Tetrahydronaphthalene compounds

Details Tetrahydronaphthalene compounds Tetrahydronaphthalene compounds

1996-02-27

1998-11-17

Achutamurthy, Ponnathapura

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Cyclic peptides

530326, 530327, 530328, 530329, 530330, 530333, 530335, 530338, 540455, 556420, 560 10, 560 19, 560 28, 562427, 562428, C07K 400, C07K 512, C07D28500

Patent

active

058378073

ABSTRACT:
This invention is directed to tetrahydronaphthalene compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, bromine, cyano, formyl, hydroxy, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, aryloxy, lower aralkoxy or aryl; R.sup.2 is an amino acid residue or a chain of 2 to 20 amino acid residues wherein reactive moieties in the side chains of the amino acid residue(s) is/are protected or unprotected, and wherein the amino group of the N-terminal amino acid is a free or protected amino group; A.sup.1, A.sup.2, A.sup.3 and A.sup.4 each are .alpha.-amino acid residues wherein A.sup.1 and A.sup.2 are in the L configuration and A.sup.3 and A.sup.4 are in the D configuration when the .alpha.-C atom of said .alpha.-amino acid residue is asymmetric; X is oxygen or sulphur; Y is a residue of the formula ##STR2## n is 0 or 1; R.sup.3 is hydrogen or lower alkyl; R.sup.4 is hydrogen or lower alkyl; and Z and the two C atoms together are an aromatic ring selected from the group of benzene, furan, thiophene, pyridine or pyrimidine, wherein said aromatic ring is substituted or unsubstituted; and salts thereof and their intermediates. The compounds are useful as mimetics of exposed helical domains of proteins in order to clarify their role with respect to interactions with other proteins or with DNA or RNA through .alpha.-helical conformation. They are therefore valuable aids in the determination of biologically active peptide sequences and are accordingly so-called "research tools". They are also potentially useful as medicaments.

REFERENCES:
Callahan, et al. The Use of .gamma.-Turn Mimetics to Define Peptide Secondary Structure, Tetrahedron vol. 49, No. 17 pp. 3479-3488 (1993).
Callahan, et al. Design and Synthesis of a C.sub.7 Mimetic for the Predicted .gamma.-Turn Conformation Found in Several Constrained RGD Antagonists.sup.1, J. Med. Chem, vol. 35, pp. 3970-3972 (1992).

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