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            -(Imidazole/Benzimidazole)-Pyridine Derivatives: Synthesis, Structure and Antimycobacterial Activity

Antoci, Vasilichia; Diaconu, Dumitrela; Zbancioc, Gheorghiță; Moldoveanu, Costel; Mangalagiu, Violeta; Mantu, Dorina; Aricu, Aculina; Mangalagiu, Ionel I.

doi:10.4155/fmc-2019-0063

Cited by 39 publications

(35 citation statements)

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“…Encouraged by our recent results in the field of (di)azine with antimicrobial activity [ 11 , 15 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 ], we report here the design, synthesis, antibacterial and antifungal evaluation of some newly hybrid quinoline-sulfonamide complexes.…”

Section: Introductionmentioning

confidence: 99%

Hybrid Quinoline-Sulfonamide Complexes (M2+) Derivatives with Antimicrobial Activity

et al. 2020

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Two new series of hybrid quinoline-sulfonamide complexes (M2+: Zn2+, Cu2+, Co2+ and Cd2+) derivatives (QSC) were designed, synthesized and tested for their antimicrobial activity. The synthesis is straightforward and efficient, involving two steps: acylation of aminoquinoline followed by complexation with metal acetate (Cu2+, Co2+ and Cd2+) or chloride (Zn2+). The synthesized QSC compounds were characterized by FTIR and NMR spectroscopy and by X-ray diffraction on single crystal. The QSC compounds were preliminary screened for their antibacterial and antifungal activity and the obtained results are very promising. In this respect, the hybrid N-(quinolin-8-yl)-4-chloro-benzenesulfonamide cadmium (II), considered as leading structure for further studies, has an excellent antibacterial activity against Staphylococcus aureus ATCC25923 (with a diameters of inhibition zones of 21 mm and a minimum inhibitory concentration (MIC) of 19.04 × 10−5 mg/mL), a very good antibacterial activity against Escherichia coli ATCC25922 (with a diameters of inhibition zones of 19 mm and a MIC of 609 × 10−5 mg/mL), and again an excellent antifungal activity against Candida albicans ATCC10231 (with a diameters of inhibition zones of 25 mm and a MIC of 19.04 × 10−5 mg/mL).

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Section: Introductionmentioning

confidence: 99%

Hybrid Quinoline-Sulfonamide Complexes (M2+) Derivatives with Antimicrobial Activity

et al. 2020

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“…Over the past few decades, considerable efforts have been directed toward the synthesis and evaluation of the biological properties of bis-imidazole derivatives, a class of heterocyclic compounds displaying significant levels of antifungal, antibacterial, and antimycobacterial activities [196][197][198][199][200][201][202][203].…”

Section: Bis-imidazolesmentioning

confidence: 99%

“…In 2020, Mangalagiu, Mangalagiu, and coworkers designed, synthesised, and evaluated the antimycobacterial activity of bis(imidazole)pyridines 331a-g [202]. The efficient and straightforward synthesis of these new quaternary salts was carried out by an approach in which a solution of 3 eq of 1H-imidazole (260) or 4-nitro-1H-imidazole (332) in a mixture of THF and DMF was treated with a suspension of 3.6 eq of NaH in THF and 1 eq of 2,6-bis(chloromethyl)pyridine (333) at room temperature.…”

Section: Scheme 64 Synthesis Of Amine-derived Bis-imidazoles 323a-i and Hydrochlorides 324a-dmentioning

confidence: 99%

“…The efficient and straightforward synthesis of these new quaternary salts was carried out by an approach in which a solution of 3 eq of 1H-imidazole (260) or 4-nitro-1H-imidazole (332) in a mixture of THF and DMF was treated with a suspension of 3.6 eq of NaH in THF and 1 eq of 2,6-bis(chloromethyl)pyridine (333) at room temperature. The resulting compounds 334a-g were then treated with a solution of 2.4-2.8 eq of α-halocarbonyl derivatives 335a-g giving rise to the required quaternary salts 331a-g in yields ranging from 50 to 92% (Scheme 67) [202]. Notably, most of these compounds were found to possess significant antibacterial activity against six Gram-negative bacteria, namely E. coli, S. Typhimurium, P. aeruginosa, A. calcoaceticus, S. pyogenes, and S. aureus, and against four Gram-positive bacteria, namely B. subtilis, R. ruber, E. faecalis, and S. epidermidis.…”

