Synthesis and antimicrobial activity studies of ortho-chlorodiarylamines and heteroaromatic tetracyclic systems in the benzo[b]thiophene series.
ortho-Chlorodiarylamines in the 2,3,7-trimethylbenzo[b]thiophene series were prepared in high yields (70-85%) by C-N palladium-catalyzed cross-coupling using P(t-Bu)(3) as ligand and NaOt-Bu as base. A palladium-assisted C-C intramolecular cyclization of the coupling products gave thienocarbazoles and the dechlorinated diarylamines. Studies of antimicrobial activity of the compounds obtained, against representative species of bacteria (Escherichia coli, Pseudomonas aeruginosa, Bacillus cereus and Bacillus subtilis) and fungi (Candida albicans), were performed. We have also included in the biological assays some pyridine derivatives previously prepared by us, and it was possible to establish some structure-activity relationships (SARs).
Queiroz
Maria-João R P
MJ
Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal. mjrpq@quimica.uminho.pt
Ferreira
Isabel C F R
IC
De Gaetano
Yannick
Y
Kirsch
Gilbert
G
Calhelha
Ricardo C
RC
Estevinho
Letícia M
LM
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D066298:In Vitro Techniques; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000588:Amines; D000890:Anti-Infective Agents; D013876:Thiophenes; C088015:benzothiophene