New Progress in Azole Compounds as Antimicrobial Agents

Zhang, Huizhen; Gan, Lin-Ling; Wang, Hui; Zhou, Cheng‐He

doi:10.2174/1389557516666160630120725

Cited by 120 publications

(37 citation statements)

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“…Structural changes and the basic interactions identified from the 1,3,4‐oxadiazole scaffold, such as Sulfisoxazole (antibacterial), Oxacillin (antibiotic), Linezolid (antibacterial), Toloxatone (antidepressant), Furazolidone (antibacterial), Raltegravir (anti‐HIV) as shown in Figure . Oxadiazole compounds as the bioisostere of benzimidazoles and thiazoles, imidazoles, tetrazoles, and triazoles have attracted increasing attention. Recently, numerous researches have been devoting to oxadiazole compounds as a medicinal agent with an intent to discover novel chemical scaffold compounds with low toxicity, high bioactive and excellent pharmacokinetic property .…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of 2‐(2‐Bromo‐3‐nitrophenyl)‐5‐phenyl‐1,3,4‐oxadiazole Derivatives as Possible Anti‐Breast Cancer Agents

Ananth

Manikandan²,

Rajan³

et al. 2020

Chemistry & Biodiversity

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Breast Cancer (BCa) is the most often diagnosed cancer among women who were in the late 1940’s. Breast cancer growth is largely dependent on the expression of estrogen and progesterone receptor. Breast cancer cells may have one, both, or none of these receptors. The treatment for breast cancer may involve surgery, hormonal therapy (Tamoxifen, an aromatase inhibitor, etc.) and oral chemotherapeutic drugs. The molecular docking technique reported the findings on the potential binding modes of the 2‐(2‐bromo‐3‐nitrophenyl)‐5‐phenyl‐1,3,4‐oxadiazole derivatives with the estrogen receptor (PDB ID: 3ERT). The 1,3,4‐oxadiazole derivatives 4a–4j have been synthesized and described by spectroscopic method. 2‐(2‐Bromo‐6‐nitrophenyl)‐5‐(4‐bromophenyl)‐1,3,4‐oxadiazole (4c) was reconfirmed by single‐crystal XRD. All the compounds have been tested in combination with generic Imatinib pharmaceutical drug against breast cancer cell lines isolated from Caucasian woman MCF‐7, MDA‐MB‐453 and MCF‐10A non‐cancer cell lines. The compounds with the methoxy (in 4c) and methyl (in 4j) substitution were shown to have significant cytotoxicity, with 4c showing dose‐dependent activation and decreased cell viability. The mechanism of action was reported by induced apoptosis and tested by a DNA enzyme inhibitor experiment (ELISA) for Methyl Transferase. Molecular dynamics simulations were made for hit molecule 4c to study the stability and interaction of the protein−ligand complex. The toxicity properties of ADME were calculated for all the compounds. All these results provide essential information for further clinical trials.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of 2‐(2‐Bromo‐3‐nitrophenyl)‐5‐phenyl‐1,3,4‐oxadiazole Derivatives as Possible Anti‐Breast Cancer Agents

Ananth

Manikandan²,

Rajan³

et al. 2020

Chemistry & Biodiversity

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“…[19][20][21][22][23] Pharmaceutical chemistry has produced many drugs containing a tetrazole ring as a structural element (in order to treat, AIDS, cancer and tuberculosis for example). [24][25][26][27][28] One key study by Kanakaraju and Suresh demonstrated an in vitro antimicrobial and cytotoxic evaluation of tetrazole derivatives. The results showed that the maximum antimicrobial activity was observed with seleniumcontaining tetrazole derivatives, whereas sulphur-containing tetrazole derivatives exhibited appreciable cytotoxicity.…”

