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Molecules 2012, 17(12), 14510-14521; doi:10.3390/molecules171214510
Article

Synthesis of New Macrocyclic Polyamides as Antimicrobial Agent Candidates

1, 2,3, 4, 4 and 1,2,*
1 Applied Organic Chemistry Department, National Research Center, Dokki 12622, Cairo, Egypt 2 Pharmaceutical Chemistry Department, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia 3 Pharmaceutical Chemistry Department, Drug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia 4 Photochemistry Department, National Research Center, Dokki 12622, Cairo, Egypt
* Author to whom correspondence should be addressed.
Received: 17 September 2012 / Revised: 26 November 2012 / Accepted: 28 November 2012 / Published: 6 December 2012
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Abstract

A series of macrocyclic imides and Schiff-bases have been prepared via the cyclocondensation of pyridine-2,6-dicarbonyl dichloride (1) with L-ornithine methyl ester to give the corresponding macrocyclic bisester 2. Treatment of 2 with hydrazine hydrate gave macrocyclic bisacid hydrazide 3, which was used as starting material. Condensation of bishydrazide 3 with diacid anhydrides or aromatic aldehydes in refluxing acetic acid or ethanol gave the corresponding macrocyclic bisimides 4, 5a,b and macrocyclic bis- hydrazones 6aj, respectively. The structure assignments of the new compounds were based on chemical and spectroscopic evidence. The antimicrobial screening showed that many of these newly synthesized compounds have good antimicrobial activities, comparable to ampicillin and ketaconazole used as reference drugs.
Keywords: macrocyclic polyamide candidates; amino acids; Schiff’s base; antimicrobial activity macrocyclic polyamide candidates; amino acids; Schiff’s base; antimicrobial activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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El-Salam, O.I.A.; Al-Omar, M.A.; Fayed, A.A.; Flefel, E.M.; Amr, A.E.-G. Synthesis of New Macrocyclic Polyamides as Antimicrobial Agent Candidates. Molecules 2012, 17, 14510-14521.

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