Synthesis and antimicrobial activity of some new 4-triazolylmethoxy-2H-chromen-2-one derivatives

Panda, Siva S.; Malik, Ritu; Chand, Mahesh; Jain, Subhash C.

doi:10.1007/s00044-011-9881-0

Cited by 19 publications

(8 citation statements)

References 13 publications

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“…A facile synthesis of the key intermediate hydrazide 20 involves the hydrazinolysis reaction of ester 19 and hydrazine hydrate in absolute ethanol at room temperature. Furthermore, the Schiff's base 21 was synthesized by the reaction of hydrazide intermediate 20 with 4‐fluorobenzaldehyde.…”

Section: Resultsmentioning

confidence: 99%

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New Coumarin Derivatives as Anti‐Breast and Anti‐Cervical Cancer Agents Targeting VEGFR‐2 and p38α MAPK

Batran

Dawood

Elseginy

et al. 2017

Archiv der Pharmazie

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Breast and cervical cancers are the most common gender-specific cancers affecting women worldwide. In this investigation, we highlighted the synthesis, VEGFR-2 and p38α MAPK inhibitory activity of new series of fluorinated coumarin-based derivatives featuring a variety of bioactive chemical moieties attached or fused to the coumarin nucleus at the 3 and/or 4 position. The bioactive inhibitors were further assessed for their anti-proliferative effect against human MCF-7 breast cancer and HeLa cervical cancer cell lines, respectively. Most of the tested compounds showed potent preferential inhibition effects against human VEGFR-2 and remarkable anticancer activities in the human breast cancer cell line MCF-7. Compounds 29, 24, and 2 displayed the highest inhibitory activity against VEGFR-2 (94% inhibition) and they were the most potent anticancer agents toward MCF-7 cancer cells with IC values of 7.90, 8.28, and 8.30 μg/mL, respectively. Compound 13 inhibited p38α MAPK phosphorylation with a significant reduction in % cell viability against HeLa cancer cells at 10 and 30 µM. Docking experiments carried out on VEGFR-2 and p38 MAPK crystallographic structures revealed that the active compounds bind to the active sites through H-bonds, arene-cation, and hydrophobic π-π interactions. QSAR analysis demonstrated considerable correlation coefficient (R = 0.76969) and root mean square error (RMSE = 0.10446) values. Also, the residual values between the experimental pIC and predicted pIC are very close, indicating the reliability of the established QSAR model.

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Section: Resultsmentioning

confidence: 99%

“…The purity of the newly synthesized compounds was assessed by TLC and elemental analysis and was found to be higher than 95%. Compounds 1 , 3 , 6 , 9 , 15 , 16 , 19 , 20 , 21 , and 23 were previously prepared and characterized.…”

Section: Methodsmentioning

confidence: 99%

New Coumarin Derivatives as Anti‐Breast and Anti‐Cervical Cancer Agents Targeting VEGFR‐2 and p38α MAPK

Batran

Dawood

Elseginy

et al. 2017

Archiv der Pharmazie

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“…The ether tethered coumarin–1,2,4‐triazole hybrids 8 (Fig. ) also exhibited promising antimicrobial activity with MIC of 6.25–50 μg/mL, and some of them were as active as the references CPFX and Miconazole . The SAR suggested that hybrids bearing furan and thiophene motif in 1,2,4‐triazole moiety displayed enhanced potency as compared with these with substituted phenyl groups generally.…”

Section: Antibacterial and Antifungal Activitiesmentioning

confidence: 95%

Coumarin–triazole Hybrids and Their Biological Activities

Fan

Xing

Liu

2018

Journal of Heterocyclic Chem

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Hybridization is emerged as a promising strategy in the discovery of new drugs, especially these with complimentary activities and multiple pharmacological targets that are the potential weapons to prevent the drug resistance. Currently, several hybrids are under different stages of clinical trial, and may be introduced into clinical practice to treat various diseases in the near future. Triazoles including 1,2,3‐triazole and 1,2,4‐triazole as well as coumarins occupy an important position in medicinal chemistry attribute to their various biological activities, and some of them have been used in clinical practice. Obviously, hybridization of these two pharmacophores may lead to novel candidates with broader spectrum, more effective, lower toxicity, and multiple mechanisms of action. This review aims to outline the biological activities of coumarin–triazole hybrids, and discuss their structure–activity relationship to pave the way for the further rational development of this kind of hybrids.

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“…The protons of -OCH 3 appeared as a singlet at δ 3.77 in its 1 H NMR and in 13 and DMSO was used for a blank. 33,34 The experiments were repeated three times and the average values are presented in Table 1. Figures 1 and 2 show the graphical representation.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and antimicrobial and antioxidant activities of hybrid molecules containing benzotriazole and 1,2,4-triazole

Chand¹,

Kaushik²,

Jain³

2018

Turk J Chem

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Eleven novel 1,2,4-triazolylbenzotriazoles have been prepared using 1-(hydrazinylcarbonylmethyl)-1 H-benzotriazole (3) as a potent intermediate. Compound 3, however, was obtained from benzotriazole in two steps. All synthesized compounds were characterized by detailed spectral studies like IR, 1 H NMR, 13 C NMR, and mass spectrometry. All synthesized compounds were evaluated for their in vitro antimicrobial activity against seven strains of bacteria and four strains of fungi. Compounds 13, 17, 19, 20, and 21 were found to possess antibacterial activity comparable to that of ciprofloxacin against a Klebsiella pneumoniae strain. Except for compounds 2 and 13, all compounds showed good antifungal activity against an Aspergillus niger strain as compared to miconazole. The synthesized compounds were also evaluated for their antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay and the results are encouraging, especially for compounds 3, 20, and 21.

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Synthesis and antimicrobial activity of some new 4-triazolylmethoxy-2H-chromen-2-one derivatives

Cited by 19 publications

References 13 publications

New Coumarin Derivatives as Anti‐Breast and Anti‐Cervical Cancer Agents Targeting VEGFR‐2 and p38α MAPK

New Coumarin Derivatives as Anti‐Breast and Anti‐Cervical Cancer Agents Targeting VEGFR‐2 and p38α MAPK

Coumarin–triazole Hybrids and Their Biological Activities

Synthesis and antimicrobial and antioxidant activities of hybrid molecules containing benzotriazole and 1,2,4-triazole

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