Synthesis and Biological Evaluation of New Ibuprofen‐1,3,4‐oxadiazole‐1,2,3‐triazole Hybrids

Rayam, Parsharamulu; Polkam, Naveen; Kummari, Bhaskar; Banothu, Venkanna; Gandamalla, Durgaiah; Yellu, Narsimha Reddy; Anireddy, Jaya Shree

doi:10.1002/jhet.3409

Cited by 20 publications

(11 citation statements)

References 63 publications

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“…Hence, we designed and synthesized PDCP as shown in Scheme . Monomer 1 was synthesized with two 1,2 3-triazoles and two primary amines to improve the water solubility and afford potential antibacterial activity. , Tris(4-bromophenyl)amine was modified with borate as monomer 2 to offer multivalent junction sites for obtaining hydrophobic skeleton scaffolds. After being modified, the two monomers were conjugated via a palladium-catalyzed Suzuki coupling reaction.…”

Section: Results and Discussionmentioning

confidence: 99%

Organic Polymer Nanoparticles with Primary Ammonium Salt as Potent Antibacterial Nanomaterials

Guo

Wang

Liu

et al. 2020

ACS Appl. Mater. Interfaces

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Bacterial infections induced by drug-resistant strains have become a global crisis. A membrane-disrupted mechanism is considered as an effective way to kill bacteria with little chance to trigger drug resistance. It is necessary to explore and develop new materials based on the membrane-disrupted mechanism to combat bacterial resistance. Here we report the design of organic nanoparticles based on a polymer (PDCP) as highly effective inhibition and bactericidal reagents. The PDCP is devised to have a hydrophobic skeleton and hydrophilic side chain modified with protonated primary amines, which could self-assemble to form organic nanoparticles (PDCP-NPs). By taking advantage of the large surface to volume ratio of nanoparticles, the synthesized PDCP-NPs have enriched positive charges and multiple membrane-binding sites. Research results display that PDCP-NPs have highly potent antibacterial activity in vitro and vivo, especially for Gram-negative bacteria with low toxicity against mammalian cells. This work design will inspire researchers to develop more membrane-disrupted bactericide and advance the applications of organic nanoparticles in the antibacterial area.

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Section: Results and Discussionmentioning

confidence: 99%

Organic Polymer Nanoparticles with Primary Ammonium Salt as Potent Antibacterial Nanomaterials

Guo

Wang

Liu

et al. 2020

ACS Appl. Mater. Interfaces

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“…1,2,3‐triazole is ubiquitous in numerous biologically active molecules and pharmaceuticals as triazoles are believed to be stable against metabolic degradation because of its structural and electronic similarity. On the other hand, 1,3,4‐oxadiazole ring is reported to improve ligand binding, flexibility, polarity, pharmacokinetics, in vivo metabolic profile, and aids in the design of molecules for the generation of newer derivatives that makes better interaction with receptors . Worthy to mention here that 1,3,4‐oxadiazole based anticancer drug, Zibotentan, is in late clinical trials, whereas, letrozole and anastrozole are triazole based drugs targeting aromatase that are used to treat breast cancer .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Anticancer Evaluation and DNA‐Binding Spectroscopic Insights of Quinoline‐Based 1,3,4‐Oxadiazole‐1,2,3‐triazole Conjugates

et al. 2019

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The present work involves a pharmacophore hybridization strategy to combine key biologically active scaffolds. The study led to the synthesis of quinoline based oxadiazole‐triazole conjugates with favorable physicochemical properties as anti‐cancer agents. Among the synthesized compounds 8(a–p), in vitro screening against a panel of four cancer cell lines identified compound 8k, with o‐chloro substitution on the phenyl ring, as potent against human lung carcinoma (A‐549) cells (IC50 =5.6 μM), while showing no significant cytotoxicity upto 200 μM concentration in normal cells. Compound 8 k with o‐chloro substitution induced nuclear morphological changes in A‐549 cells as visualized by DAPI (4,6‐diamidino‐2‐phenylindole) and was shown to bind firmly with A−T rich region in DNA. Changes in DNA topology studied through gel electrophoresis and groove mode of binding to ct‐DNA through multi‐spectroscopic techniques were observed, further validated by molecular docking studies. Overall, the study illustrates successful hybridization strategy leading to compound 8 k as promising anticancer agent for further structural optimization and biological evaluation.

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“…These compounds, mainly Di-Fluorophenyl (4g) and Naphthalene (4d), showed relatively acceptable antibacterial effects against Gram-Negative P. aeruginosa. In a study conducted by Rayam et al, it was reported that the antibacterial activity of new synthesis compounds revealed 2-(1-(4-isobutylphenyl)ethyl)-5-(((1-phenyl-1H-1,2,3triazol-4-yl)methyl)thio)-1,3,4-oxadiazole (8b) and demonstrated more potent antibacterial activity against E. coli and P. aeruginosa (19). In another study, Chortani et al showed how synthesis of novel 1, 3, 4-oxadiazole linked benzopyrimidinones conjugates.…”

Section: Discussionmentioning

confidence: 99%

Evaluation of the Antibacterial and Investigation of the Molecular Docking of New Derivatives of 1, 3, 4-Oxadiazole as Inhibitors of Quorum Sensing System in the Human PathogenPseudomonas Aeruginosa

Ghameshlouei

Ahrabi

Souldozi

et al. 2021

Avicenna J Clin Microbiol Infect

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Background: Oxadiazoles are a group of anti-inflammatory compounds that have a wide range of activity due to their higher efficacy. Pseudomonas aeruginosa is an opportunistic pathogen and a major pathogen of nosocomial infections. This study aimed to evaluate the antibacterial and investigation of the molecular docking of new derivatives of 1, 3, 4-oxadiazole against P. aeruginosa, in vitro & in silico. Materials and Methods: Four new derivatives were synthesized and added to our previous synthetic derivatives of 1, 3, 4-oxadiazole. The antibacterial activity of all derivatives was measured based on three standard species of P. aeruginosa using inhibition zone (IZ) and minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) methods. Then, employing the computational design of the drug by the molecular docking method, the inhibitory effect of synthetic compounds on the LasR regulatory protein of P. aeruginosa quorum sensing system was investigated, which plays an important role in regulating the expression of pathogenic genes in bacteria. Results: The chemical structures of new compounds were characterized by IR spectra and 1H-NMR. A variety of inhibitory effects were observed by the synthesized compounds – compound 4d and 4g, in particular. Also, the inhibitory effect of these two compounds on the LasR regulatory protein under the control of the quorum sensing system in P. aeruginosa was demonstrated by molecular docking. Conclusions: The results of this study showed that the two compounds containing the functional group of naphthalene and fluorophenyl have a significant effect on the inhibition of P. aeruginosa, as well as on the LasR protein of this bacterium.

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Synthesis and Biological Evaluation of New Ibuprofen‐1,3,4‐oxadiazole‐1,2,3‐triazole Hybrids

Cited by 20 publications

References 63 publications

Organic Polymer Nanoparticles with Primary Ammonium Salt as Potent Antibacterial Nanomaterials

Organic Polymer Nanoparticles with Primary Ammonium Salt as Potent Antibacterial Nanomaterials

Synthesis, Anticancer Evaluation and DNA‐Binding Spectroscopic Insights of Quinoline‐Based 1,3,4‐Oxadiazole‐1,2,3‐triazole Conjugates

Evaluation of the Antibacterial and Investigation of the Molecular Docking of New Derivatives of 1, 3, 4-Oxadiazole as Inhibitors of Quorum Sensing System in the Human PathogenPseudomonas Aeruginosa

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