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Molecules 2014, 19(8), 10698-10716; doi:10.3390/molecules190810698

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

1
Chemistry Department, Faculty of Science for Girls, King Abdulaziz University, Jeddah 31534, Kingdom of Saudi Arabia
2
Pharmaceutical Chemistry Department, College of Pharmacy, King Saud University, Riyadh 11451, Kingdom of Saudi Arabia
3
Applied Organic Chemistry Department, National Research Center, Dokki 12622, Cairo, Egypt
*
Author to whom correspondence should be addressed.
Received: 4 June 2014 / Revised: 4 July 2014 / Accepted: 11 July 2014 / Published: 24 July 2014
(This article belongs to the Section Organic Synthesis)
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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 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. View Full-Text
Keywords: 3,5-pyridinedicarboxlic acid; peptide coupling methods; linear and macrocylic peptides; biological activities 3,5-pyridinedicarboxlic acid; peptide coupling methods; linear and macrocylic peptides; biological activities
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MDPI and ACS Style

Khayyat, S.; Amr, A.E.-G. Synthesis and Biological Activities of Some New (Nα-Dinicotinoyl)- bis-L-Leucyl Linear and Macrocyclic Peptides. Molecules 2014, 19, 10698-10716.

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