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Nicholas O. Schneider ; Kendra Gilreath ; Daniel J. Burkett , et al. Pharmaceuticals,2024,17(5):570. DOI: 10.3390/ph17050570
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Abstract: Glycogen synthase kinase-3 (GSK-3) is a serine/threonine kinase which plays a center role in the phosphorylation of a wide variety of proteins, generally leading to their inactivation. As such, GSK-3 is viewed as a therapeutic target. An ever-increasing number of small organic molecule inhibitors of GSK-3 have been reported. Phenylmethylene hydantoins are known to exhibit a wide range of inhibitory activities including for GSK-3β. A family of fourteen 2-heterocycle substituted methylene hydantoins (14, 17–29) were prepared and evaluated for the inhibition of GSK-3β at 25 μM. The IC50 values of five of these compounds was determined; the two best inhibitors are 5-[(4′-chloro-2-pyridinyl)methylene]hydantoin (IC50 = 2.14 ± 0.18 μM) and 5-[(6′-bromo-2-pyridinyl)methylene]hydantoin (IC50 = 3.39 ± 0.16 μM). The computational docking of the compounds with GSK-3β (pdb 1q41) revealed poses with hydrogen bonding to the backbone at Val135. The 5-[(heteroaryl)methylene]hydantoins did not strongly inhibit other metalloenzymes, demonstrating poor inhibitory activity against matrix metalloproteinase-12 at 25 μM and against human carbonic anhydrase at 200 μM, and were not inhibitors for Staphylococcus aureus pyruvate carboxylase at concentrations >1000 μM.
Keywords: nitrogen heterocycles ; glycogen synthase kinase 3β ; computational docking
Purchased from AmBeed: 63071-13-6 ; 53547-60-7 ; 31181-90-5 ; 34160-40-2 ; 4985-92-6 ; 1121-60-4 ; 54221-96-4 ; 55589-47-4 ; 500-22-1 ; 1805434-14-3
CAS No. : | 500-22-1 | MDL No. : | MFCD00006382 |
Formula : | C6H5NO | Boiling Point : | - |
Linear Structure Formula : | C5H4N(CHO) | InChI Key : | QJZUKDFHGGYHMC-UHFFFAOYSA-N |
M.W : | 107.11 | Pubchem ID : | 10371 |
Synonyms : |
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Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P210-P233-P240-P241-P242-P243-P261-P264-P270-P271-P272-P273-P280-P301+P312+P330-P303+P361+P353-P304+P340+P312-P305+P351+P338+P310-P333+P313-P370+P378-P403+P233-P403+P235-P405-P501 | UN#: | 1989 |
Hazard Statements: | H226-H302-H315-H317-H318-H335-H412 | Packing Group: | Ⅲ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | In methanol; at 75℃; for 12h;Autoclave; | A 25 ml Teflon-lined autoclave containing 6-amino-2-naphthnoic acid (370 mg, 2 mmol), 3-pyridinecarboxaldehyde (210 mg, 2 mmol), and methanol (20 ml) was sealed and heated at 75 °C for 12 h, and then air-cooled slowly for 24 h. The resulting yellow crystals were filtered, and washed with methanol (10 ml × 3) to give ligand (67percent yield). Anal. Calc. for C17H12N2O2: C, 73.90; H, 4.38; N, 10.14. Found: C 74.00; H 4.30; N 10.15percent. |