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Synthesis, in vitro β-glucuronidase inhibitory activity and in silico studies of novel (E)-4-Aryl-2-(2-(pyren-1-ylmethylene)hydrazinyl)thiazoles
- Source :
- Bioorganic chemistry. 70
- Publication Year :
- 2016
-
Abstract
- Current research is based on the synthesis of novel ( E )-4-aryl-2-(2-(pyren-1-ylmethylene)hydrazinyl)thiazole derivatives ( 3 – 15 ) by adopting two steps route. First step was the condensation between the pyrene-1-carbaldehyde ( 1 ) with the thiosemicarbazide to afford pyrene-1-thiosemicarbazone intermediate ( 2 ). While in second step, cyclization between the intermediate ( 2 ) and phenacyl bromide derivatives or 2-bromo ethyl acetate was carried out. Synthetic derivatives were structurally characterized by spectroscopic techniques such as EI-MS, 1 H NMR and 13 C NMR. Stereochemistry of the iminic double bond was confirmed by NOESY analysis. All pure compounds 2 – 15 were subjected for in vitro β -glucuronidase inhibitory activity. All molecules were exhibited excellent inhibition in the range of IC 50 = 3.10 ± 0.10–40.10 ± 0.90 μM and found to be even more potent than the standard d -saccharic acid 1,4-lactone (IC 50 = 48.38 ± 1.05 μM). Molecular docking studies were carried out to verify the structure-activity relationship. A good correlation was perceived between the docking study and biological evaluation of active compounds.
- Subjects :
- Double bond
Stereochemistry
010402 general chemistry
01 natural sciences
Biochemistry
Saccharic acid
chemistry.chemical_compound
Structure-Activity Relationship
Drug Discovery
Structure–activity relationship
Animals
Enzyme Inhibitors
Thiazole
Molecular Biology
Glucuronidase
chemistry.chemical_classification
010405 organic chemistry
Organic Chemistry
Phenacyl bromide
0104 chemical sciences
Molecular Docking Simulation
Thiazoles
chemistry
Docking (molecular)
Proton NMR
Cattle
Two-dimensional nuclear magnetic resonance spectroscopy
Subjects
Details
- ISSN :
- 10902120
- Volume :
- 70
- Database :
- OpenAIRE
- Journal :
- Bioorganic chemistry
- Accession number :
- edsair.doi.dedup.....e9b8b520d65c69670a4a90bd167acb15