1,2,4-Triazole-quinoline/quinolone hybrids as potential anti-bacterial agents

Zhang, Jingyu; Wang, Su; Ba, Yanyan; Xu, Zhi

doi:10.1016/j.ejmech.2019.04.033

Cited by 94 publications

(49 citation statements)

References 69 publications

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“…The antifungal activity was based on targeting CYP53A15, a unique fungal enzyme known to play a role in demethyling lanosterol, subsequently promoting fungal growth [23]. Derivatives (3)(4)(5)(6)(7)(8)(9) (Figure 3) inhibited CYP53A15 enzymatic activity against the three fungi (Cochliobolus lunatus, Aspergillus niger and Pleurotus ostreatus) thereby revealing the potential antifungal activity of cinnamic acid derivatives [22]. Korosec et al tested antifungal activity of cinnamic acid derivatives, most of them were synthesized [22].…”

Section: Cinnamic Acid Derivatives With Antimicrobial Activitymentioning

confidence: 99%

“…Table 1. Comparing percentage fungal growth of the three fungi when treated with 0.5 mmol/L of cinnamic acid derivatives (3)(4)(5)(6)(7)(8)(9) [22].…”

Section: Cinnamic Acid Derivatives With Antimicrobial Activitymentioning

confidence: 99%

“…Cinnamic acid can be prepared by enzymatic deamination of phenylalanine [8]. Besides the cinnamic acid derivatives that occur naturally in plants [2], the presence of a benzene ring and the acrylic acid group makes it possible to modify it resulting in synthetic cinnamic acid derivatives [9]. Apart from them being intermediates in producing other compounds like stilbenes Besides the cinnamic acid derivatives that occur naturally in plants [2], the presence of a benzene ring and the acrylic acid group makes it possible to modify it resulting in synthetic cinnamic acid derivatives [9].…”

Section: Introductionmentioning

confidence: 99%

“…Besides the cinnamic acid derivatives that occur naturally in plants [2], the presence of a benzene ring and the acrylic acid group makes it possible to modify it resulting in synthetic cinnamic acid derivatives [9]. Apart from them being intermediates in producing other compounds like stilbenes Besides the cinnamic acid derivatives that occur naturally in plants [2], the presence of a benzene ring and the acrylic acid group makes it possible to modify it resulting in synthetic cinnamic acid derivatives [9]. Apart from them being intermediates in producing other compounds like stilbenes and styrenes, cinnamic acid derivatives exhibit antibacterial, antifungal, anti-inflammatory [10], neuroprotective [11], anticancer [12] and antidiabetic activities [13].…”

Section: Introductionmentioning

confidence: 99%

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Cinnamic Acid Derivatives and Their Biological Efficacy

Ruwizhi

Aderibigbe

2020

IJMS

211

134

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The role played by cinnamic acid derivatives in treating cancer, bacterial infections, diabetes and neurological disorders, among many, has been reported. Cinnamic acid is obtained from cinnamon bark. Its structure is composed of a benzene ring, an alkene double bond and an acrylic acid functional group making it possible to modify the aforementioned functionalities with a variety of compounds resulting in bioactive agents with enhanced efficacy. The nature of the substituents incorporated into cinnamic acid has been found to play a huge role in either enhancing or decreasing the biological efficacy of the synthesized cinnamic acid derivatives. Some of the derivatives have been reported to be more effective when compared to the standard drugs used to treat chronic or infectious diseases in vitro, thus making them very promising therapeutic agents. Compound 20 displayed potent anti-TB activity, compound 27 exhibited significant antibacterial activity on S. aureus strain of bacteria and compounds with potent antimalarial activity are 35a, 35g, 35i, 36i, and 36b. Furthermore, compounds 43d, 44o, 55g–55p, 59e, 59g displayed potent anticancer activity and compounds 86f–h were active against both hAChE and hBuChE. This review will expound on the recent advances on cinnamic acid derivatives and their biological efficacy.

