Synthesis and antimicrobial evaluation of cationic low molecular weight amphipathic 1,2,3-triazoles

Bakka, Thomas Aleksander; Strøm, Morten B.; Andersen, Jeanette Hammer; Gautun, Odd R.

doi:10.1016/j.bmcl.2017.01.092

Cited by 15 publications

(3 citation statements)

References 44 publications

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“…The triazole‐hydrazone (Rambabu et al, 2016), 1,2,3‐triazole‐silatrane (Singh et al, 2018), 1,2,3‐triazole‐nucleoside (Malkowski et al, 2017; Tachallait et al, 2018), 1,2,3‐triazole‐guanidine (Bakka et al, 2017), 1,2,3‐triazole‐biotin (Paparella et al, 2018), 1,2,3‐triazole‐betulin (Bębenek et al, 2017), and 1,2,3‐triazole‐pseudoaglycon (Szűcs et al, 2017) are the some other hybrids which possessed weak to moderate activities but were less active than the reference drugs.…”

Section: Biologically Active 123‐triazole‐o‐heterocycle Hybridsmentioning

confidence: 99%

A minireview of 1,2,3‐triazole hybrids with O‐heterocycles as leads in medicinal chemistry

Saroha

Kumar

et al. 2021

Chem Biol Drug Des

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Over the past few decades, the dynamic progress in the synthesis and screening of heterocyclic compounds against various targets has made a significant contribution in the field of medicinal chemistry. Among the wide array of heterocyclic compounds, triazole moiety has attracted the attention of researchers owing to its vast therapeutic potential and easy preparation via copper and ruthenium-catalyzed azide-alkyne cycloaddition reactions. Triazole skeletons are found as major structural components in a different class of drugs possessing diverse pharmacological profiles including anti-cancer, anti-bacterial, anti-fungal, anti-viral, anti-oxidant, anti-inflammatory, anti-diabetic, anti-tubercular, and anti-depressant among B. subtilis(MIC) 26a 1.56 µg/mL 26b 3.125 µg/mL 26c 3.125 µg/mL S. aureus(MIC) 26a 1.56 µg/mL 26b 3.125 µg/mL 26c 1.56 µg/mL A. nigar(MIC) 26d 3.125 µg/mL 26e 3.125 µg/mL C. albians(MIC) 26d 3.125 µg/mL 26e 3.125 µg/mL gram negative bacteria(MIC) 26a 3.125 µg/mL 26b 3.125 µg/mL 26c 3.125 µg/mL

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Section: Biologically Active 123‐triazole‐o‐heterocycle Hybridsmentioning

confidence: 99%

A minireview of 1,2,3‐triazole hybrids with O‐heterocycles as leads in medicinal chemistry

Saroha

Kumar

et al. 2021

Chem Biol Drug Des

View full text Add to dashboard Cite

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“…That is, the presence of two cationic groups and two lipophilic groups of sufficient bulk to exert broad-spectrum activity [14]. Among these were β-amino amides [15,16], cyclic tetrapeptides [16], barbiturates [17] and others [18,19]. The barbituric acid framework 1 has proven to be a valuable scaffold for the preparation of highly active antimicrobials [17,20], and we were curious if our previous results would translate to other scaffold structures.…”

Section: Introductionmentioning

confidence: 97%

Investigation of Tetrasubstituted Heterocycles Reveals Hydantoins as a Promising Scaffold for Development of Novel Antimicrobials with Membranolytic Properties

et al. 2022

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“…presented in this publication was prepared in parallel to a similar library of amphiphiles based on 1,2,3-triazole phthalimides. 21…”

Section: Introductionmentioning

confidence: 99%

Methyl propiolate and 3-butynone: Starting points for synthesis of amphiphilic 1,2,3-triazole peptidomimetics for antimicrobial evaluation

Bakka

Strøm

Andersen

et al. 2017

Bioorganic & Medicinal Chemistry

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A library of 29 small 1,4-substituted 1,2,3-triazoles was prepared for studies of antimicrobial activity. The pharmacophore model investigated with these substrates was based on small peptidomimetics of antimicrobial peptides and antimicrobials isolated from marine organisms from sub-arctic regions. Using methyl 1,2,3-triazole-carboxylates and 1,2,3-triazole methyl ketones prepared through "click" chemistry we were able to synthesize the different cationic amphiphiles through three steps or less. Several structural modifications to the lipopohilic side and hydrophilic sides of the amphiphiles were investigated and compared with regards to antimicrobial activity and cytotoxicity in particular. The most promising amphiphile 10f displayed minimum inhibitory concentrations (MICs) between 4-16µg/mL against Gram-positive Enterococcus faecalis, Staphylococcus aureus, Streptococcus agalacticae, and Gram-negative Escherichia coli and Pseudomonas aeruginosa. The decent level of antimicrobial activity and biofilm inhibition, short synthesis, and accessible reagents, makes this type of amphiphilic mimics interesting leads for further development.

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Synthesis and antimicrobial evaluation of cationic low molecular weight amphipathic 1,2,3-triazoles

Cited by 15 publications

References 44 publications

A minireview of 1,2,3‐triazole hybrids with O‐heterocycles as leads in medicinal chemistry

A minireview of 1,2,3‐triazole hybrids with O‐heterocycles as leads in medicinal chemistry

Investigation of Tetrasubstituted Heterocycles Reveals Hydantoins as a Promising Scaffold for Development of Novel Antimicrobials with Membranolytic Properties

Methyl propiolate and 3-butynone: Starting points for synthesis of amphiphilic 1,2,3-triazole peptidomimetics for antimicrobial evaluation

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