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Diguanidino and "reversed" diamidino 2,5-diarylfurans as antimicrobial agents.
Stephens, C E; Tanious, F; Kim, S; Wilson, W D; Schell, W A; Perfect, J R; Franzblau, S G; Boykin, D W.
Afiliação
  • Stephens CE; Department of Chemistry, Georgia State University, 1 University Plaza, Atlanta, Georgia 30303-3083, USA.
J Med Chem ; 44(11): 1741-8, 2001 May 24.
Article em En | MEDLINE | ID: mdl-11356109
Dicationic 2,5-bis(4-guanidinophenyl)furans 5a-5f, 2,5-bis[4-(arylimino)aminophenyl]furans 6a-6b and 6e-6k, and 2,5-bis[4-(alkylimino)aminophenyl]furans 6c-6d have been synthesized starting from 2,5-bis[tri-n-butylstannyl]furan. Thermal melting studies with poly dA*dT and the duplex oligomer d(CGCGAATTCGCG)2 demonstrated high DNA binding affinities for a number of the compounds. The binding affinities are highly dependent on structure and are significantly affected by substituents both on the phenyl rings of the 2,5-diphenylfuran nucleus and on the cationic centers. Of the 17 novel dicationic compounds synthesized, six (6a, 6b, 5b, 6f, 6h, 6i) exhibited MICs of 2 microg/mL or less versus Mycobacterium tuberculosis. Of the compounds screened against Candida albicans, three gave MICs of 2 microg/mL or less (5b, 6h, 6i), and two (5b, 6i) were fungicidal, unlike a standard antifungal drug fluconazole, which was fungistatic. In addition, one of the tested compounds (6i) exhibited a MIC of <1 microg/mL against Aspergillus fumigatus, while also being a fungicidal against this organism. Finally, when evaluated against an expanded fungal panel, compound 6h showed good activity against Cryptococcus neoformans and Rhizopus arrhizus.
Assuntos
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Coleções: 01-internacional Contexto em Saúde: 3_ND Base de dados: MEDLINE Assunto principal: Furanos / Amidinas / Aminopiridinas / Antibacterianos Idioma: En Revista: J Med Chem Ano de publicação: 2001 Tipo de documento: Article
Buscar no Google
Coleções: 01-internacional Contexto em Saúde: 3_ND Base de dados: MEDLINE Assunto principal: Furanos / Amidinas / Aminopiridinas / Antibacterianos Idioma: En Revista: J Med Chem Ano de publicação: 2001 Tipo de documento: Article