Imidazoles from nitroallylic acetates and α-bromonitroalkenes with amidines: synthesis and trypanocidal activity studies.
Cascade reactions of amidines with nitroallylic acetates and α-bromonitroalkenes provide potentially bioactive imidazoles in good to excellent yields in most cases. While 2,4-disubstituted imidazol-5-yl acetates are formed in the first case, 2,4-disubstituted imidazoles, bearing no substituent at position 5, are the products in the second case. These two series of imidazoles, viz. 2,4,5-trisubstituted and 2,4-disubstituted, were screened for their activity against the protozoan parasite Trypanosoma cruzi which is responsible for Chagas disease. As many as three compounds were as active as the standard benznidazole and two others were 2-3-fold more active highlighting the potential of substituted imidazoles, easily accessible from nitroalkenes, as possible anti-parasitic agents.
Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400 076, India. irishi@iitb.ac.in.
Elumalai
E
Gopi
Tarun
T
Kumar
Rubem F S
RF
Menna-Barreto
Wagner O
WO
Valença
Eufrânio N
EN
da Silva Júnior
Irishi N N
IN
Namboothiri
D000085:Acetates / Q000737:chemistry*; D000578:Amidines / Q000737:chemistry*; D000818:Animals; D014355:Chagas Disease / Q000188:drug therapy* / Q000469:parasitology; D004305:Dose-Response Relationship, Drug; D007093:Imidazoles / Q000737:chemistry*; D051379:Mice; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D021261:Parasitic Sensitivity Tests; D013329:Structure-Activity Relationship; D014344:Trypanocidal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D014349:Trypanosoma cruzi / Q000187:drug effects*
D000085:Acetates; D000578:Amidines; D007093:Imidazoles; D009574:Nitro Compounds; D014344:Trypanocidal Agents; C029899:imidazole