Synthesis of bioactive and fluorescent pyridine-triazole-coumarin peptidomimetics through sequential click-multicomponent reactions

Soumya, T.; Ajmal, C. Muhammed; Bahulayan, D.

doi:10.1016/j.bmcl.2016.12.044

Cited by 21 publications

(15 citation statements)

References 43 publications

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“…[15,20,21] Moreover, 1,2,3-triazoles have become increasingly useful and important in the construction of bioactive and functional molecules as attractive linker units that could connect two pharmacophores to provide innovative bifunctional drugs. [22][23][24] Many drugs available in the market contain 1,2,3-triazole core in their structure, such as cefatrizine (antibiotic), carboxyamidotriazole (anticancer agent), rufinamide (anticonvulsant) and tazobactam (antibacterial agent; Figure 2).…”

Section: Diversely Functionalized 123-triazole Derivatives Have Attmentioning

confidence: 99%

New N‐phenylacetamide‐linked 1,2,3‐triazole‐tethered coumarin conjugates: Synthesis, bioevaluation, and molecular docking study

Akolkar

Nagargoje

Shaikh

et al. 2020

Archiv der Pharmazie

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A series of new 1,2,3-triazole-tethered coumarin conjugates linked by N-phenylacetamide was efficiently synthesized via the click chemistry approach in excellent yields. The synthesized conjugates were evaluated for their in vitro antifungal and antioxidant activities. Antifungal activity determination was carried out against fungal strains such as Candida albicans, Fusarium oxysporum, Aspergillus flavus, Aspergillus niger and Cryptococcus neoformans. Compounds 7b, 7d, 7e, 8b and 8e displayed higher potency than the standard drug miconazole, with lower minimum inhibitory concentration values. Also, compound 7a exhibited potential radical scavenging activity as compared with the standard antioxidant butylated hydroxytoluene. In addition, a molecular docking study of the newly synthesized compounds was carried out, and the results showed a good binding mode at the active site of the fungal (C. albicans) P450 cytochrome lanosterol 14α-demethylase enzyme. Furthermore, the synthesized compounds were also tested for ADME properties, and they demonstrated potential as good candidates for oral drugs.

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Section: Diversely Functionalized 123-triazole Derivatives Have Attmentioning

confidence: 99%

New N‐phenylacetamide‐linked 1,2,3‐triazole‐tethered coumarin conjugates: Synthesis, bioevaluation, and molecular docking study

Akolkar

Nagargoje

Shaikh

et al. 2020

Archiv der Pharmazie

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“…Various hydrazone 34 , [1,2,4‐triazolo][3,4‐ b ]thiadiazinyl 35 , pyrazole 36 , alkyl and aryl 37 , pyridine 38 , chalcone 39 , 3‐oxo‐2,3‐dihydrofuran 40 , pyrrole , dithiocarbamate , benzimidazole , dialkynylcarbinol , steroidal , costunolide , colchicines , (−)‐Dibromophakellstatin fused coumarin–triazole hybrids and cyclized coumarin–triazole hybrids , the 1,2,4‐triazole‐5‐one hybrids 41 , as well as triazole tethered bis‐coumarin 42 (Fig. ) were screened for their anticancer activities, in spite of the majority of them showed weak to moderate activity against the tested cancer cell lines, the enriched SAR paved the way to the further rational design.…”

Section: Antitumor Activitymentioning

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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“…Recently, outlook of multi‐component synthesis, particularly in heterocyclic chemistry, has taken a significant role for the developing photophysical properties of coumarin compounds . This approach is an effective tool in obtaining the desired variety of products.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and solvent‐dependent photophysics of a novel fluorescent triazole‐coumarin‐based dye

Kaya

Menteşe

2020

Journal of Heterocyclic Chem

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Synthesis of a new coumarin‐triazole‐based dye and its photophysical parameters such as absorption, fluorescence emission, and fluorescence quantum yield were investigated. Studies have shown that the present dye has symmetry with a mirror image, especially in the ethanol solvent, with respect to the absorption and fluorescence spectra. As a result of the UV‐vis and fluorescence spectroscopy techniques used, it was determined that absorption and emission spectra were shifted to the red with increasing solvent polarity. In addition, the spectral data of the synthesized compound exhibited that the stokes shifts are small, usually less than 50 nm, and the quantum yields are significantly high. In accordance with the results obtained, it can be stated that this novel dye synthesized here can offer an insight into application in sensor applications as analytical or biosensors, optoelectronic devices, and medicine industry.

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Synthesis of bioactive and fluorescent pyridine-triazole-coumarin peptidomimetics through sequential click-multicomponent reactions

Cited by 21 publications

References 43 publications

New N‐phenylacetamide‐linked 1,2,3‐triazole‐tethered coumarin conjugates: Synthesis, bioevaluation, and molecular docking study

New N‐phenylacetamide‐linked 1,2,3‐triazole‐tethered coumarin conjugates: Synthesis, bioevaluation, and molecular docking study

Coumarin–triazole Hybrids and Their Biological Activities

Synthesis and solvent‐dependent photophysics of a novel fluorescent triazole‐coumarin‐based dye

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