Solid-phase synthesis of biologically interesting compounds containing hydroxamic acid moiety

被引:12
作者
Krchnák, V [1 ]
机构
[1] Univ Notre Dame, Dept Chem & Biochem, Nieuwland Sci Ctr 251, Notre Dame, IN 46556 USA
关键词
hydroxamic acid; hydroxamate; solid-phase synthesis;
D O I
10.2174/138955706775197811
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Chemical strategies developed for the solid-phase synthesis of hydroxamates are divided into four groups: (i) the traditional synthesis of hydroxamates via cleavage of resin-bound esters by hydroxylamine and its derivatives, (ii) introduction of hydroxamic acid moiety on the resin-bound precursor, (iii) transformation of polymer-supported hydroxylamine, attached to a solid supported linker either by oxygen (O-linking strategy) or by nitrogen (N-linking strategy), and (iv) synthesis of N-alkyl hydroxamates. The scope and limitation of individual approaches are discussed.
引用
收藏
页码:27 / 36
页数:10
相关论文
共 55 条
[1]   Solid-phase synthesis of hydroxamic acid based TNF-α convertase inhibitors [J].
Barlaam, B ;
Koza, P ;
Berriot, J .
TETRAHEDRON, 1999, 55 (23) :7221-7232
[2]   A novel linkage for the solid-phase synthesis of hydroxamic acids [J].
Bauer, U ;
Ho, WB ;
Koskinen, AMP .
TETRAHEDRON LETTERS, 1997, 38 (41) :7233-7236
[3]  
Bui CT, 2000, BIOTECHNOL BIOENG, V71, P91
[4]   3-thiopropionic acid as a highly versatile multidetachable thioester resin linker [J].
Camarero, JA ;
Adeva, A ;
Muir, TW .
LETTERS IN PEPTIDE SCIENCE, 2000, 7 (01) :17-21
[5]   ADVANTAGEOUS APPLICATIONS OF AZABENZOTRIAZOLE (TRIAZOLOPYRIDINE)-BASED COUPLING REAGENTS TO SOLID-PHASE PEPTIDE-SYNTHESIS [J].
CARPINO, LA ;
EL-FAHAM, A ;
MINOR, CA ;
ALBERICIO, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (02) :201-203
[6]   Solid phase synthesis of peptide hydroxamic acids [J].
Chen, JJ ;
Spatola, AF .
TETRAHEDRON LETTERS, 1997, 38 (09) :1511-1514
[7]   Synthesis and functional characterization of novel derivatives related to oxotremorine and oxotremorine-M [J].
Dallanoce, C ;
Conti, P ;
De Amici, M ;
De Micheli, C ;
Barocelli, E ;
Chiavarini, M ;
Ballabeni, V ;
Bertoni, S ;
Impicciatore, M .
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (08) :1539-1547
[8]  
Dankwardt SM, 1998, SYNLETT, P761
[9]   Amino acid derived sulfonamide hydroxamates as inhibitors of procollagen C-proteinase. Part 2: Solid-phase optimization of side chains [J].
Dankwardt, SM ;
Abbot, SC ;
Broka, CA ;
Martin, RL ;
Chan, CS ;
Springman, EB ;
Van Wart, HE ;
Walker, KAM .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (08) :1233-1235
[10]   Amino acid derived sulfonamide hydroxamates as inhibitors of procollagen C-proteinase: Solid-phase synthesis of ornithine analogues [J].
Dankwardt, SM ;
Martin, RL ;
Chan, CS ;
Van Wart, HE ;
Walker, KAM ;
Delaet, NG ;
Robinson, LA .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (16) :2085-2088