850. Bisdiguanides having antibacterial activity

Rose, F. L.; Swain, G.

doi:10.1039/jr9560004422

Cited by 64 publications

(28 citation statements)

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“…One is the reaction of N-(4-chlorophenyl)-cyanoguanidine in nitrobenzene at each of the amino groups of 1,6-hexamethylenediamine; alternatively, 1,6-di-(N 3 -cyano-N 1 -guanidino)hexane can be reacted with two equivalents of p-chloroaniline. 2 In the synthesis of Burns, 3 1,4-dicyanobutane was obtained by treatment of 1,4-dibromobutane with potassium cyanide. 1,6-Diaminohexane was precipitated as the HCl-salt after reduction of the cyanogroups.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of deuterium‐labelled chlorhexidine

Moser¹,

Hudlický²,

Sadeghi³

et al. 2007

Labelled Comp Radiopharmac

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The synthesis of deuterated chlorhexidine hydrochloride is reported. The specific labelling of the saturated chain is achieved through the combination of the previously reported synthesis of 2,2,3,3,4,4,5,5-( 2 H 8 )-hexane-1,6-diol and a synthesis of carbon-14 labelled chlorhexidine. This synthesis begins with commercially available hex-2,4-yne-1,6-diol, its protection as a bis-tetrahydropyranylether, and exhaustive deuterogenation under rhodium catalysis to produce, after acid hydrolysis of the protecting groups, the saturated octadeuterated 1,6-hexanediol. Conversion of this material in two steps to the corresponding 1,6-diaminohexane was followed by the generation of guanidines with dicyanimide and final condensation with p-chloroaniline. The title compound was obtained in 10 chemical steps and in 6% overall yield.

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Section: Resultsmentioning

confidence: 99%

Synthesis of deuterium‐labelled chlorhexidine

Moser¹,

Hudlický²,

Sadeghi³

et al. 2007

Labelled Comp Radiopharmac

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“…The low toxicity of biguanide compounds has been verified and currently biguanide biocides, such as chlorhexidine, are popularly used all over the world [4]. Since the pioneering works of Rose et al [5,6] the biguanide compounds have been widely used as effective antimicrobial agents owing to their broad spectra of activity, high kill rate and low mammalian toxicity [7,8]. Mouse (LD,.)…”

Section: Discussionmentioning

confidence: 99%

Self-Sterilizing Materials. 2 . Evaluation of Surface Antibacterial Activity

Ikeda

Yamaguchi

Tazuke

1986

Journal of Bioactive and Compatible Polymers

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The cross-linked polyacrylamide films containing covalently-bonded N'-4-(2-acryloyloxyethyl)phenyl-N 5 -4-chlorophenylbiguanide hydrochloride (CPF-2 ) exhibit antibacterial activity at their surfaces and successfully act as selfsterilizing materials. Scanning electron microscopy studies indicate that inoculated cells of E . coli and S . aureus onto CPF-2 films undergo morphological changes, such as shrinkage and deformation, while those inoculated on blank cross-linked films remain intact. These morphological changes were ascribed to the collapse of the bacterial cells due to the action of released N 1 -4-(2-hydroxyethyl)phenyl-N 5 -4-chlorophenylbiguanide hydrochloride from CPF-2 by hydrolysis. INTRODUCTIOÑ

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“…The first of these, exemplified by compound 1 (alexidine), is bisbiguanides. Reports of the antimicrobial activity of alexidine date back to the 1950s (56), and it has antifungal activity and has been assayed as a potential chemotherapeutic compound (57,58). Alexidine represents an interesting molecule for use in characterizing ODC more fully.…”

Section: Discussionmentioning

confidence: 99%

Discovery of Potent and Selective Inhibitors of Trypanosoma brucei Ornithine Decarboxylase

Smithson

Lee

Shelat

et al. 2010

Journal of Biological Chemistry

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Human African trypanosomiasis, caused by the eukaryotic parasite Trypanosoma brucei, is a serious health problem in much of central Africa. The only validated molecular target for treatment of human African trypanosomiasis is ornithine decarboxylase (ODC), which catalyzes the first step in polyamine metabolism. Here, we describe the use of an enzymatic high throughput screen of 316,114 unique molecules to identify potent and selective inhibitors of ODC. This screen identified four novel families of ODC inhibitors, including the first inhibitors selective for the parasitic enzyme. These compounds display unique binding modes, suggesting the presence of allosteric regulatory sites on the enzyme. Docking of a subset of these inhibitors, coupled with mutagenesis, also supports the existence of these allosteric sites.

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850. Bisdiguanides having antibacterial activity

Cited by 64 publications

References 0 publications

Synthesis of deuterium‐labelled chlorhexidine

Synthesis of deuterium‐labelled chlorhexidine

Self-Sterilizing Materials. 2 . Evaluation of Surface Antibacterial Activity

Discovery of Potent and Selective Inhibitors of Trypanosoma brucei Ornithine Decarboxylase

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