Synthesis of pyrazolo[3,4- b]pyridines under microwave irradiation in multi-component reactions and their antitumor and antimicrobial activities – Part 1

• Published in: European journal of medicinal chemistry Vol. 48; pp. 92 - 96
• Main Authors: El-borai, M.A., Rizk, H.F., Abd-Aal, M.F., El-Deeb, I.Y.
• Format: Journal Article
• Language: English
• Published: ISSY-LES-MOULINEAUX Elsevier Masson SAS 01.02.2012; Elsevier
• Subjects: Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - chemistry; Anti-Infective Agents - pharmacology; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antimicrobial activities; Antineoplastic agents; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Antitumor activities; Biological and medical sciences; Cell Line, Tumor; Cell Survival - drug effects; Chemistry, Medicinal; General aspects; Humans; Inhibitory Concentration 50; Life Sciences & Biomedicine; Liver Neoplasms - drug therapy; Magnetic Resonance Spectroscopy; Mass Spectrometry; Medical sciences; Microbial Sensitivity Tests; Microwave irradiation; Microwaves; Molecular Structure; Multi-component reactions; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Pyrazoles - chemical synthesis; Pyrazoles - chemistry; Pyrazoles - pharmacology; Pyrazolo[3,4- b]pyridine; Pyridines - chemical synthesis; Pyridines - chemistry; Pyridines - pharmacology; Science & Technology; Spectrophotometry, Infrared; Microwave irradiation; Multi-component reactions; Antimicrobial activities; Pyrazolo[3,4- b]pyridine; Antitumor activities; DERIVATIVES; SOLVENT; Pyrazolo[3,4-b]pyridine; Antineoplastic agent; Enterobacter cloacae; Nitrile; Escherichia coli; Liver; Bacillaceae; Antimicrobial agent; Pyridine derivatives; Fungi; Bacillales; Hepatocyte; Bacillus; Bacteria; Fungi Imperfecti; Chemical synthesis; Tumor cell; Enterobacteriaceae; Human; Fusarium oxysporum; Multicomponent reaction; Microwave heating; In vitro; Biological activity; Serratia; Operating conditions; Penicillium expansum; Cell line; Endophyte
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2011.11.038

An efficient one-pot synthesis in multi-component system (MRCs) for the preparation of pyrazolo[3,4- b]pyridine derivatives from the reaction of 5-amino-1-phenyl-3-(pyridin-3-yl)-1 H-pyrazole with 4-anisaldehyde and p-substituted β-ketonitriles or with pyruvic acid and some aromatic aldehydes in acetic acid medium. The reactions were carried out by two different techniques, conventional heating and microwave irradiation. These compounds were screened for their antibacterial activity against Gram-positive bacteria ( Bacillus), Gram-negative bacteria ( Escherichia coli, Enterobacter cloaca and serratia) and antifungal activity against Fusarium Oxysporum and Penicillium expansum. Also, among the synthesized compounds 4a– f tested for antitumor activity against liver cell line. Compounds 6-(4-Fluorophenyl)-4-(4-methoxyphenyl)-1-phenyl-3-(pyridin-3-yl)-1H-pyrazolo[3,4- b]pyridine-5-carbonitrile ( 4e) and 4-(4-Methoxyphenyl)-1-phenyl-3,6-di(pyridin-3-yl)-1H-pyrazolo[3,4- b] pyridine-5-carbonitrile ( 4a) showed the highest activity. Synthesis of some new pyrazolo[3,4- b]pyridine derivatives were reported. The reactions were carried out by conventional heating and microwave irradiation. Most of the synthesized compounds were screened for antimicrobial and antitumor activities. [Display omitted] ► Synthesis of 5-amino-1-phenyl-3-(pyridin-3-yl)-1 H-pyrazole was reported. ► Synthesis of pyrazolo[3,4- b]pyridine derivatives by one-pot cycleocondensation reaction. ► The reactions were carried out by conventional heating and microwave irradiation. ► Most of the synthesized compounds were screened for antimicrobial and antitumor activities.