Abstract
The present work describes the synthesis of a novel series of heterocyclic moieties derived from 5-acetylpyrazolo[3,4-b]pyridine (1). The formation of chalcones (2a-d) was utilized to synthesize pyrazoline, isoxazoline and pyrimidine derivatives (3-10). Thiosemicarbazone and semicarbazone (11, 17) were utilized to synthesize other new triazolethiones, thiadiazole and selenadiazole derivatives (11-19). Some new spiro derivatives (22-25) were synthesized by the reaction of chalcone (21) of 1 and isatine with hydrazines, hydroxyl amines and thiourea. Also, The reaction of 1 with cyanoacetyl hydrazine gave the hydrazide-hydrazone derivative 26, which was allowed to react with aromatic aldehydes and α-cyanocinnamonitrile to afford coumarine and substituted pyridine derivatives (28, 29). The structures of all the new compounds have been established on the basis of their analytical and spectral data. Twenty two of the synthesized compounds were also evaluated for their antibacterial and antifungal activity against various strains of bacteria and fungi and most are found to possess promising antimicrobial activity when compared with Chloramphenicol and Clotrimazole
Highlights
The pyrazolo[3,4-b]pyridine moieties represent important building blocks in both natural and synthetic bioactive compounds. 1 They are attractive targets in organic synthesis due to their significant biological activities such as xanthine oxidase inhibitors, cholesterol formation-inhibitor, and Anti-Alzheimer, 2,3 analgesic, 4 anxiolytic, 5 hypnotic, 6 antiviral, 7 anti-HIV, 8 corticotropin-Releasing Factor (CRF) antagonist, 9,10 antidiabetic, antiarrhythmic, antitumor, antimalarial
14 They show antimicrobial and antiparasitic activities. 15-17 In addition, they are used as anti-HIV-1,18 as a potential glucocorticoid receptor ligand for positron emission tomography (PET). It was found that some derivatives of pyrazolo[3,4-b]pyridine were belived to be effective as antileishmanial agents, inhibitors of erectile dysfunctions
21 Taking all the above into consideration and in continuation of our previous work directed to synthesis of new heterocycles engaged with pyrazole nuclei, 22-25 we describe the utilization of the 1-(3,6-dimethyl-1-phenyl-1H-pyrazolo[3,4b]pyridine-5-yl)ethanone (1) as the key intermediate in the synthesis of novel pyrazolo[3,4-b]pyridine members along with studies of the effect of some of them as antifungal and as antibacterial agents
Summary
The pyrazolo[3,4-b]pyridine moieties represent important building blocks in both natural and synthetic bioactive compounds. 1 They are attractive targets in organic synthesis due to their significant biological activities such as xanthine oxidase inhibitors, cholesterol formation-inhibitor, and Anti-Alzheimer, 2,3 analgesic, 4 anxiolytic, 5 hypnotic, 6 antiviral, 7 anti-HIV, 8 corticotropin-Releasing Factor (CRF) antagonist, 9,10 antidiabetic, antiarrhythmic, antitumor, antimalarial. 1 They are attractive targets in organic synthesis due to their significant biological activities such as xanthine oxidase inhibitors, cholesterol formation-inhibitor, and Anti-Alzheimer, 2,3 analgesic, 4 anxiolytic, 5 hypnotic, 6 antiviral, 7 anti-HIV, 8 corticotropin-Releasing Factor (CRF) antagonist, 9,10 antidiabetic, antiarrhythmic, antitumor, antimalarial. It was found that some derivatives of pyrazolo[3,4-b]pyridine were belived to be effective as antileishmanial agents, inhibitors of erectile dysfunctions. Taking all the above into consideration and in continuation of our previous work directed to synthesis of new heterocycles engaged with pyrazole nuclei, 22-25 we describe the utilization of the 1-(3,6-dimethyl-1-phenyl-1H-pyrazolo[3,4b]pyridine-5-yl)ethanone (1) as the key intermediate in the synthesis of novel pyrazolo[3,4-b]pyridine members along with studies of the effect of some of them as antifungal and as antibacterial agents
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