Section: Introductionmentioning

confidence: 99%

Adenine Derivatives for Regenerable Antibacterial Surface Applications Based on A−T Base Pairing

et al. 2020

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Surface contamination is a major concern in the design, fabrication, and application of biomaterials. In this work, a series of new adenine derivatives were synthesized in a three‐step method with the goal of protecting the functional materials against microbial adhesion. Initially, 9‐(chloroalkyl)‐9H‐purin‐6‐amine compounds were synthesized from adenine. Then, these compounds were reacted with potassium thiocyanate or potassium selenocyanate. In the last step, adenine derivatives incorporating a tetrazole ring were synthesized via the cycloaddition of sodium azide with thiocyano or selenocyano derivatives. The antimicrobial activity of the compounds was evaluated by using the minimal inhibitory concentration method. Furthermore, the effect of the compounds on pBR322 plasmid DNA was studied using gel electrophoretic mobility measurements. The antimicrobial assay showed that some of the synthesized compounds exerted vigorous antibacterial and antifungal activities. Further experiments indicated that seleno‐adenine derivatives have higher antimicrobial and DNA effect than other derivatives. The surfaces activated by the adenine derivative demonstrated antibacterial activity resisting bacterial attachment in order to remove dead bacteria from the surface. All results showed that some of these adenine derivatives have an antibacterial activity and the potential for further applications, for example as a smart surface coating that prevents bacterial adhesion to biomaterials.

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“…To this end, we decided to introduce at this position a 1,2,3‐triazole core, a well‐known pharmacophore . Indeed, recent studies have revealed that triazole containing nucleosides exert a broad spectrum of pharmacological activities including antiviral, antimicrobial, antiproliferative, and antitumor properties …”

Section: Introductionmentioning

confidence: 99%

Concise synthesis and antibacterial evaluation of novel 3‐(1,4‐disubstituted‐1,2,3‐triazolyl)uridine nucleosides

Tachallait

Bouyahya

Talha

et al. 2018

Archiv der Pharmazie

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We report herein a simple and efficient synthesis of a new series of antibacterial uridine nucleosides. The strategy involved a sequential silylation/N-glycosylation/ N-propargylation procedure of uracil 1 for preparing the dipolarophile 5 in good yield.A series of novel uridine-[1,2,3]triazole nucleosides 6a-j were efficiently synthesized via the copper-catalyzed azide-alkyne cycloaddition (CuAAC) from dipolarophile 5 with different selected azides. The reactions were carried out under both conventional and ultrasonic irradiation conditions. In general, improvements were observed when reactions were carried out under sonication. Their antibacterial potential has been evaluated by means of a micro-dilution assay against either Gram-positive or Gram-negative bacteria. Compounds 6i and 6j have shown significant bactericidal activity against Staphylococcus aureus (MIC = 10 and 6 μM, respectively), and 6hagainst Escherichia coli (MIC = 8 μM). Moreover, antibacterial kinetic assays showed that 6i and 6j significantly reduced the S. aureus growth rate at the MIC concentration, after 6 h, compared to their deprotected analogs, 6k and 6l, respectively. Compound 6h also significantly reduced the growth of E. coli. These antibacterial effects may be related to the penetrating properties of these compounds, as revealed by the leakage of nucleic acids from the sensitive strains.

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New Progress in Azole Compounds as Antimicrobial Agents

Cited by 120 publications

References 0 publications

Design, Synthesis, and Biological Evaluation of 2‐(2‐Bromo‐3‐nitrophenyl)‐5‐phenyl‐1,3,4‐oxadiazole Derivatives as Possible Anti‐Breast Cancer Agents

Design, Synthesis, and Biological Evaluation of 2‐(2‐Bromo‐3‐nitrophenyl)‐5‐phenyl‐1,3,4‐oxadiazole Derivatives as Possible Anti‐Breast Cancer Agents

Adenine Derivatives for Regenerable Antibacterial Surface Applications Based on A−T Base Pairing

Concise synthesis and antibacterial evaluation of novel 3‐(1,4‐disubstituted‐1,2,3‐triazolyl)uridine nucleosides

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