353287-68-0Relevant academic research and scientific papers
Transformation of 4-oxo-4H-[1]-benzopyran-3-carboxaldehydes into pyrazolo[3,4-b]pyridines
Stankovicova, Henrieta,Gaplovsky, Anton,Lacova, Margita,Chovancova, Jarmila,Puchala, Agnieszka
, p. 843 - 848 (2006)
Reaction of 6-methyl-4-oxo-4H-[1]-benzopyran-3-carboxaldehyde 1 with 5-amino-3-methyl-1-phenyl-pyrazole 2 in alcoholic reaction media in the presence of 4-toluenesulfonic acid as catalyst afforded 5-(2-hydroxy-5-methylbenzoyl)-3- methyl-1-phenyl-1H-pyrazo
Synthesis and evaluation of pyrazolo[3,4-b]pyridines and its structural analogues as TNF-α and IL-6 inhibitors
Bharate, Sandip B.,Mahajan, Tushar R.,Gole, Yogesh R.,Nambiar, Mahesh,Matan,Kulkarni-Almeida, Asha,Balachandran, Sarala,Junjappa,Balakrishnan, Arun,Vishwakarma, Ram A.
, p. 7167 - 7176 (2008/12/22)
In the present article, we have synthesized three different series of pyrazolo[3,4-b]pyridines and their structural analogues using novel synthetic strategy involving one-pot condensation of 5,6-dihydro-4H-pyran-3-carbaldehyde/2-formyl-3,4,6-tri-O-methyl-d-glucal /chromone-3-carbaldehyde with heteroaromatic amines. All synthesized compounds were evaluated for their anti-inflammatory activity against TNF-α and IL-6. Out of 28 compounds screened, 40, 51, 52 and 56 exhibited promising activity against IL-6 with 60-65% inhibition at 10 μM concentration. Amongst these, 51, 52 and 56 showed potent IL-6 inhibitory activity with IC50's of 0.2, 0.3 and 0.16 μM, respectively. Compound 56 was not cytotoxic in CCK-8 cells up to the concentration of >100 μM.
3-Formylchromones IV. The Rearrangement of 3-Formylchromone Enamines as a Simple, Facile Route to Novel Pyrazolo[3,4-b]pyridines and the Synthetic Utility of the Latter
Lacova, Margita,Puchala, Agnieszka,Soleanyova, Eva,Lac, Jan,Kois, Pavol,Chovancova, Jarmila,Rasala, Danuta
, p. 696 - 708 (2007/10/03)
One-pot and facile preparations of 6-(2-hydroxy-5-R-benzoyl)-4-methyl-2-R1-pyrazolo[3,4-b]pyridines 4a-o are described, using the reaction of 3-formyl chromones 1 with 5-amino-1-R1-pyrazoles 2. An enamine-intermediate 2-ethyloxy-6-R-3-(3-methyl-1-phenylpyrazol-5-ylaminomethylene)chroman-4-one 3 was isolated at lower temperatures. Acyloxy-derivatives 5 of compounds 4 were obtained by acylation with acid chlorides or acid anhydrides. Coumarins 6 substituted at the 3- and 4-positions were prepared from the pyrazolo[3,4-b]pyridines 4 by condensation reactions and hydrazones 7 were formed from their reaction with 2,4-dinitrophenyl hydrazine. Reactions under microwave irradiation proceeded significantly faster and with high yields.
