Synthesis, Antimicrobial Evaluation, and Docking Studies of Novel 4‐Substituted Quinazoline Derivatives as DNA‐Gyrase Inhibitors

Boyapati, Shireesha; Kulandaivelu, Umasankar; Sangu, Srinivas; Vanga, Malla Reddy

doi:10.1002/ardp.201000065

Cited by 38 publications

(13 citation statements)

References 29 publications

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“…For preparation of 3-(2-substituted-1,3,4-oxadiazol-5-yl)-β-carbolines 30 – 36 , 1-phenyl-β-carboline-3-carbohydrazide was subjected to reaction with a series of acids, followed by treatment with phosphorus oxychloride under reflux [ 30 ]. The compound 30 could be synthesized using other methodology [ 31 ]. The 1-phenyl-β-carboline-3-carbohydrazide was reacted with triethyl orthoformate under reflux to give the key intermediate hydrazonoformate 37 , which was used for further cyclization in pyridine under reflux to obtain the desired compound 30 .…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Bioactivity Evaluation of Novel β-carboline 1,3,4-oxadiazole Derivatives

Zhang

Jiang

et al. 2017

Molecules

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A series of novel β-carboline 1,3,4-oxadiazole derivatives were designed and synthesized, and the in vitro cytotoxic activity against Sf9 cells and growth inhibitory activity against Spodoptera litura were evaluated. Bioassay results showed that most of these compounds exhibited excellent in vitro cytotoxic activity. Especially, compound 37 displayed the best efficacy in vitro (IC50 = 3.93 μM), and was five-fold more potent than camptothecin (CPT) (IC50 = 18.95 μM). Moreover, compounds 5 and 37 could induce cell apoptosis and cell cycle arrest and stimulate Sf-caspase-1 activation in Sf9 cells. In vivo bioassay also demonstrated that compounds 5 and 37 could significantly inhibit larvae growth of S. litura with decreasing the weight of larvae and pupae. Based on these bioassay results, compounds 5 and 37 emerged as lead compounds for the development of potential insect growth inhibitions.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Bioactivity Evaluation of Novel β-carboline 1,3,4-oxadiazole Derivatives

Zhang

Jiang

et al. 2017

Molecules

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“…In all compounds it is clear that the hydrophobic pocket of the inhibitor binding site was occupied by 4-anilinoquinazoline or phenyl plus the groups substituted on these rings ( 28 29 30 ).…”

Section: Discussionmentioning

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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“…Substituted quinazolines were reported as isosters of quinolones to show a variety of antibacterial activities with DNA gyrase inhibition 16 . 4(3H)-Quinazolinones with 3-substitution has been reported to be associated with antimicrobial properties 17,18 .…”

Section: Research Articlementioning

confidence: 99%

Synthesis, Molecular Docking and Biological Evaluation of Substituted Quinazolinones as Antibacterial Agents

Mahato¹,

Shrivsatava²,

Shanthi³

2015

Chem Sci Trans

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A series of 7-chloro-2,3-disubstituted-4(3H)-quinazolinones (4a-j) were synthesized by the reaction of 3-amino-7-chloro-2-phenylquinazolin-4(3H)-one (3) with various amines in presence of formaldehyde. The starting material for the compounds was 2-amino-4-chloro benzoic acid. The structures of the compounds were characterized by IR, 1 H NMR, elemental analyses. Docking analysis of quinazolinone derivatives was done with DNA gyrase protein which was carried out by means of the AutoDockTools (ADT) v 1.5.4 and AutoDock v 4.2 programs. All compounds interacted with DNA gyrase protein. Preclinical evaluation of the compounds was ascertained by in silico toxicity, blood-brain barrier and drug like properties. All compounds were investigated for their antibacterial activity. Overall, compound (4b) showed better properties as a drug like candidate.

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Synthesis, Antimicrobial Evaluation, and Docking Studies of Novel 4‐Substituted Quinazoline Derivatives as DNA‐Gyrase Inhibitors

Cited by 38 publications

References 29 publications

Design, Synthesis and Bioactivity Evaluation of Novel β-carboline 1,3,4-oxadiazole Derivatives

Design, Synthesis and Bioactivity Evaluation of Novel β-carboline 1,3,4-oxadiazole Derivatives

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

Synthesis, Molecular Docking and Biological Evaluation of Substituted Quinazolinones as Antibacterial Agents

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