AN ACYLIMINIUM ION ROUTE TO CIS AND TRANS ANTI-PHE-GLY DIPEPTIDE MIMETICS

被引:37
作者
FLYNN, GA
BURKHOLDER, TP
HUBER, EW
BEY, P
机构
[1] Marion Merrell Dow Research Institute, Cincinnati, OH 45215
关键词
D O I
10.1016/S0960-894X(01)80814-3
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The synthesis of two series of constrained mimetics of the dipeptide phenylalanyl-glycine oriented in the "anti" conformation (X1 = 180-degrees) are described. These benzolactams differ about the geometry of the internal amide bond (omega-1 = 0-degrees or 180-degrees). Solution NMR studies support specific conformational assignments for these mimetics.
引用
收藏
页码:309 / 312
页数:4
相关论文
共 10 条
[1]  
BENISHAI D, 1977, TETRAHEDRON, V33, P881
[2]  
BENISHAI D, 1988, 20TH P EUR PEP S
[3]   THE CONVERSION OF A DIAZOLACTAM TO AN ALPHA-METHYLENELACTAM - AN ENTRANCE TO NEW CONFORMATIONALLY RESTRICTED INHIBITORS OF ANGIOTENSIN-CONVERTING ENZYME [J].
FLYNN, GA ;
BEIGHT, DW ;
HUBER, EW ;
BEY, P .
TETRAHEDRON LETTERS, 1990, 31 (06) :815-818
[4]   AN ACYL-IMINIUM ION CYCLIZATION ROUTE TO A NOVEL CONFORMATIONALLY RESTRICTED DIPEPTIDE MIMIC - APPLICATIONS TO ANGIOTENSIN-CONVERTING ENZYME-INHIBITION [J].
FLYNN, GA ;
GIROUX, EL ;
DAGE, RC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7914-7915
[5]  
Giroux E, 1989, J Enzyme Inhib, V2, P269, DOI 10.3109/14756368909088480
[6]  
MORELY JS, 1969, J CHEM SOC C, P809
[7]  
REHWINKEL H, 1982, SYNTHESIS-STUTTGART, P826
[8]  
SEEBACH D, 1982, SYNTHESIS-STUTTGART, P1138
[9]   2-TRIMETHYLSILYLETHYL RESIDUE, A SELECTIVELY CLEAVABLE CARBOXYL PROTECTING GROUP [J].
SIEBER, P .
HELVETICA CHIMICA ACTA, 1977, 60 (08) :2711-2716
[10]   MIXED ANHYDRIDES IN PEPTIDE-SYNTHESIS - INFLUENCE OF THE SOLVENT AND THE AMINE ON THE RACEMIZATION OF DMET RESIDUE OF AN ENKEPHALIN SEQUENCE [J].
TORRES, JL ;
HARO, I ;
VALENCIA, G ;
ANTON, JMG ;
REIG, F .
TETRAHEDRON, 1987, 43 (17) :4031-4034