Synthesis and Biological Activities of Some New (Nα-Dinicotinoyl)-bis-l-Leucyl Linear and Macrocyclic Peptides

Molecules

Suzan Khayyat¹ 

[1] Chemistry Department, Faculty of Science for Girls, King Abdulaziz University, Jeddah 31534, Kingdom of Saudi Arabia

关键词: 3;    5-pyridinedicarboxlic acid;    peptide coupling methods;    linear and macrocylic peptides;    biological activities;   

DOI  :  10.3390/molecules190810698

来源: mdpi

【 摘 要 】

A series of linear and macrocyclic peptides 3–12 were synthesized using 3,5-pyridinedicarboxylic acid (1) as starting material and screened for their antimicrobial, anti-inflammatory and anticancer activities. Bis-ester 3 was prepared from 1 and l-leucine methyl ester. Hydrazinolysis and hydrolysis of dipeptide methyl ester 3 with hydrazine hydrate or 1 N sodium hydroxide afforded compounds 4 and 5, respectively. Cyclization of the dipeptide 5 with l-lysine methyl ester afforded cyclic pentapeptide ester 6. Compounds 7–9 were synthesized by reacting hydrazide 4 with phthalic anhydride, 1,8-naphthalene anhydride or acetophenone derivatives. Treatment of acid hydrazide 4 with aromatic aldehydes or tetraacid dianhydrides afforded the corresponding bis-dipeptide hydrazones 10a–e and macrocyclic peptides 11 and 12, respectively. The structures of newly synthesized compounds were confirmed by IR, ¹H-NMR, MS spectral data and elemental analysis. The detailed synthesis, spectroscopic data, biological and pharmacological activities of the synthesized compounds was reported.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.