scholarly journals Synthesis, ADMET and Docking Studies of Novel Pyrazoles Incorporating Coumarin Moiety as Tyrosine Kinase (Src) Inhibitors

2021 ◽  
Vol 11 (5) ◽  
pp. 13706-13714
Keyword(s):  
Tyrosine Kinase ◽  
Mass Spectra ◽  
Kinase Inhibitors ◽  
Cycloaddition Reaction ◽  
Docking Studies ◽  
Dipolar Cycloaddition ◽  
Inhibition Activity ◽  
Spectral Techniques ◽  
Chemical Structures

Novel pyrazoles incorporating coumarin moiety have been synthesized by the 1,3-dipolar cycloaddition reaction of the nitrilimines that were generated in situ from hydrazonyl halides by the action of triethylamine and the enaminone named E-3-(3-(dimethylamino)acryloyl)-8-methoxy-2H-chromen-2-one (1) in dry benzene for 6 h. These novel compounds' chemical structures were elucidated by physical and spectral techniques, including FTIR, 1H-NMR, 13C-NMR, 1H-13C HMBC NMR, and mass spectra. These molecules were predicted to show tyrosine kinase inhibition activity, which was further validated by docking studies. These molecules also showed good ADMET properties and passed Lipinski’s filters for drug-likeness. These results collectively paved the way for developing pyrazoles incorporating coumarin moiety as possible tyrosine kinase inhibitors.

scholarly journals Green ultrasound-assisted three-component click synthesis of novel 1H-1,2,3-triazole carrying benzothiazoles and fluorinated-1,2,4-triazole conjugates and their antimicrobial evaluation

2017 ◽  
Vol 67 (3) ◽  
pp. 309-324 ◽  
Author(s):  
Nadjet Rezki ◽  
Mohamed Reda Aouad
Keyword(s):  
Antimicrobial Activity ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Terminal Alkynes ◽  
One Pot ◽  
Alkyl Aryl ◽  
Antimicrobial Evaluation ◽  
Ultrasound Assisted ◽  
Click Synthesis

AbstractThe present study describes an efficient and ecofriendly, ultrasound, one-pot click cycloaddition approach for the construction of a novel series of 1,4-disubstituted-1,2,3-triazoles tethered with fluorinated 1,2,4-triazole-benzothiazole molecular conjugates. It involved three-component condensation of the appropriate bromoacetamide benzothiazole, sodium azide and 4-alkyl/aryl-5-(2-fluorophenyl)-3-(prop-2-ynylthio)-1,2,4-triazoles4a-ethrough a Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction. This approach involvesin situgeneration of azidoacetamide benzothiazole, followed by condensation with terminal alkynes in the presence of CuSO4/Na-ascorbate in aqueous DMSO under both conventional and ultrasound conditions. Some of the designed 1,2,3-triazole conjugates6a-owere recognized for their antimicrobial activity against some bacterial and fungal pathogenic strains.

scholarly journals (Phenylamino)pyrimidine-1,2,3-triazole derivatives as analogs of imatinib: searching for novel compounds against chronic myeloid leukemia

2021 ◽  
Vol 17 ◽  
pp. 2260-2269
Author(s):  
Luiz Claudio Ferreira Pimentel ◽  
Lucas Villas Boas Hoelz ◽  
Henayle Fernandes Canzian ◽  
Frederico Silva Castelo Branco ◽  
Andressa Paula de Oliveira ◽  
...  
Keyword(s):  
Chronic Myeloid Leukemia ◽  
Tyrosine Kinase ◽  
Myeloid Leukemia ◽  
Kinase Inhibitors ◽  
Competitive Inhibition ◽  
Leukemia Cell ◽  
Docking Studies ◽  
Leukemia Cell Line ◽  
Inhibition Mechanism ◽  
Triazole Derivatives

