Solvent-Free Biginelli Condensation using Tungstate Sulfuric Acid: a Powerful and Reusable Catalyst for Selective Synthesis

Nasab, Rezvan Rezaee; Karami, Bahador; Khodabakhshi, Saeed

doi:10.9767/bcrec.9.2.6794.148-154

Cited by 5 publications

(3 citation statements)

References 31 publications

(29 reference statements)

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“…Based on the observed results, the SAR study indicated that, compounds 4d and 4e substituted with a NO 2 group at the 2 and 4-position of the phenyl ring showed the lowest cytotoxic activities which could be attributed to the withdrawing effects on the phenyl ring. Moreover, the compounds substituted with 6, 8-dichloro have shown better activity than 6-chloro substituted compounds which could be due to the inductive effect on the heterocycle compounds( 21 32 33 ).…”

Section: Discussionmentioning

confidence: 99%

Synthesis, characterization, cytotoxic screening, and density functional theory studies of new derivatives of quinazolin-4(3H)-one Schiff bases

et al. 2017

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A series of novel derivatives of quinazolinone Schiff bases were synthesized from benzoic acid starting material and evaluated for potential cytotoxic activities against the human breast adenocarcinoma (MCF-7) and the human colon adenocarcinoma (HT-29) cell lines. Compared to the reference drug, these compounds showed good cytotoxic activities against studied cell lines especially compounds 4d and 4e. The ground-state geometries of these compounds (4a-g) were optimized at the B3LYP/6–31G* density functional theory (DFT) level. Then maximum absorptions electron affinity, ionization potential, electronegativity (χ), energy gap (Egap), hardness (η), softness (S), electrophilicity (ω), and electrophilicity index (ωi) were calculated and discussed. The quantitative structure-activity relationship (QSAR) properties including the physicochemical parameters were also evaluated and studied. The computed properties of our novel synthesized compounds were compared with erlotinib compound.

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Section: Discussionmentioning

confidence: 99%

Synthesis, characterization, cytotoxic screening, and density functional theory studies of new derivatives of quinazolin-4(3H)-one Schiff bases

et al. 2017

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“…The presence of DNA gyrase in all bacteria except higher eukaryotes, makes it a drug target for antibacterial studies ( 4 5 ). Over the past decade, the quinazolin-4(3H)-one structural motifs containing azomethine (-C=N) functional group has become one of the main areas of interest due to possessing a wide spectrum of biological activities including antibacterial, antifungal, anticonvulsant, anti-inflammatory, antiviral, antihyperlipidemic, anti-tubercular, CNS depressant, anti-tumor, analgesic, antimalarial, and anti-cancer effects ( 6 7 ). Azomethine functional groups are formed when a primary amine reacts with a carbonyl compound ( 8 9 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antimicrobial evaluation and docking studies of some novel quinazolinone Schiff base derivatives

Nasab¹,

Mansourian²,

Hassanzadeh³

2018

Res Pharma Sci

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The quinazolin-4(3H)-one structural motif possesses a wide spectrum of biological activities. DNA gyrase play an important role in induction of bacterial death. It has been shown that many quinazolin-4(3H)-one derivatives have antibacterial effects through inhibition of DNA gyrase. Based on this information we decided to synthesize novel quinazolinone Schiff base derivatives in order to evaluate their antibacterial effects. A series of novel quinazolinone Schiff base derivatives were designed and synthesized from benzoic acid. The potential DNA gyrase inhibitory activity of these compounds was investigated using in silico molecular docking simulation. All new synthesized derivatives were screened for their antimicrobial activities against three species of Gram-negative bacteria including Escherichia coli, Pseudomonas aeruginosa, Salmonella entritidis and three species of Gram-positive bacteria comprising of Staphylococcus aurous, Bacillus subtilis, Listeria monocitogenes as well as for antifungal activities against Candida albicans using the conventional micro dilution method. Most of the compounds have shown good antibacterial activities, especially against E. coli at 128 µg/mL concentration while no remarkable antifungal activities were observed for these compounds. All the synthesized compounds exhibit dock score values between -5.96 and -8.58 kcal/mol. The highest dock score among them was -8.58 kcal/mol for compound 4c.

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“…The enzyme belongs to a superfamily of ATPases which is a known target for antibacterial agents since its blocking induces bacterial death ( 4 5 ). Quinazolines are a class of fused pyrimidine derivatives, which show a wide range of biological activities and used widely in the pharmaceutical industry, medicine and agriculture ( 6 7 8 9 10 11 ). Quinazolines act as an important backbone for a range of inhibitors of enzymes such as tyrosine kinase, thymidylate synthase and dihydrofolate reductase ( 12 13 14 ).…”

Section: Introductionmentioning

confidence: 99%

Docking study, synthesis and antimicrobial evaluation of some novel 4-anilinoquinazoline derivatives

et al. 2017

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A series of novel 4-anilinoquinazoline derivatives were designed and synthesized from benzoic acid through ring closure, chlorination or nucleophilic substitution. The structures of compounds were characterized by IR, 1H-NMR and mass spectroscopy. All synthesized derivatives were screened for their antimicrobial activities against Gram-positive (Staphylococcus aurous, Bacillus subtilis, Listeria monocitogenes) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa, Salmonella entritidis) bacteria and also for antifungal activities against Candida albicans using the conventional micro dilution method. Most of the compounds have shown good antibacterial activities, especially compound 4c having highest activities against E. coli at 32 μg/mL concentration while the tested compounds did not exhibited remarkable antifungal activities. The potential DNA gyrase inhibitory activity of these compounds was investigated in silico using molecular docking simulation method. All compounds showed good results especially compound 4c which showed the lowest ΔGbind results (-8.16 Kcal/mol).

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Solvent-Free Biginelli Condensation using Tungstate Sulfuric Acid: a Powerful and Reusable Catalyst for Selective Synthesis

Cited by 5 publications

References 31 publications

Synthesis, characterization, cytotoxic screening, and density functional theory studies of new derivatives of quinazolin-4(3H)-one Schiff bases

Synthesis, characterization, cytotoxic screening, and density functional theory studies of new derivatives of quinazolin-4(3H)-one Schiff bases

Synthesis, antimicrobial evaluation and docking studies of some novel quinazolinone Schiff base derivatives

Docking study, synthesis and antimicrobial evaluation of some novel 4-anilinoquinazoline derivatives

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