ArticleEuropean journal of medicinal chemistry2008
Novel linear triaryl guanidines, N-substituted guanidines and potential prodrugs as antiprotozoal agents.
Article in European journal of medicinal chemistry, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 33 citations in OpenAlex.
- Guanidines: Privileged Scaffolds Against Neglected Tropical Diseases: A Review.Pharmaceuticals (Basel, Switzerland) · 2026Review
- Novel guanidine derivatives as mechanistic scaffolds for anticancer agents: synthesis, characterization, DNA-binding, and computational studies.RSC advances · 2025Article
- A Novel Prodrug Strategy Based on Reversibly Degradable Guanidine Imides for High Oral Bioavailability and Prolonged Pharmacokinetics of Broad-Spectrum Anti-influenza Agents.ACS central science · 2024Article
- Article
- Recent Advances in Developing Small Molecules Targeting Nucleic Acid.International journal of molecular sciences · 2016Review
- Structure-based DNA-targeting strategies with small molecule ligands for drug discovery.Medicinal research reviews · 2013Review
- In vitro and in vivo activities of dicationic diguanidino compounds against Echinococcus multilocularis metacestodes.Antimicrobial agents and chemotherapy · 2013Article
- State of the art in African trypanosome drug discovery.Current topics in medicinal chemistry · 2011Review
- The many twists and turns of DNA: template, telomere, tool, and target.Current opinion in structural biology · 2010Review
- Enhancing the intestinal absorption of molecules containing the polar guanidino functionality: a double-targeted prodrug approach.Journal of medicinal chemistry · 2010Article
- In vivo investigations of selected diamidine compounds against Trypanosoma evansi using a mouse model.Antimicrobial agents and chemotherapy · 2009Article
- Synthesis and SAR of alkanediamide-linked bisbenzamidines with anti-trypanosomal and anti-pneumocystis activity.Bioorganic & medicinal chemistry letters · 2009Article
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 2 countries.
Funding
Abstract
A series of triaryl guanidines and N-substituted guanidines designed to target the minor groove of DNA were synthesized and evaluated as antiprotozoal agents. Selected carbamate prodrugs of these guanidines were assayed for their oral efficacy. The linear triaryl bis-guanidines 6a,b were prepared from their corresponding diamines 4a,b through the intermediate BOC protected bis-guanidines 5a,b followed by acid catalyzed deprotection. The N-substituted guanidino analogues 9c-f were obtained in three steps starting by reacting the diamines 4a,b with ethyl isothiocyanatoformate to give the carbamoyl thioureas 7a,b. Subsequent condensation of 7a,b with various amines in the presence of EDCI provided the carbamoyl N-substituted guanidine intermediates 8a-f which can also be regarded as potential prodrugs for the guanidino derivatives. Compounds 9c-f were obtained via the base catalyzed decarbamoylation of 8a-f. The DNA binding affinities for the target dicationic bis-guanidines were assessed by DeltaT(m) values. In vitro antiprotozoal screening of the new compounds showed that derivatives 6a, 9c and 9e possess high to moderate activity against Trypanosoma brucei rhodesiense (T.b.r.) and Plasmodium falciparum (P.f.). While the prodrugs did not yield cures upon oral administration in the antitrypanosomal STIB900 mouse model, compounds 8a and 8c prolonged the survival of the treated mice.
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