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Synthesis and Biological Activities of Some New (N(α)-Dinicotinoyl)-bis-l-Leucyl Linear and Macrocyclic Peptides
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...
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271395/ https://www.ncbi.nlm.nih.gov/pubmed/25061721 http://dx.doi.org/10.3390/molecules190810698 |
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author | Khayyat, Suzan Amr, Abd El-Galil |
author_facet | Khayyat, Suzan Amr, Abd El-Galil |
author_sort | Khayyat, Suzan |
collection | PubMed |
description | 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, (1)H-NMR, MS spectral data and elemental analysis. The detailed synthesis, spectroscopic data, biological and pharmacological activities of the synthesized compounds was reported. |
format | Online Article Text |
id | pubmed-6271395 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62713952018-12-27 Synthesis and Biological Activities of Some New (N(α)-Dinicotinoyl)-bis-l-Leucyl Linear and Macrocyclic Peptides Khayyat, Suzan Amr, Abd El-Galil Molecules Article 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, (1)H-NMR, MS spectral data and elemental analysis. The detailed synthesis, spectroscopic data, biological and pharmacological activities of the synthesized compounds was reported. MDPI 2014-07-24 /pmc/articles/PMC6271395/ /pubmed/25061721 http://dx.doi.org/10.3390/molecules190810698 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). |
spellingShingle | Article Khayyat, Suzan Amr, Abd El-Galil Synthesis and Biological Activities of Some New (N(α)-Dinicotinoyl)-bis-l-Leucyl Linear and Macrocyclic Peptides |
title | Synthesis and Biological Activities of Some New (N(α)-Dinicotinoyl)-bis-l-Leucyl Linear and Macrocyclic Peptides |
title_full | Synthesis and Biological Activities of Some New (N(α)-Dinicotinoyl)-bis-l-Leucyl Linear and Macrocyclic Peptides |
title_fullStr | Synthesis and Biological Activities of Some New (N(α)-Dinicotinoyl)-bis-l-Leucyl Linear and Macrocyclic Peptides |
title_full_unstemmed | Synthesis and Biological Activities of Some New (N(α)-Dinicotinoyl)-bis-l-Leucyl Linear and Macrocyclic Peptides |
title_short | Synthesis and Biological Activities of Some New (N(α)-Dinicotinoyl)-bis-l-Leucyl Linear and Macrocyclic Peptides |
title_sort | synthesis and biological activities of some new (n(α)-dinicotinoyl)-bis-l-leucyl linear and macrocyclic peptides |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271395/ https://www.ncbi.nlm.nih.gov/pubmed/25061721 http://dx.doi.org/10.3390/molecules190810698 |
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