title: Synthesis and antimicrobial activity of novel 5-aminoimidazole-4-carboxamidrazones.
abstract: A mild and simple method was developed to prepare a series of fifteen 5-aminoimidazole 4-carboxamidrazones, starting from the easily accessible 5-amino-4-cyanoformimidoyl imidazoles. The antimicrobial activity of these novel amidrazones was screened against Gram positive (Staphylococcus aureus) and Gram negative (Escherichia coli, Pseudomonas aeruginosa) bacteria and Candida sp. (Candida albicans, Candida krusei, Candida parapsilosis). Only a subset of compounds displayed fair-moderate activity against S. aureus and E. coli but all exhibited activity against Candida sp. The three most potent antifungal compounds were further tested against Cryptococcus neoformans, Aspergillus fumigatus and three dermatophytes (Trichophyton rubrum, Trichophyton mentagrophytes, Microsporum gypseum). These three hit compounds strongly inhibited C. krusei and C. neoformans growth, although their activity on filamentous fungi was very weak when compared to the activity on yeasts.
authors.affiliation: Centre of Chemistry, Department of Chemistry, University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal.
authors.forename: Ana I
authors.initials: AI
authors.lastname: Ribeiro
authors.affiliation: FP-ENAS/CEBIMED, University Fernando Pessoa, 4200-150 Porto, Portugal.
authors.forename: Carla
authors.initials: C
authors.lastname: Gabriel
authors.affiliation: FP-ENAS/CEBIMED, University Fernando Pessoa, 4200-150 Porto, Portugal; CEQUIMED/Laboratory of Microbiology, Biological Sciences Department, Faculty of Pharmacy of University of Porto, 4050-313 Porto, Portugal. Electronic address: fatimaf@ufp.edu.pt.
authors.forename: Fátima
authors.initials: F
authors.lastname: Cerqueira
authors.affiliation: CEQUIMED/Laboratory of Microbiology, Biological Sciences Department, Faculty of Pharmacy of University of Porto, 4050-313 Porto, Portugal; Interdisciplinary Centre of Marine and Environmental Research (CIIMAR/CIMAR), University of Porto, 4050-123 Porto, Portugal.
authors.forename: Marta
authors.initials: M
authors.lastname: Maia
authors.affiliation: CEQUIMED/Laboratory of Microbiology, Biological Sciences Department, Faculty of Pharmacy of University of Porto, 4050-313 Porto, Portugal; Interdisciplinary Centre of Marine and Environmental Research (CIIMAR/CIMAR), University of Porto, 4050-123 Porto, Portugal.
authors.forename: Eugénia
authors.initials: E
authors.lastname: Pinto
authors.affiliation: FP-ENAS/CEBIMED, University Fernando Pessoa, 4200-150 Porto, Portugal.
authors.forename: João Carlos
authors.initials: JC
authors.lastname: Sousa
authors.affiliation: FP-ENAS/CEBIMED, University Fernando Pessoa, 4200-150 Porto, Portugal; Molecular Oncology GRP and Molecular Biology Laboratory-Virology Service, Portuguese Institute of Oncology (IPO), 4200-072 Porto, Portugal.
authors.forename: Rui
authors.initials: R
authors.lastname: Medeiros
authors.affiliation: Centre of Chemistry, Department of Chemistry, University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal.
authors.forename: M Fernanda
authors.initials: MF
authors.lastname: Proença
authors.affiliation: Centre of Chemistry, Department of Chemistry, University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal. Electronic address: ad@quimica.uminho.pt.
authors.forename: Alice M
authors.initials: AM
authors.lastname: Dias
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002175:Candida / Q000187:drug effects* / Q000254:growth & development; D004305:Dose-Response Relationship, Drug; D006090:Gram-Negative Bacteria / Q000187:drug effects* / Q000254:growth & development; D006094:Gram-Positive Bacteria / Q000187:drug effects* / Q000254:growth & development; D006835:Hydrazones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D006835:Hydrazones; D007093:Imidazoles
keywords: Amidrazone; Antifungal; Antimicrobial; Hydrazine; Imidazole