title: Synthesis, antioxidant and antimicrobial activity of novel vanillin derived piperidin-4-one oxime esters: preponderant role of the phenyl ester substituents on the piperidin-4-one oxime core.
abstract: The study has been achieved the efficient synthesis of vanillin derived piperidin-4-one oxime esters (5a-m) via four step reaction involved Mannich reaction of vanillin, acetone and ammonium acetate to obtain 2,6-bis(4-hydroxy-3-methoxyphenyl)-piperidin-4-one 2 followed by N-methylation and oximation. Further, to enhance the biological activity of vanillin derived piperidin-4-one oxime core, esterification of 4 with substituted benzoyl chlorides in the presence of strong organic base t-BuOK accomplished a series of vanillin derived piperidin-4-one oxime esters (5a-m). The synthesized analogues are screened for their antioxidant and antimicrobial studies and the preponderant effect of the phenyl ester substituents on the biological activity of piperidin-4-one oxime core was demonstrated. Among the tested compounds, 5i and 5j are emerged as outperformed antioxidants than standard Butylated hydroxy anisole (BHA) whereas, compounds 5b and 5d manifested potent antibacterial and antifungal activity than standard streptomycin and fluconazole respectively.
authors.affiliation: Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570006, Karnataka, India. st.harini988@gmail.com
authors.forename: Salakatte Thammaiah
authors.initials: ST
authors.lastname: Harini
authors.forename: Honnaiah Vijay
authors.initials: HV
authors.lastname: Kumar
authors.forename: Javarappa
authors.initials: J
authors.lastname: Rangaswamy
authors.forename: Nagaraja
authors.initials: N
authors.lastname: Naik
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001231:Aspergillus flavus / Q000187:drug effects; D001547:Benzaldehydes / Q000737:chemistry*; D002176:Candida albicans / Q000187:drug effects; D002912:Chrysosporium / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004926:Escherichia coli / Q000187:drug effects; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010091:Oximes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000975:Antioxidants; D001547:Benzaldehydes; D004952:Esters; D010091:Oximes; D010880:Piperidines; C100058:vanillin