Synthesis of novel isoxazole functionalized pyrazolo[3,4‐b]pyridine derivatives; their anticancer activity

Abstract

A series of novel isoxazole functionalized pyrazolo[3,4‐b]pyridine derivatives 5a‐n were prepared, respectively, initiated from 6‐thiophenyl‐4‐(trifluoromethyl)‐1H‐pyrazolo[3,4‐b]pyridin‐3‐amine 3 through selective N‐propargylation, and these N‐propargylated compounds 4 were cyclized with aryloximes by using of sodium hypochlorite, and obtained the title products 5a‐n. All the final products 5a‐n were submitted for anticancer activity against four cancer cell lines such as “HeLa—cervical cancer (CCL‐2); COLO 205—colon cancer (CCL‐222); HepG2—liver cancer (HB‐8065); MCF7—breast cancer (HTB‐22)”; Compounds 5c, 5d, and 5h are found to have more prominent anticancer activity at micro molar concentration.

Antibacterial evaluation and molecular properties of pyrazolo[3,4-b] pyridines and thieno[2,3-b]pyridines

“…In vitro antibacterial activities of pyrazolo [3,4-b] pyridines 6a-h and thieno[2,3-b]pyridines 8a-h were measured against B. subtilis and S. aureus as Gram-positive bacteria and also against Escherichia coli and Pseudomonas aeruginosa as NH 2 ), 7.29-7.89 (m, 14H, 2C 6 H 5 and C 6 H 4 ) Gram-negative bacteria species using a modified Kirby-Bauer disk diffusion method (Bauer et al, 1966;Osman et al, 2012).…”

“…Nitrogen heterocyclic compounds (triazine, benzimidazole, pyrazolopyrimidine, pyrazoloquinazoline, pyrazole, pyrazoline, and pyrazolo [3,4-d][1,2,3]triazine) are very important classes of compounds owing to their widespectrum of biological activities (Abd El-All et al, 2016;Adole et al, 2020;Chobe et al, 2014;El-Naggar et al, 2018;Hassan et al, 2016Hassan et al, , 2017Hassan et al, , 2018Jian et al, 2020;Magd-El-Din et al, 2018). In particular, pyrazolo [3,4-b]pyridines and thieno [2,3-b] pyridines (Elneairy et al, 2000;Mohi-El-Deen et al, 2019;Ravula et al, 2020;Saeedi et al, 2020) and 5-acetyl-4-amino-1-(1,2,4-triazin-3-yl)-pyrazolo [3,4-b]pyridine derivative I showed antibacterial activity with good inhibitions against Staphylococcus aureus and Staphylococcus epidermidis (Ali, 2009). 4- 3′:3,4]pyrazolo[5,1-c]-1,2,4-triazin-3,9dicarbonitrile II exhibited a remarkable cytotoxic activity against MCF-7 (ERα-dependent) cells (Nafie et al, 2020).…”

Synthesis, biological evaluation, and molecular docking studies of novel pyrazole, pyrazoline‐clubbed pyridine as potential antimicrobial agents

“…Pyridine is also an important heterocycle in medicinal chemistry and is associated with several pharmaceutical activities. [ 11–18 ] Figure 1 represents the concept of drug design based on commercially available drugs isoniazid, fezolamine, and dipyrone heterocycles.…”

Discovery of novel 3‐{[(5,5‐dimethyl‐4,5‐dihydroisoxazol‐3‐yl)sulfonyl]methyl}benzo[d]isoxazole analogs as promising very long chain fatty acids inhibitors

“…Benfuresate and ethofumesate are both benzofuran ring herbicides that can control annual or perennial grass weeds [40,41] . Benzoisoxazole, as an important biomedical molecular skeleton, has extremely high biological activity and pharmaceutical properties and is abundantly applied in drugs [42,43] . In agriculture, benzoisoxazole is mainly used in fungicides as a molecular active fragment, and less in herbicides [44] .…”

“…[40,41] Benzoisoxazole, as an important biomedical molecular skeleton, has extremely high biological activity and pharmaceutical properties and is abundantly applied in drugs. [42,43] In agriculture, benzoisoxazole is mainly used in fungicides as a molecular active fragment, and less in herbicides. [44] Therefore, benzoisoxazole might be a promising pharmacophore moiety to integrate with a five-membered ring pharmacophore of pyroxasulfone.…”