[MerDABCO-SO3H]Cl catalyzed synthesis, antimicrobial and antioxidant evaluation and molecular docking study of pyrazolopyranopyrimidines

• Published in: Journal of molecular structure Vol. 1242; p. 130672
• Main Authors: Patil, Pradeep, Yadav, Archana, Bavkar, Laxman, N, Nippu B, Satyanarayan, N D, Mane, Ananda, Gurav, Akshay, Hangirgekar, Shankar, Sankpal, Sandeep
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15-10-2021
• Subjects: Antimicrobial activity; Antioxidant activity; Docking; Ionic liquid; Polymer support; Pyrazolopyranopyrimidines; Polymer support; Docking; Antimicrobial activity; Pyrazolopyranopyrimidines; Antioxidant activity; Ionic liquid
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2021.130672

•Introduction of novel polymer supported [MerDABCO-SO3H]Cl catalyst for the synthesis of pyrazolopyranopyrimidines.•High TON-TOF values.•Reusability of the catalyst for four runs.•Use of water as green solvent.•Promising antioxidant and antimicrobial activities of pyrazolopyranopyrimidines.•Greater interaction and affinity of pyrazolopyranopyrimidines with protein observed in docking study.
Sulfonic acid functionalized 1,4-diazabicyclo[2.2.2]octane supported on Merrifield resin, [MerDABCO-SO3H]Cl catalyst was prepared and explored in one-pot four-component reaction of ethyl acetoacetate, hydrazine hydrate, aryl aldehyde and barbituric acid for the synthesis of pyrazolopyranopyrimidines with excellent yields. The catalyst could be easily recovered and reused for four cycles without significant decrease in catalytic activity. The antimicrobial and invitro antioxidant activities of the synthesized pyrazolopyranopyrimidines were found to be promising and antioxidant activities are supported by molecular docking studies.
Sulfonic acid functionalized 1,4-diazabicyclo[2.2.2]octane supported on Merrifield resin, [MerDABCO-SO3H]Cl catalyst was prepared and explored in one pot condensation reaction of ethyl acetoacetate, hydrazine hydrate, aryl aldehydes and barbituric acid in aqueous medium for the synthesis of pyrazolopyranopyrimidines. The catalyst could be easily recovered and reused for four cycles without significant decrease in catalytic activity and product yields. The antimicrobial and in-vitro antioxidant activities of the synthesized pyrazolopyranopyrimidines were found to be promising and are supported by molecular docking studies. [Display omitted]