Literature

Abstract

Penta-N-methyl and hexa-N-methyl analogues of RA-VII, an antitumor bicyclic hexapeptide of plant origin, were prepared. In the former, the nitrogens of d-Ala-1 and Ala-4 and in the latter, those of d-Ala-1, Ala-2, and Ala-4 were methylated under the phase-transfer catalysis conditions. Their solution structures were established by NOESY experiments and the crystal structures by X-ray crystallography. Those two methylated analogues showed much weaker cytotoxicity against P-388 leukemia cells than the parent RA-VII.

DOI： 10.1016/j.bmc.2011.02.003

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

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

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

Bioorganic & Medicinal Chemistry Letters 2013.0

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