Synthesis and cytotoxic evaluation of some quinazolinone- 5-(4-chlorophenyl) 1, 3, 4-oxadiazole conjugates

Hassanzadeh, Farshid; Sadeghi‐Aliabadi, Hojjat; Jafari, Elham; Sharifzadeh, Azadeh; Dana, Nasim

doi:10.4103/1735-5362.268201

Cited by 19 publications

(4 citation statements)

References 18 publications

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“…As shown in Table 1, the greatest effect of compound 3a was observed on S. mutans with IZ=31.33 ± 0.50 mm, MIC=125 mg/mL, and MBC=250 mg/mL. This result can be due to the presence of chlorophenyl group in the main compound (18). The greatest effect of compound 3b was observed on S. aureus with IZ=24.66 ± 0.50 mm, MIC=500 mg/mL, and MBC=1000 mg/mL.…”

Section: Determination Of the In Vitro Antibacterial And Antifungal Propertiesmentioning

confidence: 87%

Synthesis and Antimicrobial Evaluation of New Series of 1,3,4-Oxadiazole Containing Cinnamic Acid Derivatives

SarveAhrabi

Ahrabi

Souldozi

2021

Avicenna J Clin Microbiol Infect

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Background: New drugs must be designed and synthesized for combating resistant pathogens. In this study, antibacterial and antifungal activities of 4 new derivatives of 1,3,4-oxadiazole were assessed against 8 bacterial and 2 fungal pathogens. Methods: To this end, the cinnamic acid derivatives were dissolved in acetonitrile solvent and N-iso-ciano-imino-triphenyl-phosphorane was added to the above-mentioned solution, followed by applying Petroleum ether and Ethyl acetate as solvent and base. Then, antimicrobial susceptibility tests were used to determine inhibition zone diameter, minimum inhibitory concentration, the minimum bactericidal concentration (MBC), and minimum fungicidal concentration (MFC) values. Results: The chemical structure of all compounds was characterized with infrared spectra, 1H-NMR, and 13C-NMR. A variety of inhibitory effects were observed by the synthesized compounds. Methoxyphenyl derivative (3c) affected bacterial strains, especially Streptococcus mutans. Other compounds also had antibacterial properties. Additionally, compound 3c showed the greatest effect on fungal samples, especially Aspergillus flavus. Conclusions: In general, our new derivatives of 1,3,4-oxadiazole are able to destroy Gram-positive bacteria. In addition, developing new derivatives of 1,3,4-oxadiazole in future research can improve therapeutic properties. It seems that with the addition of other functional groups and increasing the destructive power of compounds, inhibitory effects on fungal samples can also be observed.

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Section: Determination Of the In Vitro Antibacterial And Antifungal Propertiesmentioning

confidence: 87%

Synthesis and Antimicrobial Evaluation of New Series of 1,3,4-Oxadiazole Containing Cinnamic Acid Derivatives

SarveAhrabi

Ahrabi

Souldozi

2021

Avicenna J Clin Microbiol Infect

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“…A literature survey reveals that 1, 3, 4- oxadiazole is an interesting heterocyclic scaffold for the development of new anticancer agents ( 28 30 31 ). In the present study, some amide and imine derivatives of oxadiazole were synthesized in two steps, along with some previously prepared oxadiazole derivatives ( 17 ), and the cytotoxic effects were evaluated on two cell lines at different concentrations.…”

Section: Discussionmentioning

confidence: 99%

Synthesis, cytotoxic evaluation, and molecular docking studies of some new 1, 3, 4-oxadiazole-based compounds

et al. 2020

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Background and purpose: Oxadiazole-derived compounds have been shown to have a wide range of pharmacological activities. 2, 5-Disubstituted 1, 3, 4-oxadiazole derivatives have occupied a specific place in the design of anti-proliferative agents. In the present work a series of 2, 5-disubstituted 1, 3, 4-oxadiazoles derivatives containing amide group has been synthesized via a two-step reaction. Experimental approach: A mixture of substituted carboxylic acid derivatives, semicarbazide, and phosphorus oxychloride in reflux condition yielded 2-amino-5-aryl-1, 3, 4-oxadiazole derivatives. Acylation of the amino group of the resultant oxadiazole with 6-chloronicotinoyl chloride in dry tetrahydrofuran/pyridine afforded the final products. The synthesized molecules were docked in the active sites of the epidermal growth factor receptor tyrosine kinase domain (PDB: 1M17) crystal structure to study the possible interactions with the active site. Cytotoxic activities of final products against HeLa and MCF-7 cells were also assessed by MTT assay. Findings/Results: Compounds IIb, IIc, and IIe had a considerable cytotoxic activity with IC50 values of 19.9, 35, and 25.1 μM, respectively against HeLa cells. The highest docking score was -7.89 kcal/mol for compound IIe . Conclusion and implications: Compound IIe exhibited remarkable cytotoxic activity against the two tested cell lines particularly HeLa cells which was in accordance with the in silico ΔG bind result but further evaluations are necessary to prove these findings.

