the synthesis of dicationic extended bis-benzimidazoles的合成dicationic bis-benzimidazoles扩展.pdfVIP

Molecules 2004, 9, 158-163 molecules ISSN 1420-3049 The Synthesis of Dicationic Extended Bis-Benzimidazoles Zhijan Kang 1, Christine C. Dykstra 2 and David W Boykin 1,* 1 Department of Chemistry Georgia State University, Atlanta, Georgia 30303, USA. Tel. +1-(404)- 651-3798, Fax +1-(404) 651-1416. 2 Department of Pathobiology, College of Veterinary Medicine, Auburn University, Auburn, Alabama 36849, USA. * Author to whom correspondence should be addressed; e-mail dboykin@ Received: 14 January 2004; in revised form: 26 January 2004 / Accepted: 27 January 2004 / Published: 28 February 2004 Abstract: The synthesis of extended dicationic bis-benzimidazoles starting from trans-1,2-bis(4-cyanophenyl)ethene and trans-1,2-bis(4-cyanophenyl)cyclopropane is reported. The target diamidines show significant in vitro activity against B. subtilis. Keywords: DIBAL reduction, benzimidazoles, amidines, Bacillus subtilis. Introduction Aromatic diamidines have a long history as antimicrobial agents [1]. Bis-benzimidazoles bearing amidino groups have been reported to show activity against a number of microorganisms. Flexible alkyl linked dicationic bis-benzimidazoles [2] and more ridged aryl linked bis-benzimidazoles are active in vivo against Pneumocystis carinii pneumonia in an immunosupressed rat model [3]. The later type molecules also show promising in vitro activity against several fungal organisms [4,5]. As part of a general program of development of aromatic diamidines as antimicrobial agents [1,6] we repo