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Section: Cinnamic Acid Derivatives With Antimicrobial Activitymentioning

confidence: 99%

“…Table 1. Comparing percentage fungal growth of the three fungi when treated with 0.5 mmol/L of cinnamic acid derivatives (3)(4)(5)(6)(7)(8)(9) [22].…”

Section: Cinnamic Acid Derivatives With Antimicrobial Activitymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Cinnamic Acid Derivatives and Their Biological Efficacy

Ruwizhi

Aderibigbe

2020

IJMS

211

134

View full text Add to dashboard Cite

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“…In recent years, the trend in reducing infectious disease mortality has been threatened by the emergence of strains of bacteria that are no longer susceptible to the currently available antimicrobial agents such as the Gram-negative Acinetobacter baumannii, Pseudomonas aeruginosa, or the Gram-positive Enterococcus faecium, or Staphylococcus aureus added to the multi-and extensivelydrug-resistant Mycobacterium tuberculosis. Regarding fungi, they are also a source of concern in antifungal chemotherapy because many fungi can be opportunistic pathogens seriously affecting the synthesis of molecular hybrids containing two or more covalently joined antimicrobial pharmacophores within a single molecule [3][4][5].…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium Hybrids

et al. 2019

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Eight quinoline-based hydroxyimidazolium hybrids 7a–h were prepared and evaluated in vitro against a panel of clinically important fungal and bacterial pathogens, including mycobacteria. Hybrid compounds 7c–d showed remarkable antifungal activity against Cryptococcus neoformans with a minimum inhibitory concentration (MIC) value of 15.6 µg/mL. Against other opportunistic fungi such as Candida spp. and Aspergillus spp., these hybrids showed MIC values of 62.5 µg/mL. Regarding their antibacterial activity, all the synthetic hybrids demonstrated little inhibition of Gram-negative bacteria (MIC ≥50 µg/mL), however, hybrid 7b displayed >50% inhibition against Klebsiella pneumoniae at 20 µg/mL and full inhibition at 50 µg/mL. Moreover, this hybrid was shown to be a potent anti-staphylococcal molecule, with a MIC value of 2 µg/mL (5 µM). In addition, hybrid 7h also demonstrated inhibition of Staphylococcus aureus at 20 µg/mL (47 µM). Hybrids 7a and 7b were the most potent against Mycobacterium tuberculosis H37Rv with MIC values of 20 and 10 µg/mL (46 and 24 µM), respectively. The 7b hybrid demonstrated high selectivity in killing S. aureus and M. tuberculosis H37Rv in comparison with mammalian cells (SI >20), and thus it can be considered a hit molecule for mechanism of action studies and the exploration of related chemical space.

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Sequential Organocatalytic Synthesis of [1,2,3]Triazolo[1,5‐a]quinolines

et al. 2020

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In this work, a one-pot sequential organocatalytic method for the synthesis of fused [1,2,3]triazolo [1,5-a]quinolines through successive cyclization and condensation is presented. In this synthetic strategy, the intermolecular [3 + 2]-cycloaddition occurs between 1,3-dicarbonyl compounds and o-carbonyl-substituted phenylazide compounds, for the formation of the 1,2,3-triazole intermediates. Subsequently, an intramolecular condensation reaction generates the fused quinoline ring by the new CÀ C bond formation, giving the products in yields ranging from moderate to excellent. All the reactions were performed using 20 mol% of 1,8diazabicyclo[5.4.0]undec-7-ene (DBU) as catalyst in the presence of DMSO as solvent at 120°C for 24 h and tolerate a range of 1,3-dicarbonyl compounds, such as β-keto esters and 1,3-diketones, and o-formyl, o-acetyl or o-benzoyl substituted phenylazide compounds.

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1,2,4-Triazole-quinoline/quinolone hybrids as potential anti-bacterial agents

Cited by 94 publications

References 69 publications

Cinnamic Acid Derivatives and Their Biological Efficacy

Cinnamic Acid Derivatives and Their Biological Efficacy

Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium Hybrids

Sequential Organocatalytic Synthesis of [1,2,3]Triazolo[1,5‐a]quinolines

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