title: Synthesis of new macrocyclic polyamides as antimicrobial agent candidates.
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 6a-j, 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.
authors.affiliation: Applied Organic Chemistry Department, National Research Center, Dokki 12622, Cairo, Egypt.
authors.forename: Osama I Abd
authors.initials: OI
authors.lastname: El-Salam
authors.forename: Mohamed A
authors.initials: MA
authors.lastname: Al-Omar
authors.forename: Ahmed A
authors.initials: AA
authors.lastname: Fayed
authors.forename: Eman M
authors.initials: EM
authors.lastname: Flefel
authors.forename: Abd El-Galil E
authors.initials: Ael-G
authors.lastname: Amr
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D006801:Humans; D047028:Macrocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009757:Nylons / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009952:Ornithine / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry; D012545:Schiff Bases / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D047028:Macrocyclic Compounds; D009757:Nylons; D011725:Pyridines; D012545:Schiff Bases; D009952:Ornithine