title: An amidation/cyclization approach to the synthesis of N-hydroxyquinolinones and their biological evaluation as potential anti-plasmodial, anti-bacterial, and iron(II)-chelating agents.
abstract: A 26-member library of novel N-hydroxyquinolinone derivatives was synthesized by a one-pot Buchwald-type palladium catalyzed amidation and condensation sequence. The design of these rare scaffolds was inspired from N-hydroxypyridones and 2-quinolinones classes of compounds which have been shown to have rich biological activities. The synthesized compounds were evaluated for their anti-plasmodial and anti-bacterial properties. In addition, these compounds were screened for their iron(II)-chelation properties. Notably, four of these compounds exhibited anti-plasmodial activities comparable to that of the natural product cordypyridone B.
authors.affiliation: Department of Pharmacy, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore.
authors.forename: Yanbo
authors.initials: Y
authors.lastname: Teng
authors.affiliation: Singapore Immunology Network (SIgN), Agency for Science Technology and Research, (A(∗)STAR), 8A Biomedical Grove, Immunos Building, Singapore 138648, Singapore.
authors.forename: Rossarin
authors.initials: R
authors.lastname: Suwanarusk
authors.affiliation: Department of Pharmacy, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore.
authors.forename: Mun Hong
authors.initials: MH
authors.lastname: Ngai
authors.affiliation: Institute of Chemical and Engineering Sciences (ICES), Agency for Science Technology and Research, (A(∗)STAR), 8 Biomedical Grove, Singapore 138665, Singapore.
authors.forename: Rajavel
authors.initials: R
authors.lastname: Srinivasan
authors.affiliation: Singapore Immunology Network (SIgN), Agency for Science Technology and Research, (A(∗)STAR), 8A Biomedical Grove, Immunos Building, Singapore 138648, Singapore.
authors.forename: Alice Soh Meoy
authors.initials: AS
authors.lastname: Ong
authors.affiliation: Department of Microbiology, National University of Singapore, 5 Science Drive 2, Singapore 117545, Singapore.
authors.forename: Bow
authors.initials: B
authors.lastname: Ho
authors.affiliation: Singapore Immunology Network (SIgN), Agency for Science Technology and Research, (A(∗)STAR), 8A Biomedical Grove, Immunos Building, Singapore 138648, Singapore.
authors.forename: Laurent
authors.initials: L
authors.lastname: Rénia
authors.affiliation: Department of Pharmacy, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore; Institute of Chemical and Engineering Sciences (ICES), Agency for Science Technology and Research, (A(∗)STAR), 8 Biomedical Grove, Singapore 138665, Singapore.
authors.forename: Christina L L
authors.initials: CL
authors.lastname: Chai
mesh_terms: D000577:Amides / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D002614:Chelating Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003500:Cyclization; D004926:Escherichia coli / Q000187:drug effects; D005296:Ferrous Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D010961:Plasmodium / Q000187:drug effects; D015363:Quinolones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000577:Amides; D000900:Anti-Bacterial Agents; D000962:Antimalarials; D002614:Chelating Agents; D005296:Ferrous Compounds; D015363:Quinolones; D010165:Palladium
keywords: Anti-bacterial activity; Anti-plasmodial activity; Iron chelation; N-Hydroxyquinolinone