Synthesis and antimicrobial activity of a novel hybrid benzo[b]thiophene-1,2,3-triazole analogues

Thotla, Krishna; Noole, Venkatagiri; Reddy, Ch. Krishna

doi:10.1016/j.cdc.2020.100361

Cited by 9 publications

(3 citation statements)

References 20 publications

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“…Evaluation of their in vitro antifungal activity showed that compound I′1 with ZI = 9.7 mm and compound I′2 with ZI = 12.3 mm were the most potent antifungal agents against A. niger and S. rolfsii at a concentration of 100 mg mL −1 , respectively. However, both compounds showed weaker antifungal activity than the reference drug, ketoconazole (Thotla et al, 2020). Sampath et al (2020) synthesized multiple 1,2,3-triazoles tethered 3-hydroxy-2-oxindoles under ball-milling conditions by merging aldol condensation with the click reaction.…”

Section: Fluconazole Analogsmentioning

confidence: 99%

Click chemistry beyond metal‐catalyzed cycloaddition as a remarkable tool for green chemical synthesis of antifungal medications

Tahghighi,

Azerang

2024

Chem Biol Drug Des

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Click chemistry is widely used for the efficient synthesis of 1,4‐disubstituted‐1,2,3‐triazole, a well‐known scaffold with widespread biological activity in the pharmaceutical sciences. In recent years, this magic ring has attracted the attention of scientists for its potential in designing and synthesizing new antifungal agents. Despite scientific and medical advances, fungal infections still account for more than 1.5 million deaths globally per year, especially in people with compromised immune function. This increasing trend is definitely related to a raise in the incidence of fungal infections and prevalence of antifungal drug resistance. In this condition, an urgent need for new alternative antifungals is undeniable. By focusing on the main aspects of reaction conditions in click chemistry, this review was conducted to classify antifungal 1,4‐disubstituted‐1,2,3‐triazole hybrids based on their chemical structures and introduce the most effective triazole antifungal derivatives. It was notable that in all reactions studied, Cu(I) catalysts generated in situ by the reduction in Cu(II) salts or used copper(I) salts directly, as well as mixed solvents of t‐BuOH/H2O and DMF/H2O had most application in the synthesis of triazole ring. The most effective antifungal activity was also observed in fluconazole analogs containing 1,2,3‐triazole moiety and benzo‐fused five/six‐membered heterocyclic conjugates with a 1,2,3‐triazole ring, even with better activity than fluconazole. The findings of structure–activity relationship and molecular docking of antifungal derivatives synthesized with copper‐catalyzed azide–alkyne cycloaddition (CuAAC) could offer medicinal chemistry scientists valuable data on designing and synthesizing novel triazole antifungals with more potent biological activities in their future research.

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Section: Fluconazole Analogsmentioning

confidence: 99%

Click chemistry beyond metal‐catalyzed cycloaddition as a remarkable tool for green chemical synthesis of antifungal medications

Tahghighi,

Azerang

2024

Chem Biol Drug Des

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“…Most of the compounds have moderate-to-good antifungal activity against A. niger in comparison to the standard medicine Ravuconazole [124]. otla et al [125] synthesized a new series of Benzo[b] thiophene triazoles with high yields from various azides with propargyl derivatives of benzothiophene, and most of them displayed significant antifungal activity against the fungi tested (Sclerotium rolfsii and Aspergillus niger) (Figure 60).…”

Section: 23-triazole Linked To Other Heterocyclicmentioning

confidence: 99%

A Recent Overview of 1,2,3-Triazole-Containing Hybrids as Novel Antifungal Agents: Focusing on Synthesis, Mechanism of Action, and Structure-Activity Relationship (SAR)

Marzi

Farjam

Kazeminejad

et al. 2022

Journal of Chemistry

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A pharmacophore system has been found as 1,2,3-triazole, a five-membered heterocycle ring with nitrogen heteroatoms. These heterocyclic compounds can be produced using azide-alkyne cycloaddition processes catalyzed by ruthenium or copper. The bioactive compounds demonstrated antitubercular, antibacterial, anti-inflammatory, anticancer, antioxidant, antiviral, and antidiabetic properties. This heterocycle molecule, in particular, with one or more 1,2,3-triazole cores has been found to have the most powerful antifungal effects. The goal of this review is to highlight recent developments in the synthesis and structure-activity relationship (SAR) investigation of this prospective fungicidal chemical. Also there have been explained drugs and mechanism of action of a triazole compound with antifungal activity. This review will be useful in a variety of fields, including medicinal chemistry, organic chemistry, mycology, and pharmacology.

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“…Because of their special structural characteristics, triazoles are considered as important class of heterocyclic compounds showing interesting biological, pharmaceutical and therapeutic activities including antifungal [2] , antimicrobial [3] , [4] , [5] , [6] , [7] , [8] , anti-cancer [9] , anticonvulsant [10] , antihypertensive [11] , and anti-viral [12] . In this regard many drugs containing triazole moiety are manufactured, which of them Ribavirin or Copegus (an antiviral), Alprazolam (an anxiolytic), Letrozole (an anticancer), and Flusilazole (an organosilicon fungicide) [13] are examples ( Fig.…”

Section: Introductionmentioning

confidence: 99%

Agar-entrapped sulfonated DABCO: Agelly acidic catalyst for the acceleration of one-pot synthesis of 1,2,4-triazoloquinazolinone and some pyrimidine derivatives

Moghaddampour

Shirini

Langarudi

2021

Journal of Molecular Structure

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Highlights Structurally functionalized 1,2,4-triazoloquinazolinone and some pyrimidine derivatives were synthesized by agar-entrapped sulfonated DABCO as a non-metal catalyst. The moisture-resistant property of the catalyst were investigated. A simple purification step was performed to achieve high purity. The reusability of the catalyst was investigated during three runs for all compounds.

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Synthesis and antimicrobial activity of a novel hybrid benzo[b]thiophene-1,2,3-triazole analogues

Cited by 9 publications

References 20 publications

Click chemistry beyond metal‐catalyzed cycloaddition as a remarkable tool for green chemical synthesis of antifungal medications

Click chemistry beyond metal‐catalyzed cycloaddition as a remarkable tool for green chemical synthesis of antifungal medications

A Recent Overview of 1,2,3-Triazole-Containing Hybrids as Novel Antifungal Agents: Focusing on Synthesis, Mechanism of Action, and Structure-Activity Relationship (SAR)

Agar-entrapped sulfonated DABCO: Agelly acidic catalyst for the acceleration of one-pot synthesis of 1,2,4-triazoloquinazolinone and some pyrimidine derivatives

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