Synthesis and biologic activities of some novel heterocyclic chalcone derivatives

Sharma, Punita; Kumar, Suresh; Ali, Furqan; Anthal, Sumati; Gupta, Vivek K.; Khan, Inshad Ali; Singh, Surjeet; Sangwan, Payare L.; Suri, K. A.; Gupta, B. D.; Gupta, D. K.; Dutt, Prabhu; Vishwakarma, Ram A.; Satti, Naresh K.

doi:10.1007/s00044-012-0401-7

Cited by 29 publications

(32 citation statements)

References 31 publications

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“…Inspired by the structural similarities with the coumaroyl substituents, a series of chalcones were tested as NorA inhibitors. Among them, compounds 45 and 46 (Figure ) decreased the MIC of ciprofloxacin against SA1199B with MPC 4 s of 8.1 and 51.8 µM, respectively . SARs revealed that (i) on ring A of the chalcone scaffold (Figure ), a favorable substituent for synergistic activity is methoxy at C2, while an additional methoxy at either C3, C4, or C5 does not affect the activity; (ii) on ring B of the chalcone scaffold (Figure ), a favorable substituent for synergistic activity is dimethylaminoethoxy at C4, while OH at this position leads to a loss of inhibitory activity.…”

Section: Efflux Pump Inhibitors Of Selected Clinically Relevant Pathosupporting

confidence: 89%

“…Among them, compounds 45 and 46 (Figure 11) decreased the MIC of ciprofloxacin against SA1199B with MPC 4 s of 8.1 and 51.8 µM, respectively. 212,213 SARs revealed that (i) on ring A of the chalcone scaffold ( Figure 11), a favorable substituent for synergistic activity is methoxy at C2, while an additional methoxy at either C3, C4, or C5 does not affect the activity; (ii) on ring B of the chalcone scaffold ( Figure 11), a favorable substituent for synergistic activity is dimethylaminoethoxy at C4, while OH at this position leads to a loss of inhibitory activity. The latter supports the hypothesis of Guz et al, 214 who have investigated the SAR of several flavolignans and flavones with NorA affinity.…”

Section: Flavones and Chalconesmentioning

confidence: 99%

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Efflux pump inhibitors of clinically relevant multidrug resistant bacteria

Lamut

Mašič

Kikelj

et al. 2019

Medicinal Research Reviews

145

116

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Bacterial infections are an increasingly serious issue worldwide. The inability of existing therapies to treat multidrug‐resistant pathogens has been recognized as an important challenge of the 21st century. Efflux pumps are important in both intrinsic and acquired bacterial resistance and identification of small molecule efflux pump inhibitors (EPIs), capable of restoring the effectiveness of available antibiotics, is an active research field. In the last two decades, much effort has been made to identify novel EPIs. However, none of them has so far been approved for therapeutic use. In this article, we explore different structural families of currently known EPIs for multidrug resistance efflux systems in the most extensively studied pathogens (NorA in Staphylococcus aureus, AcrAB‐TolC in Escherichia coli, and MexAB‐OprM in Pseudomonas aeruginosa). Both synthetic and natural compounds are described, with structure‐activity relationship studies and optimization processes presented systematically for each family individually. In vitro activities against selected test strains are presented in a unifying manner for all the EPIs described, together with the most important toxicity, pharmacokinetic and in vivo efficacy data. A critical evaluation of lead‐likeness characteristics and the potential for clinical development of the most promising inhibitors of the three efflux systems is described. This overview of EPIs is a good starting point for the identification of novel effective antibacterial drugs.

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Section: Efflux Pump Inhibitors Of Selected Clinically Relevant Pathosupporting

confidence: 89%

Section: Flavones and Chalconesmentioning

confidence: 99%

Efflux pump inhibitors of clinically relevant multidrug resistant bacteria

Lamut

Mašič

Kikelj

et al. 2019

Medicinal Research Reviews

145

116

View full text Add to dashboard Cite

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“…The Claisen-Schmidt condensation reaction between substituted acetophenones and aryl aldehydes under basic conditions has been widely used to synthesize chalcone derivatives (Ghosh & Das, 2014;Robinson et al, 2013;Sharma et al, 2013;Tiwari et al, 2010). Chalcones, belonging to the flavonoid family, are an important class of natural products with widespread distribution in fruits, vegetables, spices and tea.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of the chalcone (E)-3-(furan-2-yl)-1-phenylprop-2-en-1-one

Vázquez‐Vuelvas

Enríquez‐Figueroa

García-Ortega

et al. 2015

Acta Crystallogr E Cryst Commun

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“…Chalcones are a significant constituent of natural products which indicates a broad range of biological properties such as anti‐inflammatory, anti‐oxidant and anti‐tumor activity …”

Section: 4‐disubstituted‐123‐triazoles As Anti‐cancer Agentsmentioning

confidence: 99%

An Overview of Recent Advances in the Applications of Click Chemistry in the Synthesis of Bioconjugates with Anticancer Activities

Mashayekh

Shiri

2019

ChemistrySelect

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The click chemistry is one of the most powerful CÀ N bond forming-reactions towards five-membered heterocycles. The copper-catalyzed azide-alkyne cycloaddition (CuAAC) has widely used in the discovery of anti-cancer drugs and many articles have been published in this field. This review article aims to review general mechanism aspects and the recent advances (2016-2019) of click chemistry for cancer therapy.

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Synthesis and biologic activities of some novel heterocyclic chalcone derivatives

Cited by 29 publications

References 31 publications

Efflux pump inhibitors of clinically relevant multidrug resistant bacteria

Efflux pump inhibitors of clinically relevant multidrug resistant bacteria

Crystal structure of the chalcone (E)-3-(furan-2-yl)-1-phenylprop-2-en-1-one

An Overview of Recent Advances in the Applications of Click Chemistry in the Synthesis of Bioconjugates with Anticancer Activities

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