Synthesis and antibacterial activity screening of quaternary ammonium derivatives of triazolyl pyranochromenones

Yadav, Preeti; Kumar, Bipul; Gautam, Hemant K.; Sharma, Sunil K.

doi:10.1007/s12039-016-1214-x

Cited by 12 publications

(6 citation statements)

References 26 publications

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“…Long alkyl chain quaternary ammonium compounds (QACs) exert a broad range of antibacterial activity against Gram-positive and Gram-negative bacteria, some pathogenic species of fungi and protozoa. 15,16 The amphiphilic nature of QACs, are concurrently exploited for their surfactant, preserving and antimicrobial properties in some cosmetic and personal care products. 17,18 Structural aspects and a variety of biological activities of azo compounds and quaternary pyridinium salts were a motivation for the synthesis of five new azo compounds containing long chain alkyl pyridinium salts for the studies of antibacterial and antioxidant properties.…”

Section: * For Correspondencementioning

confidence: 99%

Synthesis, characterization, spectroscopy and biological activity of 4-((3-formyl-4-hydroxyphenyl)azo)-1-alkylpyridinium salts

et al. 2018

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The reaction of 2-hydroxy-5-(pyridine-4-yldiazenyl)benzaldehyde with n-alkyl bromides generated five novel azo pyridinium salts in good to excellent yields. The 1 H and 13 C NMR and UV-Vis absorption spectra indicated several tautomers for the new compounds. The NMR, UV-Vis absorption spectra and quantum chemical calculations show that the azo pyridinium salts have a new resonant structure compared to the corresponding azo precursor. Antibacterial activity was studied by disc diffusion and MIC methods. Diphenylpicrylhydrazyl (DPPH) assay was used to determine the antioxidant properties. The effects of carbon chain length on antimicrobial activity were also investigated. The results showed that existence of alkyl groups is crucial for the antibacterial properties. The new compound with decyl group displayed the best antibacterial activity. prepared and purified according to the method reported in the literature. 19 Melting points were measured on an Electrothermal 9200 apparatus. Mass spectra were recorded on an Agilent MS Model 5973. FT-IR spectra were recorded on a Shimadzu 8400S spectrometer using KBr disc. The electronic absorption spectra were recorded with a Shimadzu 1650 spectrophotometer. 1 H and 13 C NMR spectra were recorded in DMSO-d 6 as the solvent on the Bruker DRX-300 MHz and 400 MHz Advance spectrometers.

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Section: * For Correspondencementioning

confidence: 99%

Synthesis, characterization, spectroscopy and biological activity of 4-((3-formyl-4-hydroxyphenyl)azo)-1-alkylpyridinium salts

et al. 2018

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“…To seek for more effective antimicrobial agents, the effect of varying the substituent (R) as well as the length of the spacer (n) between the triazolyl coumarins and quaternary ammonium group on the antibacterial activity of coumarin–1,2,3‐triazole hybrids 6 has been evaluated by Sharma et al . The preliminary results suggested that both the length of spacer (n) and substituents (‐H /‐ OH /‐ OMe) resulted in the variation in the lipophilicity of the hybrids, and this in turn affect the antibacterial activity.…”

Section: Antibacterial and Antifungal Activitiesmentioning

confidence: 99%

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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“…2H-Chromen-2-one (coumarin) and its derivatives belong to a class of organic compounds possessing a wide range of biological activities (Penta, 2016;Kumar et al, 2018;Fan et al, 2018). Coumarin-triazole hybrids have attracted noticeable attention due to their antibacterial (Kusanur & Kulkarni, 2005;Shi & Zhou, 2011;Sarasija et al, 2012;Kushwaha et al, 2014;Dongamanti et al, 2014;Ferreira et al, 2015;Zayane et al, 2016;Yadav et al, 2017), antifungal (Feng et al, 2008;Kokil et al, 2010;Panda et al, 2012), antimycobacterial (Xu et al, 2017), anti-Alzheimer (Bagheri et al, 2015;Park et al, 2016;Montanari et al, 2016), anti-inflammatory (Sandhya et al, 2011;Stefani et al, 2012;Seerden et al, 2014) and antitumour (Maiti et al, 2013;Rehman et al, 2014;Zhang et al, 2014;Kraljević et al, 2016;Singh et al, 2017;Liu et al, 2017) activities.…”

Section: Introductionmentioning

confidence: 99%

Polymorphism of 3-(5-phenyl-1,3,4-oxadiazol-2-yl)- and 3-[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]-2H-chromen-2-ones

et al. 2019

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This study of 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one, C 17 H 10 N 2 O 3 , 1, and 3-[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]-2H-chromen-2-one, C 16 H 9 N 3 O 3 , 2, was performed on the assumption of the potential anticancer activity of the compounds. Three polymorphic structures for 1 and two polymorphic structures for 2 have been studied thoroughly. The strongest intermolecular interaction is stacking of the 'head-to-head' type in all the studied crystals. The polymorphic structures of 1 differ with respect to the intermolecular interactions between stacked columns. Two of the polymorphs have a columnar or double columnar type of crystal organization, while the third polymorphic structure can be classified as columnar-layered. The difference between the two structures of 2 is less pronounced. Both crystals can be considered as having very similar arrangements of neighbouring columns. The formation of polymorphic modifications is caused by a subtle balance of very weak intermolecular interactions and packing differences can be identified only using an analysis based on a study of the pairwise interaction energies.

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Synthesis and antibacterial activity screening of quaternary ammonium derivatives of triazolyl pyranochromenones

Cited by 12 publications

References 26 publications

Synthesis, characterization, spectroscopy and biological activity of 4-((3-formyl-4-hydroxyphenyl)azo)-1-alkylpyridinium salts

Synthesis, characterization, spectroscopy and biological activity of 4-((3-formyl-4-hydroxyphenyl)azo)-1-alkylpyridinium salts

Coumarin–triazole Hybrids and Their Biological Activities

Polymorphism of 3-(5-phenyl-1,3,4-oxadiazol-2-yl)- and 3-[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]-2H-chromen-2-ones

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