New amide linked dimeric 1,2,3-triazoles bearing aryloxy scaffolds as a potent antiproliferative agents and EGFR tyrosine kinase phosphorylation inhibitors

Deshmukh, Tejshri R.; Sarkate, Aniket P.; Lokwani, Deepak K.; Tiwari, Shailee V.; Azad, Rajaram; Shingate, Bapurao B.

doi:10.1016/j.bmcl.2019.08.022

Cited by 23 publications

(13 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In continuation of our previous works [40,[42][43][44][45][46][47][48][49][50][51] on the synthesis and biological evaluation of heterocycles, and the significance of coumarin and 1,2,3-triazole moieties in a single molecular framework, herein, we would like to report the design and syntheses of new N-phenylacetamide-linked coumarin-triazole conjugates by using the molecular hybridization approach ( Figure 3). several biological activities.…”

Section: Synthesis Of New Heterocycles With Multiple Biological Activmentioning

confidence: 91%

“…several biological activities. [52][53][54][55] On the basis of these reports and The starting materials, 2-azido-N-phenylacetamides 3a-g, were prepared by a previously reported method [45,51] from corresponding anilines in excellent yields (Scheme 1). The 7-hydroxy-4-methyl coumarin 5a has been synthesized via acid-catalyzed Pechmann condensation between resorcinol and ethyl acetoacetate in 80% yield (Scheme 1).…”

Section: Synthesis Of New Heterocycles With Multiple Biological Activmentioning

confidence: 99%

See 1 more Smart Citation

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

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Section: Synthesis Of New Heterocycles With Multiple Biological Activmentioning

confidence: 91%

Section: Synthesis Of New Heterocycles With Multiple Biological Activmentioning

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

Self Cite

View full text Add to dashboard Cite

show abstract

“…MW [a] QPlogPo/w [b] QPlogS [c] PSA [d] QPPMDCK [e] Percent Human Oral Absorption [f] cMet [a] Molecular weight of the molecule, [b] Predicted octanol/water partition co-efficient log P (acceptable range: À 2.0 to 6.5). [25][26][27][28][29] , [c] Predicted aqueous solubility; S in mol/L (acceptable range: À 6.5 to 0.5). [25][26][27][28][29] , [d] PSA (Polar surface area) (acceptable range: 7.0 to 200.0).…”

Section: Generation Of Qsar Modelsmentioning

confidence: 99%

“…[25][26][27][28][29] , [c] Predicted aqueous solubility; S in mol/L (acceptable range: À 6.5 to 0.5). [25][26][27][28][29] , [d] PSA (Polar surface area) (acceptable range: 7.0 to 200.0). [25][26][27][28][29] , [e] Predicted apparent MDCK cell permeability in nm/sec (acceptable range: > 500 is high, < 25 is poor).…”

Section: Generation Of Qsar Modelsmentioning

confidence: 99%

See 1 more Smart Citation

Auto QSAR‐ A Fast Approach for Creation and Application of QSAR Models through Automation

2020

Self Cite

View full text Add to dashboard Cite

A continuous and undefined malignant growth in cancer makes it an extremely heterogeneous complex disease. Different types of enzymes helps in detection of cancerous growth in the human body. In this work, different predictive Quantitative Structure‐Activity Relationship (QSAR) models by means of various molecular modeling techniques using 43 novel 6, 7‐disubstituted‐4‐phenoxyquinoline derivatives acting as Tyrosine‐protein kinase Met or hepatocyte growth factor receptor (HGFR) (c‐Met kinase) inhibitors were designed. Best QSAR models were generated through Auto QSAR. Predicted activity of these models was compared with the observed activity from literature, and it was observed that potent compound 18 b gave high docking results. Auto‐QSAR technique provided the perfect model for the designed derivatives. Binding affinity of compounds for c‐Met kinase enzyme was studied by molecular docking and Molecular Mechanics/Generalized Born Surface Area (MM/GBSA dG) binding studies. Optimized compounds were subjected to in silico ADMET studies for predicting drug‐likeliness and toxicity properties. Reported work will assist to design, refine and construct the novel phenoxyquinoline derivatives as potent c‐Met kinase inhibitors in near future.

show abstract

[Et₃NH][HSO₄] catalyzed solvent‐free synthesis of new 1,2,3‐triazolidene‐indolinone derivatives

Siddiqui

Nagargoje

Raza

et al. 2022

Journal of Heterocyclic Chem

Self Cite

View full text Add to dashboard Cite

A series of new 1,2,3‐triazolidene‐indolinone derivatives (17a‐j) were designed and synthesized via [Et3NH] [HSO4] catalyzed solvent‐free approach. The synthesis strongly relied on Knoevenagel condensation of 1,4‐disubstituted 1,2,3‐triazolyl aldehydes (15a‐j) and oxindole (5). The solvent‐free approach and Brønsted acidity of [Et3NH] [HSO4] ionic liquid increased the rate of reaction and provided the corresponding 1,2,3‐triazolidene‐indolinone derivatives (17a‐j) in excellent yields. The reusability of ionic liquid is also established with persistent effective yields up to four cycles. These novel 1,2,3‐triazolidene‐indolinone derivatives may exhibit potential biological response due to the presence of potent moieties and presence of triazolidene‐exocyclic double bond.

show abstract

New amide linked dimeric 1,2,3-triazoles bearing aryloxy scaffolds as a potent antiproliferative agents and EGFR tyrosine kinase phosphorylation inhibitors

Cited by 23 publications

References 24 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

Auto QSAR‐ A Fast Approach for Creation and Application of QSAR Models through Automation

[Et₃NH][HSO₄] catalyzed solvent‐free synthesis of new 1,2,3‐triazolidene‐indolinone derivatives

Contact Info

Product

Resources

About

New amide linked dimeric 1,2,3-triazoles bearing aryloxy scaffolds as a potent antiproliferative agents and EGFR tyrosine kinase phosphorylation inhibitors

Cited by 23 publications

References 24 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

Auto QSAR‐ A Fast Approach for Creation and Application of QSAR Models through Automation

[Et3NH][HSO4] catalyzed solvent‐free synthesis of new 1,2,3‐triazolidene‐indolinone derivatives

Contact Info

Product

Resources

About

[Et₃NH][HSO₄] catalyzed solvent‐free synthesis of new 1,2,3‐triazolidene‐indolinone derivatives