title: Fast and Facile Synthesis of 4-Nitrophenyl 2-Azidoethylcarbamate Derivatives from N-Fmoc-Protected α-Amino Acids as Activated Building Blocks for Urea Moiety-Containing Compound Library.
abstract: A fast and facile synthesis of a series of 4-nitrophenyl 2-azidoethylcarbamate derivatives as activated urea building blocks was developed. The N-Fmoc-protected 2-aminoethyl mesylates derived from various commercially available N-Fmoc-protected α-amino acids, including those having functionalized side chains with acid-labile protective groups, were directly transformed into 4-nitrophenyl 2-azidoethylcarbamate derivatives in 1 h via a one-pot two-step reaction. These urea building blocks were utilized for the preparation of a series of urea moiety-containing mitoxantrone-amino acid conjugates in 75-92% yields and parallel solution-phase synthesis of a urea compound library consisted of 30 members in 38-70% total yields.
authors.affiliation: School of Pharmacy, College of Medicine, ‡Molecular Probes Development Core, Molecular Imaging Center, and §Center for Innovative Therapeutics Discovery, National Taiwan University , 17, Xuzhou Road, Room 936, Taipei 10055, Taiwan.
authors.forename: Ying-Ying
authors.initials: YY
authors.lastname: Chen
authors.affiliation: School of Pharmacy, College of Medicine, ‡Molecular Probes Development Core, Molecular Imaging Center, and §Center for Innovative Therapeutics Discovery, National Taiwan University , 17, Xuzhou Road, Room 936, Taipei 10055, Taiwan.
authors.forename: Li-Te
authors.initials: LT
authors.lastname: Chang
authors.affiliation: School of Pharmacy, College of Medicine, ‡Molecular Probes Development Core, Molecular Imaging Center, and §Center for Innovative Therapeutics Discovery, National Taiwan University , 17, Xuzhou Road, Room 936, Taipei 10055, Taiwan.
authors.forename: Hung-Wei
authors.initials: HW
authors.lastname: Chen
authors.affiliation: School of Pharmacy, College of Medicine, ‡Molecular Probes Development Core, Molecular Imaging Center, and §Center for Innovative Therapeutics Discovery, National Taiwan University , 17, Xuzhou Road, Room 936, Taipei 10055, Taiwan.
authors.forename: Chia-Ying
authors.initials: CY
authors.lastname: Yang
authors.affiliation: School of Pharmacy, College of Medicine, ‡Molecular Probes Development Core, Molecular Imaging Center, and §Center for Innovative Therapeutics Discovery, National Taiwan University , 17, Xuzhou Road, Room 936, Taipei 10055, Taiwan.
authors.forename: Ling-Wei
authors.identifier: 0000-0001-5018-4491
authors.initials: LW
authors.lastname: Hsin
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000191:economics / Q000379:methods; D005449:Fluorenes / Q000138:chemical synthesis / Q000737:chemistry*; D008872:Microwaves; D009596:Nitrophenols / Q000138:chemical synthesis / Q000737:chemistry*; D054852:Small Molecule Libraries / Q000138:chemical synthesis / Q000737:chemistry*; D014508:Urea / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D014520:Urethane / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: D000596:Amino Acids; D001386:Azides; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D009596:Nitrophenols; D054852:Small Molecule Libraries; C024719:4-nitrophenyl; D014520:Urethane; D014508:Urea
keywords: amino acid; microwave-assisted; one-pot synthesis; parallel synthesis; urea building block