Access to a Library of 1,3-disubstituted-1,2,3-triazenes and Evaluation of their Antimicrobial Properties

Seck, I; Ndoye, Seyni; Ba, Lalla A.; Fall, Abdou Salam; Diop, Abdoulaye Dione; Ciss, Ismaïla; Ba, Abda; Sall, Cheikh; Diop, Amadou; Boye, Cheikh S B; Gómez, Generosa; Fall, Yagamare; Seck, Matar

doi:10.2174/1568026620666200127143005

Cited by 7 publications

(7 citation statements)

References 13 publications

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“…Hörner et al 35 reported the in vitro antibacterial activities of newly synthesized diaryltriazenes against standard bacteria (American Type Culture Collection, ATCC) and clinical isolates including multidrug-resistant (MDR) bacteria, and acute toxicity against Artemia salina. Initial experiments showed that these triazene compounds have biological activity against both methicillin-resistant Staphylococcus aureus (MRSA) and Mycobacterium smegmatis strains, with MIC values of 0.02 and 0.03 mg/mL, respectively 27,36 .…”

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confidence: 99%

“…The results showed that the compounds (triazene salts) had very strong activity against Burkitt lymphoma DAUDI and human colon adenocarcinoma HT-29 cells, with IC-50 values of 4.91 µg/mL and 5.59 µg/mL, respectively. Recently, Seck et al 36 reported new triazene compounds and evaluated their antimicrobial properties. All strains were sensitive, with the best MIC of 0.28 μM being observed against Escherichia coli, satisfactory against Pseudomonas aeruginosa, and 0.64 μM against Enterococcus faecalis.…”

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Assessment of the biological potential of diaryltriazene-derived triazene compounds

Figueiredo

Filho

Sodré

et al. 2021

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In the present study, novel, 1,3-diaryltriazene-derived triazene compounds were synthesized and tested. Triazenes are versatile and belong to a group of alkylating agents with interesting physicochemical properties and proven biological activities. This study describes the synthesis, molecular and crystalline structure, biological activity evaluation, and antifungal and antimicrobial potentials of 1,3-bis(X-methoxy-Y-nitrophenyl)triazenes [X = 2 and 5; Y = 4 and 5]. The antimicrobial and antifungal activities of the compounds were tested by evaluating the sensitivity of bacteria (American Type Culture Collection, ATCC) and clinical isolates to their solutions using standardized microbiological assays, cytotoxicity evaluation, and ecotoxicity tests. The antimicrobial potentials of triazenes were determined according to their minimum inhibitory concentrations (MICs); these compounds were active against gram-positive and gram-negative bacteria, with low MIC values. The most surprising result was obtained for T3 having the effective MIC of 9.937 µg/mL and antifungal activity against Candida albicans ATCC 90028, C. parapsilosis ATCC 22019, and C. tropicallis IC. To the best of our knowledge, this study is the first to report promising activities of triazene compounds against yeast and filamentous fungi. The results showed the potential utility of triazenes as agents affecting selected resistant bacterial and fungal strains.

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confidence: 99%

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confidence: 99%

Assessment of the biological potential of diaryltriazene-derived triazene compounds

Figueiredo

Filho

Sodré

et al. 2021

Sci Rep

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“…The 1,2,3-triazenes 1a, 1b, 2a, 2b, 3a, 3b, and 4, were obtained by the diazocopulation synthesis method [29] and the 1,4-disubstituted-1,2,3-triazoles 5a, 5b, 6a, 6b, and 8 by 1,3-dipolar cycloaddition [30][39] . The synthesis was carried out at the Organic Chemistry Laboratory of the Organic Chemistry Department of the University of Vigo.…”

