Design, Synthesis, Characterization and Antimicrobial Evaluation of Some Heterocyclic Condensed Systems with Bridgehead Nitrogen from Thiazolotriazole Class

Bărbuceanu, Ștefania‐Felicia; Drăghici, Constantin; Bărbuceanu, Florica; Bancescu, Gabriela; Şaramet, Gabriel

doi:10.1248/cpb.c15-00379

Cited by 18 publications

(16 citation statements)

References 31 publications

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“…This reaction was carried out with acetone at room temperature in the presence of a base (NaOAc, Na 2 CO 3 ). The obtained thioesters can be converted to the corresponding thiazolo [3,2-b] [1,2,4]triazoles 1 under the action of sulfuric acid, [26][27][28][29][30] acetic anhydride in acidic medium, [21,[31][32][33] PPA, [34] pTSA, [35] or POCl 3. [36] Synthesis of thiazolo [3,2-b] [1,2,4]triazoles 1 proceeds through oxidative alkylation by acid condensation and MW radiation (Scheme 1).…”

Section: Synthesis Of Thiazolo [32-b][124]triazole Derivativesmentioning

confidence: 99%

“…The development of effective routes for obtaining new fused triazoles is relevant because of their wide range of bioactivity and as a consequence-great perspective for usage. Obtained compounds exhibit fungicidal, [26,37,39,[46][47][48] antimicrobial, [26,[37][38][39][46][47][48]56] analgesic, [27,34,[42][43][44] antinociceptive, [28] ulcerogenic, [28,43] antioxidant, [27,39] antiinflammatory, [27][28][29]34,[42][43][44] and anticancer [41] activity. Thiazolo [3,2-b] [1,2,4]triazoles have the ability to act as a urease inhibitor, [36] stabilizers of G-quadruplex [32] and may be used as cationic surfactants.…”

Section: Synthesis Of Thiazolo [32-b][124]triazole Derivativesmentioning

confidence: 99%

“…The best antifungal activity against C. glabrata fungus and C. albicans was MIC = 64 μg/mL. [26] Compounds of 1 have been evaluated for their antifungal activities against bacterial species including four standard fungi (Candida albicans, Candida tropicalis, Aspergillus niger, and Aspergillus flavus). Some representatives showed good activity with the minimal inhibitory concentration in the range of 100 to 200 mg/mL.…”

Section: Fungicidal Activitymentioning

confidence: 99%

“…The investigation showed good activity according to the measured minimum inhibitory concentration (MIC) in the range of 8 to 32 μg/mL. [26] For the investigation of antimicrobial activity of the derivatives of 1, Gram-positive (Staphylococcus aureus, Bacillus pumilis, Bacillus subtilis) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa) bacteria were taken. [37] The results revealed that all the synthesized compounds displayed variable inhibitory effects on the growth of the tested bacteria, with moderate to high activities.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

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Fused bicyclic 1,2,4‐triazoles with one extra sulfur atom: Synthesis, properties, and biological activity

Slivka

Korol

Fizer

2020

Journal of Heterocyclic Chem

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Fused heterocyclic systems with 1,2,4‐triazole scaffold arouse great interest from researchers in the branch of heterocyclic and medical chemistry because of their wide biological activities as they are considered as fungicidal, antimicrobial, analgesic, bronchodilators, antioxidant, anti‐inflammatory agents, and they are G‐quadruple stabilizers; the molecular docking data for coumarin‐containing 1,2,4‐triazoles indicate their ability to act as a urease inhibitor. Therefore, the present review aims to investigate new trends in the chemistry of heterocycles incorporating thiazolo[3,2‐b][1,2,4]triazoles, thiazolo[2,3‐c][1,2,4]triazoles, thiazino[5,1‐b][1,2,4]triazoles, thiazino[3,4‐b][1,2,4]triazoles, triazolothiazepines, and their biological characteristics. The main sections discuss: (a) the synthetic routes to the production of substituted fused heterocyclic systems, which include condensation reactions, multiple bond annulation, and the reactions of electrophilic heterocyclization. (b) Description of chemical and biological characteristics of these fused heterocycles.

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Section: Synthesis Of Thiazolo [32-b][124]triazole Derivativesmentioning

confidence: 99%

Section: Synthesis Of Thiazolo [32-b][124]triazole Derivativesmentioning

confidence: 99%

Section: Fungicidal Activitymentioning

confidence: 99%

Section: Antimicrobial Activitymentioning

confidence: 99%

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Fused bicyclic 1,2,4‐triazoles with one extra sulfur atom: Synthesis, properties, and biological activity

Slivka

Korol

Fizer

2020

Journal of Heterocyclic Chem

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“…Our previously research focused on the synthesis, characterization and biological evaluation, including antibacterial, antifungal and antioxidant activity [13][14][15][16] of some new compounds from 1,2,4-triazole-3-thiones and S-alkylated-1,2,4-triazole derivatives in order to discover new biological agents.…”

mentioning

confidence: 99%

S-Alkylated 1,2,4-Triazoles Derivatives Synthesis, spectral analysis and cytotoxicity evaluation

Bărbuceanu¹,

Olaru²,

Socea³

et al. 2019

Rev. Chim.

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This paper presents synthesis, characterization and cytotoxicity assessment of six S-alkylated 1,2,4-triazoles derivatives that were obtained by treatment of some 1,2,4-triazole-3-thiones containing in the molecule phenylsulfonylphenyl and propyl or 4-bromophenylsulfonylphenyl and 4-methoxyphenyl fragments with different alkylation agents (ethyl bromide, ethyl chloroacetate or phenacyl bromide) in basic media. The synthesized compounds were physico-chemically characterized and the IR, 1H-NMR, 13C-NMR spectra were consistent with the assigned structures. The cytotoxicity of S-alkylated derivatives was evaluated on Daphnia magna crustacean.

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Cyclodesulfurization: An Enabling Protocol for Synthesis of Various Heterocycles

et al. 2021

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Heterocycles closely intertwine chemistry with biology reflecting the presence of nitrogen‐based heterocyclic ring structure in nearly 75 % of small‐molecule drugs. The number of reported strategies for the synthesis of several “privileged scaffolds” has expanded, amongst which, cyclodesulfurization of thioureas offers a quick access to highly substituted heterocycles, thereby playing a role of an excellent tool in organic syntheses of natural products and pharmaceutically active compounds. This comprehensive review emphasizes the applications of cyclodesulfurization as an integral synthetic step in the synthesis of nitrogen, oxygen and sulfur‐containing heterocycles. Furthermore, a survey of cyclodesulfurizing agents reported since 2000 is comprehensively reviewed and summarized.

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Design, Synthesis, Characterization and Antimicrobial Evaluation of Some Heterocyclic Condensed Systems with Bridgehead Nitrogen from Thiazolotriazole Class

Cited by 18 publications

References 31 publications

Fused bicyclic 1,2,4‐triazoles with one extra sulfur atom: Synthesis, properties, and biological activity

Fused bicyclic 1,2,4‐triazoles with one extra sulfur atom: Synthesis, properties, and biological activity

S-Alkylated 1,2,4-Triazoles Derivatives Synthesis, spectral analysis and cytotoxicity evaluation

Cyclodesulfurization: An Enabling Protocol for Synthesis of Various Heterocycles

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