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Keywords = 3,5-pyridinedicarboxlic acid

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19 pages, 773 KiB  
Article
Synthesis and Biological Activities of Some New (Nα-Dinicotinoyl)- bis-L-Leucyl Linear and Macrocyclic Peptides
by Suzan Khayyat and Abd El-Galil Amr
Molecules 2014, 19(8), 10698-10716; https://doi.org/10.3390/molecules190810698 - 24 Jul 2014
Cited by 17 | Viewed by 5944
Abstract
A series of linear and macrocyclic peptides 312 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 [...] Read more.
A series of linear and macrocyclic peptides 312 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 79 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 10ae 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. Full article
(This article belongs to the Section Organic Chemistry)
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