The enzyme tyrosine kinase BCR-Abl-1 is the main molecular target in the treatment of chronic myeloid leukemia and can be competitively inhibited by tyrosine kinase inhibitors such as imatinib. New potential competitive inhibitors were synthesized using the (phenylamino)pyrimidine-pyridine (PAPP) group as a pharmacophoric fragment, and these compounds were biologically evaluated. The synthesis of twelve new compounds was performed in three steps and assisted by microwave irradiation in a 1,3-dipolar cycloaddition to obtain 1,2,3-triazole derivatives substituted on carbon C-4 of the triazole nucleus. All compounds were evaluated for their inhibitory activities against a chronic myeloid leukemia cell line (K562) that expresses the enzyme tyrosine kinase BCR-Abl-1 and against healthy cells (WSS-1) to observe their selectivity. Three compounds showed promising results, with IC50 values between 1.0 and 7.3 μM, and were subjected to molecular docking studies. The results suggest that such compounds can interact at the same binding site as imatinib, probably sharing a competitive inhibition mechanism. One compound showed the greatest interaction affinity for BCR-Abl-1 in the docking studies.

Synthesis, Molecular Docking and In Vivo Biological Evaluation of Iminostilbene Linked 1,2,3-Triazole Pharmacophores as Promising AntiAnxiety and Anti-Inflammatory Agents

2021 ◽  
Vol 17 ◽  
Author(s):  
Kariyappa N. Ankali ◽  
Javarappa Rangaswamy ◽  
Mallappa Shalavadi ◽  
Nagaraja Naik
Keyword(s):  
Molecular Docking ◽  
Cycloaddition Reaction ◽  
Triazole Ring ◽  
Docking Studies ◽  
Biological Evaluation ◽  
Gaba A ◽  
Chemical Structures ◽  
Rat Paw Edema ◽  
Anti Inflammatory

Background: Iminostilbene and 1,2,3-triazole ring containing compounds are considered as beneficial substrates in drug design. Objectives: This study was aimed at the synthesis of novel series of iminostilbene linked 1,2,3- triazole pharmacophores (7c-n) by Cu(I) catalyzed 1,3 dipolar cycloaddition reaction between 5- (Prop-2-yn-1-yl)-5H-dibenzo[b,f]azepine (7b) and various substituted azidobenzene derivatives (3cn). Methods: The chemical structures of compounds were confirmed by 1 H NMR, 13C NMR, LC-MS and molecular docking studies were carried out through HEX docking software. Results: The in vivo anti anxiety capacity of the compounds was evaluated by using “elevated plus maze” (EPM), anxiety model. The results exhibited that compounds (7d, 7e, 7j and 7k) have a higher anti anxiety effect close to diazepam. The anti-inflammatory activities of the synthesized compounds were evaluated by “Carrageenan-induced rat paw edema” model, compounds (7b, 7c, 7d, 7f, and 7j) demonstrated statistically significant inflammatory activity. Molecular docking analysis revealed that compounds (7d, 7e and 7j) bound to GABA(A) proteins show more efficiency when compared to the other analogues in the series. Conclusion: These results suggest that compounds (7b, 7c, 7d, 7e, 7f, and 7j) can be considered as novel candidates for anti-anxiety and anti-inflammatory agents. Moreover, docking method was used to elucidate anti-anxiety effect of compounds. This study furnished insight into the molecular interactions of synthesized compounds with their physiological targets, and the potential to develop bioactive heterocyclic compounds.

Catecholated graphene-filled polyimide with enhanced mechanical, thermal, and tribological properties

2020 ◽  
pp. 095400832094035
Author(s):  
Xing Wu ◽  
Zhengyu Jin ◽  
Yuejin Zhu ◽  
Haichao Zhao
Keyword(s):  
Friction And Wear ◽  
In Situ Polymerization ◽  
Cycloaddition Reaction ◽  
Mechanical Analysis ◽  
Dipolar Cycloaddition ◽  
Wear Properties ◽  
Comprehensive Properties ◽  
Transmission Electron ◽  
Friction And Wear Tests

