Synthesis, characterisation and anti-protozoal activity of carbamate-derived polyazamacrocycles.
A short, highly efficient approach for the synthesis of a novel class of polyazamacrocycles containing N-functionalised carbamate side-chains has been developed. The key steps involved a phase-transfer mediated macrocyclisation to form the ring system as well as a tin-catalysed reaction with isocyanates to introduce the carbamate side-chains. X-Ray crystallography confirmed successful formation of the 1,4,7,10-tetraazacyclododecane ring and N-functionalisation of all the amine centres. Preliminary testing of the biological activity of the compounds revealed significant anti-parasitic activity against bloodstream form African trypanosomes.
Wilson
Jennifer M
JM
WestCHEM, Department of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow, UK.
Giordani
Federica
F
Farrugia
Louis J
LJ
Barrett
Michael P
MP
Robins
David J
DJ
Sutherland
Andrew
A
D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002219:Carbamates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002460:Cell Line; D006801:Humans; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D021261:Parasitic Sensitivity Tests; D014346:Trypanosoma brucei brucei / Q000187:drug effects
D000981:Antiprotozoal Agents; D002219:Carbamates; D047028:Macrocyclic Compounds