CS-1 peptidomimetics, compositions and methods of using the same

A peptide of the following formula:

• X--Y-Asp-(Xaa).sub.t Z
• wherein
• X is selected from the group consisting of phenylacetyl, pyridine-4-carbonyl, pyridine-3-acetyl, anilinocarbonyl, pyridine-3-carbonyl, biotinoyl-.epsilon.-amidocaproyl phenylalanyl, phthalimido, Europium-labeled .epsilon.-amidocaproyl phenylalanyl, 3,4-dihydroxyphenylacetyl, benzoyl, 3-quinolinecarbonyl, 1,2,3,4-tetrahydroquinazoline-2,4-dione-3-yl, prolinyl, GlcNAC-O(CH.sub.2).sub.5 -CO-phenylalanyl, acetyl phenylalanyl, benzyloxycarbonyl, (5-phenyl)hydantoinyl, pyrazolecarbonyl, 4-pyridinecarbonyl, pivaloyl, phenylpropionyl and phenylalanyl;
• Y is selected from the group consisting of leucyl and cyclohexylalanyl;
• Asp is an aspartyl residue;
• Xaa is an amino acid residue selected from the group consisting of phenylalaninyl, tyrosinyl, leucyl, tryptophanyl, valinyl, homophenylalanyl, phenylglycinyl, and p-nitrophenylalanyl;
• t is 0 or 1;
• when t is 1, substituent Z, together with the carbonyl group of Xaa, is selected from the group consisting of morpholinamide, D-proline amide, 4-hydroxypiperidinamide, piperazinamide, proline amide, pyrrolidinamide, 3,4-dihydroxypyrrolidinamide, 2-(hydroxymethyl)- prolinamide, piperidinamide and an amide formed between a C-terminal proline carboxyl and a tetraethylenepentamine moiety to which is bonded four peptides, each of which has the formula N-phenylacetyl-leucyl-aspartyl-phenylalanyl-proline;
• and
• when t is 0, substituent Z, together with the .alpha.-carbonyl group of Asp, is selected from the group consisting of N-›1-(carboxamidomethyl)-caprolactam-3-yl!amide, N-((1-carboxamidomethyl)2-oxo-tetrahydroquinolin-3-yl)amide, N-(amino-6,7-fused ring lactam)amide, N-(2-oxo-tetrahydroquinolin-3-yl)amide, N-(2-oxo-tetrahydroquinolin-3-yl)amide, N-(caprolactam-3-yl)-amide, N-(1-(2-N-morpholinylethyl)-2-oxotetrahydroquinoline-3-yl)amide, benzylamide, phenylethylamide, N-D-(caprolactam-3-yl)amide, and N-(2-N-morpholinyl)ethylamide.