Literature

Abstract

An aza-cycloisodityrosine analogue of RA-VII, 3, was designed and synthesized. The key aza-cycloisodityrosine unit was prepared by copper(II)-acetate-mediated intramolecular phenylamine/arylboronic acid coupling of dipeptide followed by connection with the tetrapeptide segment to afford a hexapeptide. Subsequent macrocyclization of the hexapeptide with EDC · HCl and HOOBt under dilute conditions gave 3. Analogue 3 showed significant cytotoxic activity against human promyelocytic leukemia HL-60 cells and human colon carcinoma HCT-116 cells, but its activity was weaker than that of parent peptide RA-VII (1).

DOI： 10.1016/j.bmcl.2013.10.033

Aza-cycloisodityrosine analogue of RA-VII, an antitumor bicyclic hexapeptide

Bioorganic & Medicinal Chemistry Letters 2013.0

Design and synthesis of a bis(cycloisodityrosine) analogue of RA-VII, an antitumor bicyclic hexapeptide

Bioorganic & Medicinal Chemistry Letters 2008.0

Synthesis of [Tyr-5-Ψ(CH2NMe)-Tyr-6]RA-VII, a reduced peptide bond analogue of RA-VII, an antitumor bicyclic hexapeptide

Bioorganic & Medicinal Chemistry Letters 2012.0

Per-N-methylated analogues of an antitumor bicyclic hexapeptide RA-VII

Bioorganic & Medicinal Chemistry 2011.0

Preparation and antitumor activity of [N-alkyl-Ala2]RA-VII, antitumor cyclic hexapeptide

Bioorganic & Medicinal Chemistry Letters 1994.0

Isolation, structural elucidation, and synthesis of RA-XVII, a novel bicyclic hexapeptide from Rubia cordifolia, and the effect of side chain at residue 1 upon the conformation and cytotoxic activity