Novel coumarin-pyrazole carboxamide derivatives as potential topoisomerase II inhibitors: Design, synthesis and antibacterial activity

Liu, Hao; Ren, Zi-Li; Wang, Wei; Gong, Jie-Xiu; Chu, Ming-Jie; Ma, Quan-Wei; Wang, Jie-Chun; Lv, Xian-Hai

doi:10.1016/j.ejmech.2018.07.059

Cited by 76 publications

(34 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…6 ,7 -Dihydroxybergamottin was the most active against all the bacteria strains tested, probably because of the aliphatic chain in C5 position; similar activity was noticed for peucedanin and officinalin isobutyrate. Liu and colleagues made a huge effort to synthesize and identify coumarin-pyrazole carboxamide derivatives as potential topoisomerase-II inhibitors: 70 novel compounds were obtained and evaluated [87].…”

Section: ) Andmentioning

confidence: 99%

“…Coumarin derivatives are endowed with antifungal activity, potentially useful in both pharma and agri-food sectors. In this Liu and colleagues made a huge effort to synthesize and identify coumarin-pyrazole carboxamide derivatives as potential topoisomerase-II inhibitors: 70 novel compounds were obtained and evaluated [87].…”

Section: Antifungal Activitymentioning

confidence: 99%

“…The selected compounds exhibited also potent inhibition against Topo II and Topo IV with IC 50 values in the range 9.4-25 mg/L. Liu and colleagues made a huge effort to synthesize and identify coumarin-pyrazole carboxamide derivatives as potential topoisomerase-II inhibitors: 70 novel compounds were obtained and evaluated [87].…”

Section: Antifungal Activitymentioning

confidence: 99%

See 2 more Smart Citations

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Annunziata

Pinna

Dallavalle

et al. 2020

IJMS

280

156

View full text Add to dashboard Cite

Privileged structures have been widely used as an effective template for the research and discovery of high value chemicals. Coumarin is a simple scaffold widespread in Nature and it can be found in a considerable number of plants as well as in some fungi and bacteria. In the last years, these natural compounds have been gaining an increasing attention from the scientific community for their wide range of biological activities, mainly due to their ability to interact with diverse enzymes and receptors in living organisms. In addition, coumarin nucleus has proved to be easily synthetized and decorated, giving the possibility of designing new coumarin-based compounds and investigating their potential in the treatment of various diseases. The versatility of coumarin scaffold finds applications not only in medicinal chemistry but also in the agrochemical field as well as in the cosmetic and fragrances industry. This review is intended to be a critical overview on coumarins, comprehensive of natural sources, metabolites, biological evaluations and synthetic approaches.

show abstract

Section: ) Andmentioning

confidence: 99%

Section: Antifungal Activitymentioning

confidence: 99%

See 1 more Smart Citation

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Annunziata

Pinna

Dallavalle

et al. 2020

IJMS

280

156

View full text Add to dashboard Cite

show abstract

“…Many authors have published researches exploring the medicinal properties of coumarins [4,6,12,[35][36][37]. Coumarins possess antimicrobial activity such as antibacterial [38][39][40][41][42][43][44] and antifungal [40,[45][46][47][48]. Numerous coumarin derivatives showed significant antioxidant activity [49][50][51][52][53].…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Synthesis of Coumarin Derivatives from Different Starting Materials

et al. 2020

View full text Add to dashboard Cite

The study of coumarin dates back to 1820 when coumarin was first extracted from tonka bean by Vogel. Compounds containing coumarin backbone are a very important group of compounds due to their usage in pharmacy and medicine. Properties and biological activities of coumarin derivatives have a significant role in the development of new drugs. Therefore, many different methods and techniques are developed in order to synthesize coumarin derivatives. Coumarin derivatives could be obtained from different starting materials with various methods but with big differences in yield. This review summarized various methods, techniques and reaction conditions for synthesis of coumarins from different compounds such as aldehydes, phenols, ketones and carboxylic acids.

show abstract

“…Pyrazole derivatives play an imperative role in wide spectrum of biological activities including antibacterial 11 , antifungal 12 , antiinflammatory [13][14][15] , analgesic 16 , oestrogen receptor binding 17 , neuroprotective 18 , antineoplastic agents 19 . Furthermore, several reports exhibited that pyrazoles I-IV and pyrazolo [3,4- (Figure 1) had high bactericidal and fungicidal activity against the reference strains [20][21][22][23][24] . Additionally, the pyrazole-containing cores (VI-VII) were found to be active as antimicrobial and antimalarial through inhibition of DHFR [25][26][27] (Figure 2).…”

Section: Introductionmentioning

confidence: 99%

Novel heterocyclic hybrids of pyrazole targeting dihydrofolate reductase: design, biological evaluation and in silico studies

Othman

Gad‐Elkareem

Amr

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

View full text Add to dashboard Cite

A novel series of pyrazole analogues including hydrazones, pyrazolo[4,3-c]-pyridazines, pyrazolo[3,4e][1,2,4]triazine and pyrazolo[3,4-d][1,2,3]triazoles was designed, synthesised and screened for their in vitro antimicrobial and DHFR inhibition activity. Compounds bearing benzenesulphonamide moiety incorporated with 3-methyl-5-oxo-1H-pyrazol-4(5H)-ylidene) hydrazine 3a or 6-amino-7-cyano-3-methyl-5H-pyrazolo[4,3-c]pyridazine 6a revealed excellent and broad spectrum antimicrobial activity comparable to ciprofloxacin and amphotericin B as positive antibiotic and antifungal controls, respectively. Furthermore, these derivatives proved to be the most active DHFR inhibitors with IC 50 values 0.11 ± 1.05 and 0.09 ± 0.91 mM, in comparison with methotrexate (IC 50 ¼ 0.14 ± 1.25 mM). The in silico studies were done to calculate the drug-likeness and toxicity risk parameters of the newly synthesised derivatives. Additionally, the high potency of the pyrazole derivatives bearing sulphonamide against DHFR was confirmed with molecular docking and might be used as an optimum lead for further modification.

show abstract

Novel coumarin-pyrazole carboxamide derivatives as potential topoisomerase II inhibitors: Design, synthesis and antibacterial activity

Cited by 76 publications

References 32 publications

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Recent Advances in the Synthesis of Coumarin Derivatives from Different Starting Materials

Novel heterocyclic hybrids of pyrazole targeting dihydrofolate reductase: design, biological evaluation and in silico studies

Contact Info

Product

Resources

About