A convenient method for the synthesis of N-hydroxyureas

被引:21
作者
Parrish, DA [1 ]
Zou, Z [1 ]
Allen, CL [1 ]
Day, CS [1 ]
King, SB [1 ]
机构
[1] Wake Forest Univ, Dept Chem, Winston Salem, NC 27109 USA
基金
美国国家卫生研究院; 美国国家科学基金会;
关键词
N-hydroxyureas; nitric oxide; nitric oxide donors; carbohydrates; hydrogenation;
D O I
10.1016/j.tetlet.2005.10.091
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of amines with 1-(4-nitrophenol)-N-(O-benzylhydroxy)carbamate yields the O-benzyl protected N-hydroxyureas. Hydrogenation of the O-benzyl protected N-hydroxyureas over 5% Pd/BaSO4 cleanly gives the N-hydroxyureas ill good yield. In addition to primary and secondary aliphatic and aromatic amines, this method converts amino sugars to the corresponding N-hydroxyureas without extensive protecting group chemistry. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8841 / 8843
页数:3
相关论文
共 14 条
[1]   Modulators of leukotriene biosynthesis and receptor activation [J].
Brooks, CDW ;
Summers, JB .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (14) :2629-2654
[2]   N-(Hydroxyaminocarbonyl)phenylalanine:: A novel class of inhibitor for carboxypeptidase A [J].
Chung, SJ ;
Kim, DH .
BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (01) :185-189
[3]  
CRAMER FD, 1963, METHODS CARBOHYDR CH, V2, P244
[4]  
Donehower RC, 1996, CANC CHEMOTHERAPY BI, P253
[5]   The role of hydroxyurea in sickle cell disease [J].
Halsey, C ;
Roberts, IAG .
BRITISH JOURNAL OF HAEMATOLOGY, 2003, 120 (02) :177-186
[6]   Zinc(II)-mediated inhibition of a ribonuclease by an N-hydroxyurea nudeotide [J].
Higgin, JJ ;
Yakovlev, GI ;
Mitkevich, VA ;
Makarov, AA ;
Raines, RT .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (03) :409-412
[7]   The synthesis and cytotoxicity of fructose-1-SNAP, a novel fructose conjugated S-nitroso nitric oxide donor [J].
Hou, YC ;
Wu, XJ ;
Xie, WH ;
Braunschweiger, PG ;
Wang, PG .
TETRAHEDRON LETTERS, 2001, 42 (05) :825-829
[8]   Synthesis and evaluation of new sulfur-containing L-arginine-derived inhibitors of nitric oxide synthase [J].
Ichimori, K ;
Stuehr, DJ ;
Atkinson, RN ;
King, SB .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (10) :1842-1848
[9]   The nitric oxide producing reactions of hydroxyurea [J].
King, SB .
CURRENT MEDICINAL CHEMISTRY, 2003, 10 (06) :437-452
[10]   QUENCHING OF TYROSINE RADICALS OF M2 SUBUNIT FROM RIBONUCLEOTIDE REDUCTASE IN TUMOR-CELLS BY DIFFERENT ANTITUMOR AGENTS - AN EPR STUDY [J].
LIERMANN, B ;
LASSMANN, G ;
LANGEN, P .
FREE RADICAL BIOLOGY AND MEDICINE, 1990, 9 (01) :1-4