up the corresponding thiophene‐thiazolidin‐4‐one derivatives 7. Treatment of the conforming thiocarbamoyl compounds 8 a,b, which undergo heating with three types of α‐halogenated reagents to afford the corresponding substitutedthiophene‐3‐carboxamides 9 a,b. Condensation of keteneN,S‐acetals 10 a,b with hydrazines furnished the thiophene‐pyrazole‐4‐carboxamide hybrids 11 a,b, while condensation with urea and/or thiourea afforded the corresponding thiophene‐pyrimidine‐5‐carboxamides 12 a,b. The recently synthesized thiophene compounds were characterized there in vitro anticancer properties against HepG2 (hepatocellular carcinoma) and MDA‐MB‐231 (breast cancer) were evaluated. Molecular docking was also performed to predict the binding modes of synthesized derivatives with the good anticancer results designed as potential inhibitors for a specific target.

show abstract

“…Thiophene derivatives have garnered significant attention in the field of medicinal chemistry due to their diverse pharmacological properties and potential as bioactive agents [1][2][3]. In particular, their antimicrobial activity has become a focal point in light of the global threat of antimicrobial resistance [4][5][6].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structural Determination, Docking Study and Bioactivity of Novel Thiophene Derivatives

Mahyavanshi,

Lokhandwala,

Pandya

et al. 2024

ajc

View full text Add to dashboard Cite

The present study reveals 4-methyl-3-(propylamino)thiophene-2-carboxylic acid (Articaine acid) as precursor derivative to synthesize novel thiophene compounds to evaluate their biological activity. The synthesized compounds were subjected to comprehensive characterization techniques including mass spectra, NMR and IR spectroscopy, confirming their structural integrity. Their antimicrobial activity was assessed via minimum inhibitory concentration (MIC) assay against selected bacterial strains. The results emphasize the potential therapeutic applications of these thiophene analogues as efficacious antimicrobial agents, thereby encouraging further investigation. Molecular docking was used to examine thiophene derivative binding affinities on the S. aureus tyrosyl-tRNA synthetase protein and it was found that phenylethylamine derivatives had the highest binding affinity, followed by cyclohexyl methyl and benzylamine derivatives.

show abstract

Synthesis of New Substituted Thiophene Derivatives and Evaluating their Antibacterial and Antioxidant Activities

Cited by 7 publications

References 37 publications

Employing acetoacetamide as a key synthon for synthesizing novel thiophene derivatives and assessing their potential as antioxidants and antimicrobial agents

Employing acetoacetamide as a key synthon for synthesizing novel thiophene derivatives and assessing their potential as antioxidants and antimicrobial agents

Synthesis, Biological Evaluation, and Docking Study of a New Series of Thiophene Derivatives Based on 3‐Oxobutanamidothiophene as an Anticancer Agent

Synthesis, Structural Determination, Docking Study and Bioactivity of Novel Thiophene Derivatives

Contact Info

Product

Resources

About