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“…The mixture was basified by anhydrous potassium carbonates (0.02 mol) then, ethyl chloroacetate (0.02 mol) was added and the reaction contents were reflux for 24 h and monitored by TLC. The precipitates were collected through filtration and the organic solution was concentrated in vacuo to give a crude product which crystallized by chloroform ( 5 27 19 ) ( Scheme 1 ).…”

Section: Methodsmentioning

confidence: 99%

“…Five-membered heterocyclics are used as a pivotal scaffold of many compounds in medicinal chemistry due to their similarity with biologically active compounds within our body and provide a wide range of biological activities such as anticonvulsant, anticancer, antimicrobial, and anti-inflammatory effects ( 2 3 ). In this family, azoles, including 1, 3, 4-oxadiazoles, 1, 3, 4-thiadiazoles and 1, 2, 4-triazoles have been involved as “privileged” construction in plentiful therapeutic areas particularly anticancer chemotherapy ( 2 3 4 5 6 7 8 9 ). Literature survey indicated that a minor alteration in the structure of 1,3, 4-oxadiazoles, 1,2, 4-triazoles and 1,3, 4-thiadiazines can lead to changes in their biological activities ( 10 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and cytotoxic activity evaluation of some new 1, 3, 4-oxadiazole, 1, 3, 4-thiadiazole and 1, 2, 4- triazole derivatives attached to phthalimide

Hassanzadeh

Jafari

Shojaei

et al. 2021

Research in Pharmaceutical Sciences

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Background and purpose: In the last few decades, nitrogen-rich heterocyclic compounds such as 1, 3, 4-thiadiazoles, 1, 2, 4-triazoles and 1, 3, 4-oxadiazoles have received considerable attention because of their notable biological properties, especially cytotoxic effects. The small molecules of mentioned azole derivatives revealed very intensive antitumor activity. In addition, phthalimide-thiadiazole and naphthalimide-triazole hybrid derivatives have shown remarkable cytotoxic effects. According to these observations, some of the hybrid derivatives containing the phthalimide-five-membered azoles were prepared in three steps in this research. Experimental approach: The thiol group of azoles was treated with ethyl chloroacetate which was followed by a reaction with hydrazine hydrate to provide acid hydrazide derivatives. Subsequently, the corresponding acid hydrazides were utilized to prepare the final derivatives through the reaction with phthalic anhydride. Cytotoxic activity of final compounds was evaluated against MCF-7 and HeLa cell lines using MTT assay. Findings/Results: Compound 3d containing two phthalimide moieties in its structure showed a significant improvement in cytotoxic activity with an IC 50 value of 29 μM against HeLa cell line. Compounds 3a-3c showed less cytotoxic effects against both cell lines. Conclusion and implications: The combination of the thiadiazole nucleus with two phthalimide structures increased the cytotoxic activity against the HeLa cell line. This increase in cytotoxic activity is probably due to its being more lipophilic characteristic and interaction of this derivative with the biological targets of two directions.

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Synthesis and cytotoxic evaluation of some quinazolinone- 5-(4-chlorophenyl) 1, 3, 4-oxadiazole conjugates

Cited by 19 publications

References 18 publications

Synthesis and Antimicrobial Evaluation of New Series of 1,3,4-Oxadiazole Containing Cinnamic Acid Derivatives

Synthesis and Antimicrobial Evaluation of New Series of 1,3,4-Oxadiazole Containing Cinnamic Acid Derivatives

Synthesis, cytotoxic evaluation, and molecular docking studies of some new 1, 3, 4-oxadiazole-based compounds

Synthesis and cytotoxic activity evaluation of some new 1, 3, 4-oxadiazole, 1, 3, 4-thiadiazole and 1, 2, 4- triazole derivatives attached to phthalimide

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