The synthesis of imidazoles and evaluation of their antioxidant and antifungal activities

Ghorbani‐Vaghei, Ramin; Izadkhah, Vida; Mahmoodi, Jafar; Karamian, Roya; Khoei, Masoumeh Ahmadi

doi:10.1007/s00706-018-2167-1

Cited by 15 publications

(8 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Imidazole derivatives, being di-, tri-, and tetra-substituted, have shown antioxidant activity through different antioxidant methodologies [5][6][7]. This is a useful property to counteract oxidative stress, a condition when reactive oxygen species (ROS) overcome the natural cellular antioxidant defense system.…”

Section: Introductionmentioning

confidence: 99%

In Vitro and In Silico Screening of 2,4,5-Trisubstituted Imidazole Derivatives as Potential Xanthine Oxidase and Acetylcholinesterase Inhibitors, Antioxidant, and Antiproliferative Agents

et al. 2020

View full text Add to dashboard Cite

The employment of privileged scaffolds in medicinal chemistry supplies scientists with a solid start in the search for new and improved therapeutic molecules. One of these scaffolds is the imidazole ring, from which several derivatives have shown a wide array of biological activities. A series of 2,4,5-triphenyl imidazole derivatives were synthesized, characterized, and evaluated in vitro as antioxidant molecules using 1,1-diphenyl-2-picrylhydrazyl (DPPH.) and 2-2′-azino-bis-(3-ethylbenzothiazoline-6-sulfonate) (ABTS.+) assays, acetylcholinesterase (AChE) and xanthine oxidase (XO) inhibitors as well as antiproliferative agents. Additional in silico studies such as docking and determination of their absorption, distribution, metabolism, and excretion (ADME) properties were calculated. Compounds 3 and 10 were the most active antioxidants in both the DPPH and ABTS assays (EC50 of 0.141 and 0.174 mg/mL, and 0.168 and 0.162 mg/mL, respectively). In the enzymatic inhibition, compound 1 showed the best activity, inhibiting 25.8% of AChE at a concentration of 150 μg/mL, and compound 3 was the most active XO inhibitor with an IC50 of 85.8 μg/mL. Overall, against the six different evaluated cancerous cell lines, molecules 2, 10, and 11 were the most antiproliferative compounds. In silico predictions through docking point out 11, and ADME analysis to 11 and 12, as good candidates for being lead compounds for further derivations.

show abstract

Section: Introductionmentioning

confidence: 99%

In Vitro and In Silico Screening of 2,4,5-Trisubstituted Imidazole Derivatives as Potential Xanthine Oxidase and Acetylcholinesterase Inhibitors, Antioxidant, and Antiproliferative Agents

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Also, the steric hindrance of substituents on substrates has no significant effect on the rate of the reactions. All the products' structure was characterized by 1 H-NMR, 13 C-NMR, IR, CHN analysis, and melting points. The IR spectrum of 2-cyano-2-(2-phenyl-1,5-di-p-tolyl-1H-imidazole-4-yl)acetamide 6a showed absorption bands at 3453 cm −1 for NH 2 , 2245 cm −1 for CN, 1682 cm −1 for C O, and 1647 cm −1 for C N groups.…”

Section: Resultsmentioning

confidence: 99%

“…Peaks are reported in wavenumbers (Cm −1 ). All of the NMR spectra were recorded on a Varian model UNITY Inova 500 MHz ( 1 H: 500, 13 C: 125 MHz) NMR spectrometer. Chemical shifts of 1 H and 13 C-NMR are reported in parts per million (ppm) from tetramethylsilane (TMS) as an internal standard in DMSO-d 6 and CDCl 3 as solvents.…”

Section: Discussionmentioning

confidence: 99%

“…[1] imidazole and pyrimidine analogs have been reported to exhibit a wide range of unique biological activities such as anti-HIV, [2,3] anticancer, [4,5] antihypertensive, [6] antiviral, [7,8] antibacterial, [9,10] anti-tubercular, [11] antimicrobial, [12] and antioxidant. [13,14] Moreover, nature utilizes the unique type of pyrimidine ring in several biological molecules such as nucleic acids, DNA, and RNA. [15] Also, the imidazole nucleus has been found in many biological systems such as histidine, [16] histamine, and biotin.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of 1,2,4,5‐tetrasubstituted imidazoles and 2,4,5,6‐tetrasubstituted pyrimidines: three‐component, the one‐pot reaction of arylamidines, malononitrile, and arylglyoxals or aryl aldehydes