In order to achieve good dispersion of graphene in polyimide (PI), catecholated graphene (G-Cat) was prepared by 1,3-dipolar cycloaddition reaction of N-methylglycine and 3,4-dihydroxybenzaldehyde with graphene sheets. G-Cat/PI composites were prepared by in situ polymerization with pyromellitic dianhydride and 4,4-oxydianiline in the presence of G-Cat. The successful modification of graphene was proved by infrared spectroscopy, Raman spectroscopy, and transmission electron microscopy. The comprehensive properties of G-Cat/PI composites were studied by tensile, dynamic mechanical analysis, thermogravimetric analysis, and friction and wear tests. By observing the morphology of wear marks, the friction and wear properties of the composites were emphatically analyzed. Therefore, graphene/PI composites were expected to have broad application prospects in lubrication and wear resistance.

Uranyl triazolate formation via an in situ Huisgen 1,3-dipolar cycloaddition reaction

CrystEngComm ◽  
2011 ◽  
Vol 13 (1) ◽  
pp. 153-157 ◽  
Author(s):  
Karah E. Knope ◽  
Christopher L. Cahill
Keyword(s):  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition

Synthesis of New Hexakis-Heterocyclic Compounds and their Use in the Formation and Stabilization of Au and Ag Nanoparticles

2014 ◽  
Vol 976 ◽  
pp. 3-7
Author(s):  
María Isabel Montalvo-Sierra ◽  
Miriam A. Martins Alho ◽  
Ana María Herrera-Gonzalez ◽  
Jesús García-Serrano ◽  
Paola Belem Bocardo-Tovar
Keyword(s):  
Ir Spectroscopy ◽  
Ag Nanoparticles ◽  
Heterocyclic Compounds ◽  
Cyano Group ◽  
Cycloaddition Reaction ◽  
Aldehyde Group ◽  
Dipolar Cycloaddition ◽  
Vis Spectroscopy ◽  
Aldehyde Derivative

The stabilization of nanoparticles in solution is a challenge of major proportions, and avoiding the formation of aggregates and eventual coalescence of particles is directly linked to the conservation of its unique properties. In this work, we reported the synthesis of two hexakis-heterocyclic compounds, containing the tetrazole or 2-amino-1,3,4-thiadiazole group, respectively. The hexa-heterocyclic compounds were used in the synthesis and stabilization of Au and Ag nanoparticles. To obtain these molecules was used phosphonitrilic chloride trimer compound as core, which reacted with phenols properly substituted in theparaposition with either cyano or aldehyde group. The cyano group was successfully converted to the corresponding tetrazole using a 1,3-dipolar cycloaddition reaction with ammonium azide generatedin situ. In the case of aldehyde derivative, it was converted to the corresponding thiosemicarbazone, which was further cyclized using FeCl3. Compounds were characterized by RMN and IR spectroscopy. The UV-Vis spectroscopy was used for nanoparticles analysis.

Syntheses of Anomeric Pairs of New C-Nucleosides via 1,3-Dipolar Cycloaddition Reaction, Part II

1997 ◽  
Vol 52 (11) ◽  
pp. 1393-1400 ◽  
Author(s):  
Zahida Maqboor ◽  
Mashooda Hasan ◽  
Kevin T. Potts ◽  
Abdul Malik ◽  
Tanveer Ahmad Nizami ◽  
...  
Keyword(s):  
Comparative Study ◽  
Spectral Data ◽  
Cycloaddition Reaction ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Reasonable Degree ◽  
Subsequent Hydrolysis

Abstract 1,3-Dipolar cycloaddition of dipolarophiles (1) and (2) with endocyclic heterocyclic azomethine ylides (4), (14) and (24), prepared in situ, leads to the protected β-and α-C-nucleo-sides (7), (8), (17), (18), (27) and (28), respectively. These, on subsequent hydrolysis, provide the corresponding C-nucleosides. The structures of all the synthesized com pounds are con­ firmed through analytical and spectral data. The assignment of configuration at C -1′ position of the C-nucleosides could be done by a comparative study of the properties of the corre­sponding α and β anomers with a reasonable degree of certainity.

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