Synthesis of some novel dipeptides and their copper(II) complexes of (dibenzo [b, d] furan-2-ylsulfonyl) phenylalanine

Abstract

A new series of dipeptide candidates (6-11) and corresponding octahedral copper complexes (12-15) were prepared by the synthesis of dibenzofuran-2-sulfonyl chloride (3). Then, the acid chloride (3) was coupled, at low temperature, with DL-phenylalanine using triethylamine and gave the corresponding acid (4) as starting material, which was converted to dibenzofuran-2-sulphonyl-DL-phenylalanyl chloride (5) using thionyl chloride. The latter acid chloride (5) was coupled with some aliphatic amino acids and gave the corresponding dibenzofuran-2-sulphonyldipeptide candidates (6, 7). Moreover, dibenzofuran-2-sulphonyldipeptide methyl ester derivatives (8, 9) were prepared via the esterification of the corresponding candidates (6, 7) and hydrazinolysis with hydrazine hydrate 99% of methyl esters (8, 9) to give the corresponding peptide hydrazides (10, 11). Then, all the newly prepared peptide derivatives (6-11) were reacted with copper acetate to afford the corresponding copper complexes (12-15). The newly synthesized compounds (6-15) were characterized.

KEY WORDS: Dibenzofuran-2-sulfonyl-DL-phenylalanyl chloride, Amino acids, Linear dipeptides, Copper complexes.

Bull. Chem. Soc. Ethiop. 2025, 39(2), 301-311.                                                              

DOI: https://dx.doi.org/10.4314/bcse.v39i2.9