Section: Scheme 64 Synthesis Of Amine-derived Bis-imidazoles 323a-i and Hydrochlorides 324a-dmentioning

confidence: 99%

“…The efficient and straightforward synthesis of these new quaternary salts was carried out by an approach in which a solution of 3 eq of 1H-imidazole (260) or 4-nitro-1H-imidazole (332) in a mixture of THF and DMF was treated with a suspension of 3.6 eq of NaH in THF and 1 eq of 2,6-bis(chloromethyl)pyridine (333) at room temperature. The resulting compounds 334a-g were then treated with a solution of 2.4-2.8 eq of α-halocarbonyl derivatives 335a-g giving rise to the required quaternary salts 331a-g in yields ranging from 50 to 92% (Scheme 67) [202]. 12), by using Pd(PPh3)4-catalysed Suzuki reactions followed by AcOH-mediated three component cyclisation reactions [203].…”

Section: Scheme 64 Synthesis Of Amine-derived Bis-imidazoles 323a-i and Hydrochlorides 324a-dmentioning

confidence: 99%

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An Updated Review on the Synthesis and Antibacterial Activity of Molecular Hybrids and Conjugates Bearing Imidazole Moiety

Rossi

Ciofalo

2020

Molecules

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The rapid growth of serious infections caused by antibiotic resistant bacteria, especially the nosocomial ESKAPE pathogens, has been acknowledged by Governments and scientists and is one of the world’s major health problems. Various strategies have been and are currently investigated and developed to reduce and/or delay the bacterial resistance. One of these strategies regards the design and development of antimicrobial hybrids and conjugates. This unprecedented critical review, in which our continuing interest in the synthesis and evaluation of the bioactivity of imidazole derivatives is testified, aims to summarise and comment on the results obtained from the end of the 1900s until February 2020 in studies conducted by numerous international research groups on the synthesis and evaluation of the antibacterial properties of imidazole-based molecular hybrids and conjugates in which the pharmacophoric constituents of these compounds are directly covalently linked or connected through a linker or spacer. In this review, significant attention was paid to summarise the strategies used to overcome the antibiotic resistance of pathogens whose infections are difficult to treat with conventional antibiotics. However, it does not include literature data on the synthesis and evaluation of the bioactivity of hybrids and conjugates in which an imidazole moiety is fused with a carbo- or heterocyclic subunit.

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Regioselective Synthesis of Novel [1,2,4]Triazolo[1,5‐a]pyridine Derivatives

et al. 2021

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Herein we report the reaction of 2‐(5‐aryl‐4H‐1,2,4‐triazol‐3‐yl)acetonitriles 1 a,b with appropriate Michael acceptors 2–4 to give novel [1,2,4]triazolo[1,5‐a]pyridines 5–8, whose antioxidant properties have been investigated. A plausible reaction mechanism, supported by DFT calculations, has been proposed to explain the total observed regioselective formation of [1,2,4]triazolo[1,5‐a]pyridine derivatives depending on the type of substituents on the Michael acceptor. Triazoles are well‐known agents exhibiting antimicrobial,[1] antitumor,[2] anti‐inflammatory,[3] antihypertensive,[4] anticonvulsant,[5] antiviral[6] and analgesic[7] biological activities. On the other hand, pyridine is the key core of heterocyclic derivatives showing a variety of pharmacological properties.[8–12] Several studies have revealed that a combination of different bioactive molecules, having different mechanisms of action, is a current strategy affording useful therapeutic agents.[13] This is the case of the [1,2,4]triazolo[1,5‐a] pyridine heterocyclic motif,[14] present in a number of bioactive compounds,[15] and largely used in materials chemistry.[16] Accordingly, diverse synthetic methods have been described for the synthesis of differently substituted [1,2,4]triazolo[1,5‐a]pyridines.[17–24] Our group has recently reported the ultrasound‐promoted facile and convenient “one‐pot” procedure for the synthesis of novel [1,2,4]triazolo[1,5‐a]pyridines in short reaction times and high yields, based on the reaction of 2‐(5‐aryl‐4H‐1,2,4‐triazol‐3‐yl)acetonitriles, malononitrile (or ethyl cyanoacetate) and aromatic aldehydes, in absolute ethanol, in the presence of IRA‐400.[25]

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Bis -(Imidazole/Benzimidazole)-Pyridine Derivatives: Synthesis, Structure and Antimycobacterial Activity

Cited by 39 publications

References 59 publications

Hybrid Quinoline-Sulfonamide Complexes (M2+) Derivatives with Antimicrobial Activity

Hybrid Quinoline-Sulfonamide Complexes (M2+) Derivatives with Antimicrobial Activity

An Updated Review on the Synthesis and Antibacterial Activity of Molecular Hybrids and Conjugates Bearing Imidazole Moiety

Regioselective Synthesis of Novel [1,2,4]Triazolo[1,5‐a]pyridine Derivatives

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