Mehrabi

Hajipour

Rezazadeh‐Jabalbarezi

et al. 2020

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

A highly efficient one‐pot synthesis of the 1,2,4,5‐tetrasubstituted imidazoles and 2,4,5,6‐tetrasubstituted pyrimidines through an arylamidine, malononitrile, and carbonyl compound by using Et3N in CH3CN at reflux conditions was developed. The nature of the carbonyl compounds were different; when the carbonyl compound was arylglyoxal or aryl aldehyde, 1,2,4,5‐tetrasubstituted imidazole and 2,4,5,6‐tetrasubstituted pyrimidine were achieved respectively.

show abstract

“…Remarkably, imidazole and thiazole nuclei exhibited a wide variety of different significant biological activities. Imidazole derivatives achieved potential results as effective drugs such as antioxidants [ 2 ], anti-inflammatory [ 3 ], antimicrobial [ 4 ], and so on. Another unique five-membered ring is thiazole.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Molecular Docking, and Evaluation Antioxidant and Antimicrobial Activities for Novel 3-Phenylimidazolidin-4-One and 2-Aminothiazol-4-One Derivatives

et al. 2022

View full text Add to dashboard Cite

On our way to discovering and developing compounds that have an antioxidant impact compared to ascorbic acid and other biological activities, we designed, synthesized, and evaluated a new series of heterocyclic moieties drugs (1–11) as antioxidants and antimicrobial agents. As starting moieties, these new candidates were derived from two promising heterocyclic compounds, imidazoldin-4-one and thiazol-4-one. Firstly, diphenylimidazol 1 was obtained because of the cyclo condensation one-pot ternary reaction of urea, aniline, and chloroacetic acid under thermal conditions. Out of this starting compound, we could design and create new vital rings such as purine and triazine as in compounds 5 and 6, respectively. Secondly, the start thiazole derivative 7 was obtained from the intermolecular cyclization of thiourea, chloroacetic acid, p-nitobezaldehyde in the presence of sodium acetate. We synthesized various derivatives from this second starting compound 7 by being subjected to different reagents such as aniline, phenylenediamine, phenylhydrazine, and barbituric acid to yield 8, 9, 10, and 11, respectively. Using ascorbic acid as the standard compound, the pharmacological testing for antioxidant activity assessment of the produced derivatives was evaluated against ABTS (2,20-azinobis (3-ethylbenzothiazoline-6-sulfonic acid). Candidate 6 exhibited the best activity as an antioxidant agent compared to ascorbic acid as a reference compound. Moreover, all compounds were evaluated as antimicrobial agents against a series of bacteria and fungi. Among all synthesized compounds, compound 6 achieved high efficiency against two types of fungi and four kinds of bacteria, as Clotrimazole and Ampicillin were used as the reference agents, respectively. All chemical structures of the novel synthesized candidates were unequivocally elucidated and confirmed utilizing spectroscopical and elemental investigations.

show abstract

The synthesis of imidazoles and evaluation of their antioxidant and antifungal activities

Cited by 15 publications

References 32 publications

In Vitro and In Silico Screening of 2,4,5-Trisubstituted Imidazole Derivatives as Potential Xanthine Oxidase and Acetylcholinesterase Inhibitors, Antioxidant, and Antiproliferative Agents

In Vitro and In Silico Screening of 2,4,5-Trisubstituted Imidazole Derivatives as Potential Xanthine Oxidase and Acetylcholinesterase Inhibitors, Antioxidant, and Antiproliferative Agents

Synthesis of 1,2,4,5‐tetrasubstituted imidazoles and 2,4,5,6‐tetrasubstituted pyrimidines: three‐component, the one‐pot reaction of arylamidines, malononitrile, and arylglyoxals or aryl aldehydes

Design, Synthesis, Molecular Docking, and Evaluation Antioxidant and Antimicrobial Activities for Novel 3-Phenylimidazolidin-4-One and 2-Aminothiazol-4-One Derivatives

Contact Info

Product

Resources

About