Abstract
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.
Highlights
Macrocyclic azacrowns and their complexing derivatives are interesting compounds in the macrocyclic chemistry area [1,2,3]
In view of these observations and as continuation of our previous work [6,7,8,9,10,11,12,13,14,15,16,17,18,19] in macrocyclic and heterocyclic chemistry, we have synthesized some new linear and macrocyclic peptides containing amino acid and pyridine moieties and some of the synthesized compounds were screened for their antimicrobial, anti-inflammatory and anticancer activities compared to the reference drugs
The synthesis of Nα-dinicotinoyl-bis-(amino acid) methyl ester 3 was based on 3,5-pyridinedicarbonyl dichloride (2) which was obtained by conversion of compound 1 via reaction with thionyl chloride [25]
Summary
Macrocyclic azacrowns and their complexing derivatives are interesting compounds in the macrocyclic chemistry area [1,2,3]. Synthesis of some new potential bis-intercallators based on chiral pyridine-2,6dicarboxamides was reported [24] In view of these observations and as continuation of our previous work [6,7,8,9,10,11,12,13,14,15,16,17,18,19] in macrocyclic and heterocyclic chemistry, we have synthesized some new linear and macrocyclic peptides containing amino acid and pyridine moieties and some of the synthesized compounds were screened for their antimicrobial, anti-inflammatory and anticancer activities compared to the reference drugs
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