title: Synthesis, DNA binding and antitrypanosomal activity of benzimidazole analogues of DAPI.
abstract: A series of novel benzimidazole diamidines were prepared from the corresponding dicyano analogues either by applying Pinner methodology (5a-c, 10 and 13a) or by making amidoximes intermediates that were reduced to the corresponding amidines (15a-c). The new amidines were evaluated in vitro against the protozoan parasite Trypanosoma brucei rhodesiense (T. b. r.). The thiophene analogue 5b and the N-methyl compound 15a showed superior antitrypanosomal activity compared to that of the parent I.
authors.affiliation: Department of Chemistry, Georgia State University, Atlanta, GA 30303, United States; Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt. Electronic address: afarahat@gsu.edu.
authors.forename: Abdelbasset A
authors.initials: AA
authors.lastname: Farahat
authors.affiliation: Department of Chemistry, Georgia State University, Atlanta, GA 30303, United States.
authors.forename: Cheree
authors.initials: C
authors.lastname: Bennett-Vaughn
authors.affiliation: Department of Chemistry, Georgia State University, Atlanta, GA 30303, United States.
authors.forename: Ekaterina M
authors.initials: EM
authors.lastname: Mineva
authors.affiliation: Department of Chemistry, Georgia State University, Atlanta, GA 30303, United States.
authors.forename: Arvind
authors.initials: A
authors.lastname: Kumar
authors.affiliation: Swiss Tropical and Public Health Institute, Basel 4002, Switzerland; University of Basel, Basel 4003, Switzerland.
authors.forename: Tanja
authors.initials: T
authors.lastname: Wenzler
authors.affiliation: Swiss Tropical and Public Health Institute, Basel 4002, Switzerland; University of Basel, Basel 4003, Switzerland.
authors.forename: Reto
authors.initials: R
authors.lastname: Brun
authors.affiliation: Department of Chemistry, Georgia State University, Atlanta, GA 30303, United States.
authors.forename: Yang
authors.initials: Y
authors.lastname: Liu
authors.affiliation: Department of Chemistry, Georgia State University, Atlanta, GA 30303, United States.
authors.forename: W David
authors.initials: WD
authors.lastname: Wilson
authors.affiliation: Department of Chemistry, Georgia State University, Atlanta, GA 30303, United States.
authors.forename: David W
authors.initials: DW
authors.lastname: Boykin
mesh_terms: D000578:Amidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D001562:Benzimidazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001665:Binding Sites / Q000187:drug effects; D002478:Cells, Cultured; D004247:DNA / Q000187:drug effects*; D004305:Dose-Response Relationship, Drug; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D032446:Myoblasts / Q000187:drug effects; D021261:Parasitic Sensitivity Tests; D051381:Rats; D013329:Structure-Activity Relationship; D014344:Trypanocidal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D016833:Trypanosoma brucei rhodesiense / Q000187:drug effects*
chemical_list: D000578:Amidines; D001562:Benzimidazoles; D007211:Indoles; D014344:Trypanocidal Agents; C007293:DAPI; D004247:DNA; C031000:benzimidazole
keywords: Antitrypanosomal activity; Benzimidazole diamidines; DAPI; DNA minor groove binders