title: Metal-Free Direct Amidation of Naphthoquinones Using Hydroxamic Acids as an Amide Source: Application in the Synthesis of an HDAC6 Inhibitor.
abstract: A novel synthetic approach to amidoquinones by the reaction of naphthoquinones with hydroxamic acids under basic conditions was developed. The reaction is mild and operationally simple, and it affords high yields of amidoquinones. With this new method, a novel, very strong HDAC6 inhibitor, which showed high toxicity to AML cells, was successfully synthesized.
authors.affiliation: Department of Applied Chemistry, China Agricultural University , 2 Yuanmingyuan West Road, Beijing 100193, China.
authors.forename: Cheng
authors.initials: C
authors.lastname: Zhang
authors.affiliation: Department of Drug Discovery and Biomedical Sciences, Medical University of South Carolina , 280 Calhoun Street, MSC140 QF307, Charleston, South Carolina 29425, United States.
authors.forename: C James
authors.initials: CJ
authors.lastname: Chou
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D000073864:Histone Deacetylase 6 / Q000037:antagonists & inhibitors* / Q000378:metabolism; D056572:Histone Deacetylase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D006877:Hydroxamic Acids / Q000737:chemistry*; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry*; D011994:Recombinant Proteins / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D000577:Amides; D056572:Histone Deacetylase Inhibitors; D006877:Hydroxamic Acids; D009285:Naphthoquinones; D011994:Recombinant Proteins; C433811:HDAC6 protein, human; D000073864:Histone Deacetylase 6