Section: Ii1 Materialsmentioning

confidence: 99%

1,2,3-triazenes and 1,2,3-triazoles as antileishmanial, antitrypanosomal, and antiplasmodial agents

et al. 2022

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Trypanosomiasis, leishmaniasis and malaria are tropical diseases that affect poor populations and the classical drugs are toxic and select drug resistance. There is, therefore, an urgent need to find effective therapeutic agents accessible to developing countries that bear the brunt of morbidity and mortality.In this study, we evaluated the in vitro activities of fourteen 1,2,3-triazenes and 1,2,3triazoles against Trypanosoma brucei gambiense, Leishmania donovani and Plasmodium falciparum. Moreover, the synthesis of two new products among them will be described.The 1,4-disubstituted 1,2,3-triazenes showed better activities than 1,2,3-triazoles against Leishmania donovani with selectivity indexes greater than 100. Thus, compound 2b was the most effective one against axenic amastigote forms of Leishmania donovani LV9 with an IC 50 of 0.89 ± 0.41 M, and against the intramacrophagic amastigote forms, with an IC 50 value at 0.99 ± 0.36 M.Compounds 3a, a 1,2,3-triazene and 8, a triazole analogue of the cholesterol side chain, showed the best trypanocidal activities against Trypanosoma brucei gambiense with IC 50 of 3.45 ± 0.09 M and 3.99 ± 0.23 M, respectively.The most interesting result against the Plasmodium falciparum 3D7 strain was obtained with 5b with an IC 50 value of 1.29 ± 0.15 M.The present study revealed that 1,2,3-triazenes and 1,4-disubstituted 1,2,3-triazoles are chemical entities exhibiting an antiparasite potential that could lead to a new class of drug candidates.

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“…These compounds can be prepared by diazo copulation between diazonium salt and primary, or secondary amines [11] or Grignard reagents coupled with azide [12]. Due to its eco-friendly, the aqueous synthesis method has been largely used to prepare these compounds [13]. Aryl or alkyl triazenes with alkyl have been studied in medicinal and synthetic chemistry [13] [14].…”

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confidence: 99%

Spectroscopic Electrochemical Properties and DFT Calculation of 1-Aryltriazenes

Seck,

Sall,

Ndiaye

et al. 2023

IJOC

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Electrochromic materials are of great interest for their potential in eyewear protection and data storage devices, as they change colors in response to electrochemical switching. While many of the systems currently used are based on inorganic materials, organic materials such as triazenes have emerged as viable alternatives due to their unique properties, including optical properties. Triazenes are a class of organic compounds with three consecutive nitrogen atoms in an acyclic arrangement, and they have been used for a variety of applications in medicinal and synthetic chemistry. However, the effects of solvents on the UV-visible absorption spectrum of triazenes have not been fully investigated. The neutral molecules of 3,3-diisopropyl-1-phenyltriazene and 1-(4-chlorophenyl)-3-cyclopentyltriazene in acetonitrile, the UV-visible spectra corresponded respectively to HOMO → LUMO transitions with a large maximum absorption at 299.74 nm (4.1364 eV) and 299.57 nm (4.1387 eV) and the most intense oscillator strength (f = 0.6988) and (f = 0.7372). These results suggest that the electronic transitions of the compounds are highly influenced by the nature of the substituents on the triazene unit, as well as the solvent used in the experiment. The redox couple 0.92 and −0.44 V/Ag/AgCl is attributed to the phenyl group. Compound III showed an oxidation and reduction peak respectively −0.27 and −0.8 V/Ag/AgCl attributed to the phenyl molecule. The study concluded that all three compounds were electroactive and exhibited reversible characteristics with oxidizing/reducing couples. This study aims to contribute to research on the optical properties of triazenes compounds and the application of quantum chemical calculation methods for understanding their molecular structures. By investigating the solute-solvent interactions occurring in the solvation shell of the solutes, we

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Access to a Library of 1,3-disubstituted-1,2,3-triazenes and Evaluation of their Antimicrobial Properties

Cited by 7 publications

References 13 publications

Assessment of the biological potential of diaryltriazene-derived triazene compounds

Assessment of the biological potential of diaryltriazene-derived triazene compounds

1,2,3-triazenes and 1,2,3-triazoles as antileishmanial, antitrypanosomal, and antiplasmodial agents

Spectroscopic Electrochemical Properties and DFT Calculation of 1-Aryltriazenes

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